MCF-7, MDA-MB-231, MEF and cells were obtained from ATCC and cultured in DMEM (Corning) supplemented with 10% FBS, 100 units/mL streptomycin and 100 μg/mL penicillin. K562 cells were grown in RPMI-1640 with 25Mm HEPES and 2.0 g/L NaHCO3 in 10 % FBS, 2 mM glutamine, 100 units/mL streptomycin and 100 μg/mL penicillin. Cell authentication was performed by ATCC using short tandem repeat analysis. All cells were maintained in a 37 ºC and 5% CO2 humidified incubator, used for < 20 passages following thawing, and cultured for no longer than 3 months.
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Benzothiazole
Benzothiazole
Benzothiazole is a heterocyclic aromatic compound consisting of a benzene ring fused to a thiazole ring.
It is used in the synthesis of various pharmaceuticals, dyes, and other industrial chemicals.
Benzothiazole and its derivatives have been reported to exhibit a wide range of biological activities, including antimicrobial, antifungal, antiinflammatory, and antitumor properties.
Resaerchers utilize benzothiazole compounds in a variety of applications, from medical treatements to materials science.
Optimizing the research process for benzothiazole can be facilitated by powerful AI-driven tools like PubCompare.ai, which help identify the best protocols and products from the literature, preprints, and patents to enhance reproducibility and streamline the research workflow.
It is used in the synthesis of various pharmaceuticals, dyes, and other industrial chemicals.
Benzothiazole and its derivatives have been reported to exhibit a wide range of biological activities, including antimicrobial, antifungal, antiinflammatory, and antitumor properties.
Resaerchers utilize benzothiazole compounds in a variety of applications, from medical treatements to materials science.
Optimizing the research process for benzothiazole can be facilitated by powerful AI-driven tools like PubCompare.ai, which help identify the best protocols and products from the literature, preprints, and patents to enhance reproducibility and streamline the research workflow.
Most cited protocols related to «Benzothiazole»
Bicarbonate, Sodium
Cells
Glutamine
HEPES
K562 Cells
Penicillins
Short Tandem Repeat
Streptomycin
1H NMR
Carbon-13 Magnetic Resonance Spectroscopy
High-Performance Liquid Chromatographies
Mass Spectrometry
Solvents
Triplets
Amines
benzimidazole
benzothiazole
compound 17
compound 20
compound 21
compound 26
DNA Library
maribavir
NS8593
Riluzole
Thiazoles
Thiones
Metabolic activity of viable cells was measured by MTT assay based on the reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium salt to a formazan product, which can be quantified spectrophotometrically to determine the percent of viable cells [32 (link)].
Anticancer activities of new benzothiazole acylhydrazones derivatives were evaluated against A549 C6, MCF-7 and HT-29 cell lines. The selectivity of their cytotoxic effects was evaluated on NIH/3T3 mouse embryonic fibroblast cells. NIH/3T3 cells were incubated in DMEM supplemented with fetal calf serum, penicillin (100 IU/mL), streptomycin (100 mg/mL) and 7.5% NaHCO3 at 37 °C in a humidified atmosphere of 95% air and 5% CO2. Carcinogenic cells were incubated in RPMI medium supplemented with fetal calf serum, penicillin (100 IU/mL), streptomycin (100 mg/mL) and 7.5% NaHCO3 at 37 °C in a humidified atmosphere of 95% air and 5% CO2. All cell lines were seeded at a density of 1 × 104 cells into the 96-well plates. After 24 h of incubating period, the culture mediums were removed and test compounds were added at concentrations of 0.000316–1 mM. After a 24 h incubation period, OD of samples were measured by a microplate reader (Biotek, Winooski, VT, USA) at 540 nm. Inhibition % at concentrations was determined using the formula below and IC50 values were calculated by nonlinear regression analysis using the SigmaPlot v.10 package program (Manufacturer, City, US State abbrev. if applicable, Country) [33 (link),34 (link),35 (link),36 (link)]. Cisplatin was used as a positive control:
Anticancer activities of new benzothiazole acylhydrazones derivatives were evaluated against A549 C6, MCF-7 and HT-29 cell lines. The selectivity of their cytotoxic effects was evaluated on NIH/3T3 mouse embryonic fibroblast cells. NIH/3T3 cells were incubated in DMEM supplemented with fetal calf serum, penicillin (100 IU/mL), streptomycin (100 mg/mL) and 7.5% NaHCO3 at 37 °C in a humidified atmosphere of 95% air and 5% CO2. Carcinogenic cells were incubated in RPMI medium supplemented with fetal calf serum, penicillin (100 IU/mL), streptomycin (100 mg/mL) and 7.5% NaHCO3 at 37 °C in a humidified atmosphere of 95% air and 5% CO2. All cell lines were seeded at a density of 1 × 104 cells into the 96-well plates. After 24 h of incubating period, the culture mediums were removed and test compounds were added at concentrations of 0.000316–1 mM. After a 24 h incubation period, OD of samples were measured by a microplate reader (Biotek, Winooski, VT, USA) at 540 nm. Inhibition % at concentrations was determined using the formula below and IC50 values were calculated by nonlinear regression analysis using the SigmaPlot v.10 package program (Manufacturer, City, US State abbrev. if applicable, Country) [33 (link),34 (link),35 (link),36 (link)]. Cisplatin was used as a positive control:
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Atmosphere
benzothiazole
Bicarbonate, Sodium
Biological Assay
Carcinogens
Cell Lines
Cells
Cisplatin
Culture Media
derivatives
Embryo
Fetal Bovine Serum
Fibroblasts
Formazans
Genetic Selection
HT29 Cells
Mus
NIH 3T3 Cells
Penicillins
Psychological Inhibition
Salts
Streptomycin
Most recents protocols related to «Benzothiazole»
A substantial quantity of 2-phenol-benzothiazole must be synthesized. Benzothiazole (1 mmol), 2-hydroxyiodobenzene (1 mmol), and K2CO3 (2 mmol) as a binding agent were combined in 2 mL of DMSO. The resulting mixture is magnetically stirred at 120°C for 6 h, with the reaction progress monitored via TLC. Upon completion, the reaction mixture was cooled to room temperature, and the solvent is evaporated under reduced pressure. Following this, water (8 mL) and an equivalent volume of ethyl acetate were introduced for extraction through multiple iterations of small-volume extractions (3 times). The aqueous layer was discarded, and the organic layer was desiccated with Na2SO4. Subsequent to drying, the organic layer underwent evaporation under reduced pressure, and the resulting residue was subjected to column chromatography. Intermediate 1 was extracted through column chromatography using a mobile phase of petroleum ether: ethyl acetate = 2:1. The yield is 50%, and the product was dried in an oven for subsequent use.
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Example 1
A solution of tert-butyl (R)-(1-(5-(2-chloropyrimidine-4-carboxamido)-2-methylbenzo[d]thiazol-4-yl)pyrrolidin-3-yl)carbamate (Intermediate 2, 25.2 mg, 0.052 mmol) in 1,4-dioxane (0.7 mL) was treated with (2,6-difluorophenyl)boronic acid (16.3 mg, 0.103 mmol), XPhos Pd G2 (7.5 mg), potassium phosphate tribasic (21.8 mg, 0.103 mmol), and water (0.1 mL). The reaction mixture was then sparged with nitrogen, sealed, and stirred at 80° C. overnight. After cooling to r.t., the reaction mixture was concentrated and TFA (1 mL) was added and the resulting mixture was stirred at r.t. for 30 minutes. The reaction mixture was then diluted with acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C23H21F2N6OS (M+H)+: m/z=467.1; Found 467.2. 1H NMR (500 MHz, DMSO-d6) δ 11.23 (s, 1H), 9.34 (d, J=5.0 Hz, 1H), 8.55 (d, J=8.8 Hz, 1H), 8.31-8.15 (m, 4H), 7.95 (d, J=8.8 Hz, 1H), 7.71 (tt, J=8.4, 6.4 Hz, 1H), 7.39 (t, J=8.4 Hz, 2H), 3.81 (s, 1H), 3.69-3.59 (m, 2H), 3.53 (q, J=8.2 Hz, 1H), 3.34-3.24 (m, 1H), 2.85 (s, 3H), 2.24-2.14 (m, 1H), 2.08-1.98 (m, 1H).
Example 2
This compound was prepared according to the procedures described in Example 1, using (2-fluoro-6-methylphenyl)boronic acid instead of (2,6-difluorophenyl)boronic acid as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C24H24FN6OS (M+H)+: m/z=463.2; Found: 463.2. 1H NMR (500 MHz, DMSO-d6) δ 11.22 (s, 1H), 9.33 (d, J=5.0 Hz, 1H), 8.52 (d, J=8.8 Hz, 1H), 8.19 (d, J=5.0 Hz, 1H), 8.16 (br s, 3H), 7.95 (d, J=8.8 Hz, 1H), 7.50 (td, J=8.0, 5.8 Hz, 1H), 7.28 (m, 2H), 3.70 (s, 1H), 3.65-3.58 (m, 2H), 3.52 (q, J=8.4 Hz, 1H), 3.25 (td, J=8.4, 3.8 Hz, 1H), 2.84 (s, 3H), 2.30 (s, 3H), 2.12-2.01 (m, 1H), 2.00-1.91 (m, 1H).
Example 3
This compound was prepared according to the procedures described in Example 1, using (2-fluoro-6-(trifluoromethyl)phenyl)boronic acid instead of (2,6-difluorophenyl)boronic acid as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C24H21F4N6OS (M+H)+: m/z=517.1; Found: 517.1.
Example 4
This compound was prepared according to the procedures described in Example 1, using tert-butyl (3-fluoro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)(methyl)carbamate (Intermediate 3) instead of (2,6-difluorophenyl)boronic acid as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C26H29FN7S (M+H)+: m/z=506.2; Found: 506.3. 1H NMR (500 MHz, DMSO-d6) δ 11.19 (s, 1H), 9.33 (d, J=5.0 Hz, 1H), 9.15 (br s, 2H), 8.49 (d, J=8.8 Hz, 1H), 8.32 (br s, 2H), 8.20 (d, J=5.0 Hz, 1H), 7.94 (d, J=8.8 Hz, 1H), 7.42 (d, J=10.1 Hz, 1H), 7.38 (s, 1H), 4.24 (s, 2H), 3.73-3.66 (m, 1H), 3.65-3.59 (m, 2H), 3.53 (q, J=8.4 Hz, 1H), 3.26 (td, J=8.4, 3.8 Hz, 1H), 2.84 (s, 3H), 2.64 (s, 3H), 2.31 (s, 3H), 2.14-1.94 (m, 2H).
Example 11
Example 12
Example 13
This compound was prepared according to the procedures described in Example 12, using 4-chloro-2-isopropyl-5-nitrobenzo[d]thiazole (Intermediate 12) instead of 4-chloro-2-ethyl-5-nitrobenzo[d]thiazole (Intermediate 11) as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C27H30FN6O3S (M+H)+: m/z=537.2; Found: 537.1.
Example 16
HATU (15 mg, 0.040 mmol) was added to a solution of tert-butyl ((3R,5S)-1-(5-amino-2-methylbenzo[d]thiazol-4-yl)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (Intermediate 10, 15 mg, 0.040 mmol), 2-(2,3-difluoro-6-methoxyphenyl)pyrimidine-4-carboxylic acid (Intermediate 14, 10.6 mg, 0.040 mmol) and triethylamine (0.01 mL, 0.072 mmol) in DMF (1 mL). The reaction mixture was stirred at 50° C. for 30 minutes. After cooling to r.t., water was added and the precipitated product was collected via filtration, washed with water, and air dried. The solid residue was then dissolved in TFA and the resultant solution was stirred at r.t. for 30 minutes. The reaction mixture was then diluted with acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C25H25F2N6O3S (M+H)+: m/z=527.2; Found: 527.1. 1H NMR (500 MHz, DMSO-d6) δ 11.46 (s, 1H), 9.32 (d, J=5.0 Hz, 1H), 8.56 (d, J=8.8 Hz, 1H), 8.26 (br s, 3H), 8.20 (d, J=5.0 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.64 (q, J=9.4 Hz, 1H), 7.07 (ddd, J=9.4, 3.6, 1.7 Hz, 1H), 4.44 (t, J=5.0 Hz, 1H), 4.00 (qd, J=7.3, 5.0 Hz, 1H), 3.78 (s, 3H), 3.70-3.60 (m, 1H), 3.55 (dd, J=10.4, 5.8 Hz, 1H), 3.24-3.17 (m, 1H), 3.17-3.11 (m, 1H), 2.87 (s, 3H), 2.34-2.26 (m, 1H), 1.84-1.75 (m, 1H).
Example 17
This compound was prepared according to the procedures described in Example 16, using 2-(3-cyano-2-fluoro-6-(methoxy-d3)phenyl)pyrimidine-4-carboxylic acid (Intermediate 15) instead of 2-(2,3-difluoro-6-methoxyphenyl)pyrimidine-4-carboxylic acid (Intermediate 14) as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C26H22D3FN7O3S (M+H)+: m/z=537.2; Found: 537.2.
Example 18
A solution of N-(4-((2S,4R)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-2-methylbenzo[d]thiazol-5-yl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide (Example 11, 57 mg, 0.11 mmol) in 1,2-DCE (1 mL) was treated with acetone (0.02 mL, 0.27 mmol), acetic acid (0.02 mL, 0.35 mmol), and sodium triacetoxyborohydride (47.5 mg, 0.224 mmol). The reaction mixture was then stirred at r.t. overnight. Water was then added and the reaction mixture was concentrated under vacuum, diluted with acetonitrile, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C2H32FN6O3S (M+H)+: m/z=551.2; Found: 551.2. 1H NMR (600 MHz, DMSO-d6) δ 11.46 (s, 1H), 9.29 (d, J=5.0 Hz, 1H), 8.97 (br d, J=79.1 Hz, 2H), 8.60 (d, J=8.8 Hz, 1H), 8.17 (d, J=5.0 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.57 (td, J=8.5, 6.9 Hz, 1H), 7.09 (d, J=8.5 Hz, 1H), 7.02 (t, J=8.8 Hz, 1H), 4.49 (t, J=5.2 Hz, 1H), 4.12 (tt, J=8.0, 5.2 Hz, 1H), 3.78 (s, 3H), 3.55-3.46 (m, 2H), 3.46-3.39 (m, 1H), 3.21-3.11 (m, 3H), 2.84 (s, 3H), 2.33-2.25 (m, 1H), 1.99-1.91 (m, 1H), 1.13 (dd, J=22.8, 6.4 Hz, 6H).
Example 19
This compound was prepared according to the procedures described in Example 18, using tetrahydro-4H-pyran-4-one instead of acetone as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C3H34FN6O4S (M+H)+: m/z=593.2; Found: 593.2.
Example 20
A solution of N-(4-((2S,4R)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-2-methylbenzo[d]thiazol-5-yl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide (Example 11, 38 mg, 0.075 mmol) in DMF (1 mL) was treated with a 0.1 M stock solution of acetic acid (0.75 mL, 0.075 mmol) in THF, HATU (28.4 mg, 0.075 mmol), and triethylamine (0.04 mL, 0.287 mmol). The reaction mixture was stirred at 50° C. for 30 minutes. After cooling to r.t., the reaction mixture was concentrated slightly, water was added and the precipitated product was collected via filtration, washed with water, and air dried. The crude material was then dissolved in acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C27H28FN6O4S (M+H)+: m/z=551.2; Found: 551.2.
Example 21
A solution of N-(4-((2S,4R)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-2-methylbenzo[d]thiazol-5-yl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide(Example 11, 38 mg, 0.075 mmol) and triethylamine (8 mg, 0.079 mmol) in anhydrous THF (2 mL) was treated with a 0.1 M solution of methanesulfonyl chloride (0.75 mL, 0.075 mmol) in anhydrous THF. The reaction mixture was stirred at r.t. for 15 minutes. The reaction was then treated with water, and the resulting mixture was diluted with acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C26H28FN6O5S2 (M+H)+: m/z=587.2; Found: 587.1. 1H NMR (600 MHz, DMSO-d6) δ 11.64 (s, 1H), 9.28 (d, J=5.0 Hz, 1H), 8.58 (d, J=8.8 Hz, 1H), 8.16 (d, J=5.0 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.57 (td, J=8.4, 6.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.02 (t, J=8.8 Hz, 1H), 4.31 (br s, 1H), 3.93-3.85 (m, 1H), 3.75-3.83 (m, 4H), 3.44 (dd, J=9.5, 5.8 Hz, 1H), 3.21 (dd, J=9.5, 5.8 Hz, 1H), 3.19-3.08 (m, 2H), 2.86 (s, 6H), 2.18-2.10 (m, 1H), 1.75-1.67 (m, 1H).
Example 22
This compound was prepared according to the procedures described in Example 11, using (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C25H23FN5O3S (M+H)+: m/z=492.2; Found: 492.2.
Example 23
This compound was prepared according to the procedures described in Example 11, using tert-butyl ((3S,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C25H26FN6O3S (M+H)+: m/z=509.2; Found: 509.2.
Example 24
This compound was prepared according to the procedures described in Example 11, using N-methyl-1-(1-methylpyrrolidin-3-yl)methanamine instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C27H30FN6O2S (M+H)+: m/z=521.2; Found: 521.3.
Example 26
This compound was prepared according to the procedures described in Example 11, using tert-butyl (S)-(morpholin-3-ylmethyl)carbamate instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C25H26FN6O3S (M+H)+: m/z=509.2; Found: 509.2.
Example 27
This compound was prepared according to the procedures described in Example 11, using tert-butyl (R)-3-(methylamino)piperidine-1-carboxylate instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C26H28FN6O2S (M+H)+: m/z=507.2; Found: 507.2.
Example 28
This compound was prepared according to the procedures described in Example 11, using tert-butyl octahydro-6H-pyrrolo[2,3-c]pyridine-6-carboxylate instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C27H28FN6O2S (M+H)+: m/z=519.2; Found: 519.2.
Example 29
This compound was prepared according to the procedures described in Example 11, using 2-(pyrrolidin-3-yl)pyridine instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C29H26FN6O2S (M+H)+: m/z=541.2; Found: 541.2.
Example 30
This compound was prepared according to the procedures described in Example 11, using (S)-(4,4-difluoropyrrolidin-2-yl)methanol instead of tert-butyl ((3R,5S)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate as starting material. LCMS calculated for C25H23F3N5O3S (M+H)+: m/z=530.2; Found: 530.2.
Example 31
This compound was prepared according to the procedures described in Example 11, using tert-butyl (1S,4S)-5-(5-amino-2-methylbenzo[d]thiazol-4-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (Intermediate 17) instead of tert-butyl ((3R,5S)-1-(5-amino-2-methylbenzo[d]thiazol-4-yl)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (Intermediate 10) and 2-(2,6-difluorophenyl)pyrimidine-4-carboxylic acid (Intermediate 16) instead of 2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxylic acid (Intermediate 4) as starting materials. LCMS calculated for C25H23F2N6OS (M+H)+: m/z=493.2; Found: 493.2.
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Example 9
Example 10
This compound was prepared according to the procedures described in Example 9, using (S)-tert-butyl (1-(3-fluoro-2-(3-methoxypropanamido)-6-nitrophenyl)pyrrolidin-2-yl)methylcarbamate (Intermediate 8) instead of (S)-tert-butyl (1-(3-fluoro-2-(2-methoxyacetamido)-6-nitrophenyl)pyrrolidin-2-yl)methylcarbamate (Intermediate 7) as starting material. Purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C27H30FN6O3S (M+H)+: m/z=537.2; Found: 537.2. 1H NMR (500 MHz, DMSO-d6) δ 11.54 (s, 1H), 9.30 (d, J=5.0 Hz, 1H), 8.57 (d, J=8.8 Hz, 1H), 8.17 (d, J=5.0 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H), 7.66 (t, J=5.6 Hz, 3H), 7.59 (td, J=8.5, 6.9 Hz, 1H), 7.10 (d, J=8.5 Hz, 1H), 7.03 (m, 1H), 4.14-4.06 (m, 1H), 3.84-3.73 (m, 5H), 3.35 (t, J=6.1 Hz, 2H), 3.31 (s, 3H), 3.26-3.16 (m, 2H), 2.64-2.54 (m, 1H), 2.46-2.37 (m, 1H), 2.30-2.21 (m, 1H), 2.00-1.90 (m, 1H), 1.73-1.57 (m, 2H).
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1H NMR
acetonitrile
benzothiazole
Lincomycin
methyl carbamate
Sulfoxide, Dimethyl
TERT protein, human
Ethyl 2-(2-(benzo[d]thiazol-2-yl)phenoxy)acetate (A1 ) White solid; Yield/%: 78%; Mp/°C: 73.4∼75.4; ESI-MS [M + H]+: 314.6; 1H NMR (600 MHz, CDCl3) δ ppm: 8.556 (d, J = 7.8 Hz, 1H, Ph-H), 8.096 (d, J = 8.2 Hz, 1H, Ph-H), 7.935 (d, J = 8.0 Hz, 1H, Ph-H), 7.491 (t, J = 7.68 Hz, 1H, Ph-H), 7.439 (t, J = 7.86 Hz, 1H, Ph-H), 7.377 (t, J = 7.62 Hz, 1H, Ph-H), 7.199 (t, J = 7.56 Hz, 1H, Ph-H), 6.969 (d, J = 8.28 Hz, 1H, Ph-H), 4.866 (s, 2H, -OCH2), 4.299–4.335 (m, 2H, CH2), 1.316 (t, J = 7.14 Hz, 3H, CH3). 13C NMR (150 MHz, CDCl3) δ ppm: 168.2 (-C=O), 163.1 (thiazole-C), 155.6 (benzothiazole-C), 136.3 (benzothiazole-C), 131.9 (Ph-C), 130.2 (Ph-C), 126.1 (Ph-C), 124.9 (Ph-C), 122.9 (Ph-C), 122.4 (Ph-C), 121.4 (Ph-C), 112.6 (Ph-C), 66.1 (-OCH2COOCH2CH3), 61.7(-OCH2COOCH2CH3), 14.3(-OCH2COOCH2CH3). Anal. Calcd for C17H15NO3S: C, 65.16%; H, 4.82%; N, 4.47%; Found: C, 65.18%; H, 4.83%; N, 4.46%.
2-(2-((2-nitrobenzyl)oxy)phenyl)benzo[d]thiazole (A2 ) White solid; Yield/%: 81%; Mp/°C: 115.6∼117.6; ESI-MS [M + H]+: 363.2; 1H NMR (600 MHz, CDCl3) δ ppm: 8.502 (d, J = 7.8 Hz, 1H, Ph-H), 8.231 (d, J = 8.22 Hz, 1H, Ph-H), 8.115 (d, J = 8.16 Hz, 1H, Ph-H), 7.971 (d, J = 7.86 Hz, 1H, Ph-H), 7.905 (d, J = 7.92 Hz, 1H, Ph-H), 7.687 (t, J = 7.5 Hz, 1H, Ph-H), 7.496–7.547 (m, 2H, Ph-H), 7.373–7.440 (m, 2H, Ph-H), 7.182 (t, J = 7.5 Hz, 1H, Ph-H), 7.036 (d, J = 8.34 Hz, 1H, Ph-H), 5.792 (s, 2H, -OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 163.1 (thiazole-C), 155.8 (benzothiazole-C), 152.3 (Ph-C), 147.1 (Ph-C), 136.0 (Ph-C), 134.3 (Ph-C), 133.3 (benzothiazole-C), 132.0 (Ph-C), 130.4 (Ph-C), 129.1 (Ph-C), 128.8 (Ph-C), 126.2 (Ph-C), 125.3 (Ph-C), 125.0 (Ph-C), 123.0 (Ph-C), 122.2 (Ph-C), 121.4 (Ph-C), 113.4 (Ph-C), 68.2(-OCH2-). Anal. Calcd for C20H14N2O3S: C, 66.29%; H, 3.89%; N, 7.73%; Found: C, 66.31%; H, 3.88%; N, 7.74%.
2-(3-(2-(benzo[d]thiazol-2-yl)phenoxy)propyl)isoindoline-1,3-dione (A3 ) Pale yellow solid; Yield/%: 67%; Mp/°C: 141.6∼143.6; ESI-MS[M + H]+: 415.1; 1H NMR (600 MHz, CDCl3) δ ppm: 8.476 (dd, J = 7.8, 1.8 Hz, 1H, Ph-H), 8.033 (d, J = 8.4 Hz, 1H, Ph-H), 7.978 (d, J = 8.4 Hz, 1H, Ph-H), 7.721–7.735 (m, 2H, Ph-H), 7.585–7.599 (m, 2H Ph-H), 7.421–7.486 (m, 2H, Ph-H), 7.374 (t, J = 7.8 Hz, 1H, Ph-H), 7.115 (t, J = 7.68 Hz, 1H, Ph-H), 7.033 (d, J = 8.4 Hz, 1H, Ph-H), 4.319 (t, J = 5.88 Hz, 2H, -OCH2), 4.080 (t, J = 6.84 Hz, 2H, -CH2), 2.418–2.460 (m, 2H, -CH2). 13C NMR (150 MHz, CDCl3) δ ppm: 168.5 (-C=O), 163.3 (thiazole-C), 156.5 (benzothiazole-C), 135.9 (benzothiazole-C), 133.9 (Ph-C), 132.1 (Ph-C), 129.8 (Ph-C), 126.1 (Ph-C), 124.8 (Ph-C), 123.1 (Ph-C), 122.6 (Ph-C), 121.6 (Ph-C), 112.2 (Ph-C), 67.3 (-OCH2CH2CH2-), 36.1 (-OCH2CH2CH2-), 28.8 (-OCH2CH2CH2-). Anal. Calcd for C24H18N2O3S: C, 69.55%; H, 4.38%; N, 6.76%; Found: C,69.51%; H, 4.37%; N, 6.75%.
2-(2-((4-nitrobenzyl)oxy)phenyl)benzo[d]thiazole (A4 ) White solid; Yield/%: 70%; Mp/°C: 135.5∼137.5; ESI-MS [M + H]+: 363.2; 1H NMR (600 MHz, CDCl3) δ ppm: 8.535 (dd, J = 8.16, 2.4 Hz, 1H, Ph-H), 8.287 (d, J = 8.58 Hz, 2H, Ph-H), 8.101 (d, J = 8.16 Hz, 1H, Ph-H), 7.897 (d, J = 7.98 Hz, 1H, Ph-H), 7.733 (d, J = 8.58 Hz, 2H, Ph-H), 7.503 (t, J = 7.86 Hz, 1H, Ph-H), 7.370–7.454 (m, 2H, Ph-H), 7.184 (t, J = 7.62 Hz, 1H, Ph-H), 7.057 (d, J = 8.28 Hz, 1H, Ph-H), 5.426 (s, 2H,-OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 162.9 (thiazole-C), 155.8 (benzothiazole-C), 148.0 (Ph-C), 143.4 (Ph-C), 135.8 (Ph-C), 132.1 (benzothiazole-C), 130.4 (Ph-C), 128.3 (Ph-C), 126.3 (Ph-C), 125.1 (Ph-C), 124.1 (Ph-C), 122.9 (Ph-C), 122.2 (Ph-C), 121.4 (Ph-C), 113.0 (Ph-C), 69.9 (-OCH2-). Anal. Calcd for C20H14N2O3S: C, 66.29%; H, 3.89%; N, 7.73%; Found: C, 66.30%; H, 3.90%; N, 7.75%.
2-(2-((3-chlorobenzyl)oxy)phenyl)benzo[d]thiazol (A5 ) White solid; Yield/%: 65%; Mp/°C: 53.4∼55.4; ESI-MS [M + H]+: 352.1; 1H NMR (600 MHz, CDCl3) δ ppm: 8.546 (dd, J = 7.68, 1.38 Hz, 1H, Ph-H), 8.098 (d, J = 8.10 Hz, 1H, Ph-H), 7.899 (d, J = 7.92 Hz, 1H, Ph-H), 7.567 (s, 1H, Ph-H), 7.491 (t, J = 8.04 Hz, 1H, Ph-H), 7.347–7.429 (m, 5H, Ph-H), 7.158 (t, J = 7.74 Hz, 1H, Ph-H), 7.069 (d, J = 8.34 Hz, 1H, Ph-H), 5.311 (s, 2H, -OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 156.1 (thiazole-C), 138.3 (Ph-C) (benzothiazole-C), 136.1 (Ph-C), 134.7 (benzothiazole-C), 131.9 (Ph-C), 130.1 (Ph-C), 128.5 (Ph-C), 127.9 (Ph-C), 126.1 (Ph-C), 125.9 (Ph-C), 124.8 (Ph-C), 122.9 (Ph-C), 121.8 (Ph-C), 121.4 (Ph-C), 113.0 (Ph-C), 70.4 (-OCH2-). Anal. Calcd for C20H14ClNOS: C, 68.27%; H, 4.01%; N, 3.98%; Found: C, 68.28%; H, 4.02%; N, 3.99%.
2-(2-((4-methylbenzyl)oxy)phenyl)benzo[d]thiazole (A6 ) White solid; Yield/% 77%; Mp/°C: 57.3∼59.3; ESI-MS [M + H]+: 332.0; 1H NMR (600 MHz, CDCl3) δ ppm: 8.555 (dd, J = 7.98, 1.32 Hz, 1H, Ph-H), 8.082 (d, J = 8.16Hz, 1H, Ph-H), 7.883 (d, J = 7.92Hz, 1H, Ph-H), 7.402–7.489 (m, 4H, Ph-H), 7.351 (t, J = 7.38 Hz, 1H, Ph-H), 7.225 (d, J = 7.8 Hz, 2H, Ph-H), 7.124 (dd, J = 7.56, 5.58 Hz, 2H, Ph-H), 5.309 (s, 2H, -OCH2), 2.390 (s, 3H, -CH3). 13C NMR (150 MHz, CDCl3) δ ppm: 163.2 (thiazole-C), 156.3 (Ph-C), (benzothiazole-C), 138.0 (Ph-C), 136.1 (Ph-C), 133.0 (benzothiazole-C), 131.7 (Ph-C), 129.3 (Ph-C), 127.9 (Ph-C), 125.9 (Ph-C), 124.5 (Ph-C), 122.7 (Ph-C), 121.3 (Ph-C), 121.3 (Ph-C), 113.0 (Ph-C), 70.9 (-OCH2-), 21.2 (-CH3). Anal. Calcd for C21H17NOS: C, 76.10%; H, 5.17%; N, 4.23%; Found: C, 76.08%; H, 5.16%; N, 4.22%.
2-(2-(benzyloxy)phenyl)benzo[d]thiazole (A7 ) Gray solid; Yield/%: 70%; Mp/°C: 89.7∼91.7; ESI-MS [M + H]+: 318.4; 1H NMR (600 MHz, CDCl3) δ ppm: 8.557 (dd, J = 7.98, 1.50 Hz, 1H, Ph-H), 8.089 (d, J = 8.22 Hz, 1H, Ph-H), 7.879 (d, J = 7.98 Hz, 1H, Ph-H), 7.546 (d, J = 7.32 Hz, 2H, Ph-H), 7.481 (t, J = 8.04 Hz, 1H, Ph-H), 7.342–7.435 (m, 5H, Ph-H), 7.102–7.151 (m, 2H, Ph-H), 5.352(s, 2H, -OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 163.3 (thiazole-C), 156.3 (benzothiazole-C), 136.0 (Ph-C), 131.9 (Ph-C), (benzothiazole-C), 129.9 (Ph-C), 128.6 (Ph-C), 128.3 (Ph-C), 127.8 (Ph-C), 126.0 (Ph-C), 124.7 (Ph-C), 122.6 (Ph-C), 121.5 (Ph-C), 121.3 (Ph-C), 113.0 (Ph-C), 71.0 (-OCH2-). Anal. Calcd for C20H15NOS: C, 75.68%; H, 4.76%; N, 4.41%; Found: C, 75.70%; H, 4.77%; N, 4.42%.
4-((2-(benzo[d]thiazol-2-yl)phenoxy)methyl)benzonitrile (A8 ) Gray solid; Yield/%: 66%; Mp/°C: 131.8∼133.8; ESI-MS [M + H]+: 343.1; 1H NMR (600 MHz, CDCl3) δ ppm: 8.546 (d, J = 7.8 Hz, 1H, Ph-H), 8.098 (d, J = 8.16 Hz, 1H, Ph-H), 7.894 (d, J = 7.92 Hz, 1H, Ph-H), 7.717 (d, J = 8.1Hz, 2H, Ph-H), 7.660 (d, J = 8.04 Hz, 2H, Ph-H), 7.501 (t, J = 7.74 Hz, 1H, Ph-H), 7.431 (t, J = 8.1 Hz,1H, Ph-H), 7.381 (t, J = 7.68Hz, 1H, Ph-H), 7.175 (t, J = 7.56 Hz, 1H, Ph-H), 7.041 (d, J = 8.34 Hz, 1H, Ph-H), 5.380 (s, 2H, -OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 155.7 (thiazole-C), 141.4 (benzothiazole-C), 132.5 (benzothiazole-C), 131.9 (Ph-C), 130.2 (Ph-C), 128.1 (Ph-C), 126.2 (Ph-C), 124.9 (Ph-C), 122.8 (Ph-C), 122.0 (Ph-C), 121.3 (Ph-C), 118.5 (-CN), 112.8 (Ph-C), 112.2 (Ph-C), 70.1 (-OCH2-). Anal. Calcd for C21H14N2OS: C, 73.66%; H, 4.12%; N, 8.18%; Found: C, 73.64%; H, 4.11%; N, 8.17%.
6-fluoro-N-phenethylbenzo[d]thiazol-2-amine (B1 ) White solid; Yield/%: 86%; Mp/°C: 132.4∼134.6; ESI-MS [M + H]+: 273.1; 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.85 (s, 1H, -NH), 8.07–8.04 (m, 1H, Ph-H), 7.85–7.79 (m, 3H, Ph-H), 7.60 (dd, J = 9.9, 2.5 Hz, 1H, Ph-H), 7.25–7.13 (m, 3H, Ph-H), 3.89 (s, 2H, -CH2), 3.87 (s, 2H, -CH2). 13C NMR (101 MHz, DMSO-d6) δ ppm: 165.6 (thiazole-C), 163.0 (Ph-C), 161.9 (Ph-C), 160.6 (Ph-C), 153.2 (Ph-C), 148.9 (benzothiazole-C), 123.4 (C, d, JC−C−C−F = 10.10 Hz), 122.9 (Ph-C), 112.2 (Ph-C), 111.9 (Ph-C), 111.6 (C, d, JC−C−C−C−F = 4.04 Hz), 106.8 (C, d, JC−C−F = 24.24 Hz), 56.2 (-CH2CH2-), 56.1 (-CH2CH2-). Anal. Calcd for C15H13FN2S: C, 66.15%; H, 4.81%; N, 10.29%; Found: C, 66.16%; H, 4.82%; N, 10.30%.
N-(2,6-dichlorobenzyl)-6-fluorobenzo[d]thiazol-2-amine (B2 ) Gray solid; Yield/%: 77%; Mp/°C: 156.8∼158.2; ESI-MS [M + H]+: 327.0; 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.57 (d, J = 4.5 Hz, 1H, Ph-H), 7.70 (dd, J = 8.6, 5.6 Hz, 1H, Ph-H), 7.55 (d, J = 8.1 Hz, 2H, Ph-H), 7.43 (dd, J = 8.7, 7.5 Hz, 1H, Ph-H), 7.28 (dd, J = 10.4, 2.5 Hz, 1H, Ph-H), 6.99–6.85 (m, 1H, Ph-H), 4.83 (s, 2H, -CH2). 13C NMR (101 MHz, DMSO-d6) δ ppm: 168.1 (thiazole-C), 163.0 (Ph-C), 160.6 (benzothiazole-C), 136.2 (Ph-C), 132.9 (Ph-C), 131.2 (Ph-C), 129.1 (Ph-C), 126.0 (benzothiazole-C), 122.5 (C, d, JC−C−C−F = 10.1 Hz), 109.1(C, d, JC−C−F = 24.24 Hz), 105.1(C, d, JC−C−F = 24.25 Hz), 44.1 (-CH2-). Anal. Calcd for C14H9Cl2FN2S: C, 51.39%; H, 2.77%; N, 8.56%; Found: C, 51.37%; H, 2.76%; N, 8.55%.
N-(3,4-dimethoxybenzyl)-6-fluorobenzo[d]thiazol-2-amine (B3 ) Gray solid; Yield/%: 79%; Mp/°C: 135.5∼137.4; ESI-MS [M + H]+: 319.1; 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.56 (s, 1H, -NH), 7.43 (dd, J = 8.3, 5.5 Hz, 1H, Ph-H), 7.11 (s, 1H, Ph-H), 6.99–6.75 (m, 4H, Ph-H), 5.08 (s, 2H, -CH2). 3.73 (d, J = 5.1 Hz, 6H, -OCH3). 13C NMR (101 MHz, DMSO-d6) δ ppm: 163.0 (thiazole-C), 160.6 (Ph-C), 160.0 (Ph-C), 149.2 (benzothiazole-C), 148.5 (Ph-C), 141.9 (Ph-C), 141.8 (Ph-C), 129.2 (benzothiazole-C), 123.1 (C, d, JC−C−C−F = 9.09 Hz), 119.8 (Ph-C), 117.9 (Ph-C), 112.1 (C, d, JC−C−F = 18.18 Hz), 108.1 (C, d, JC−C−F = 23.23 Hz), 98.6 (Ph-C), 98.3 (Ph-C), 55.9 (-OCH3), 45.1 (-CH2-). Anal. Calcd for C16H15FN2O2S: C, 60.36%; H, 4.75%; N, 8.80%; Found: C, 60.38%; H, 4.76%; N, 8.81%.
6-fluoro-N-(4-nitrobenzyl)benzo[d]thiazol-2-amine (B4 ) White solid; Yield/%: 65%; Mp/°C: 142.5∼144.7; ESI-MS [M + H]+: 304.1; 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.86 (t, J = 5.9 Hz, 1H, -NH), 8.27–8.21 (m, 2H, Ph-H), 7.70 (dd, J = 8.6, 5.6 Hz, 1H, Ph-H), 7.66–7.59 (m, 2H, Ph-H), 7.20 (dd, J = 10.5, 2.5 Hz, 1H, Ph-H), 6.91 (td, J = 9.3, 2.6 Hz, 1H, Ph-H), 4.76 (d, J = 5.9 Hz, 2H, -CH2). 13C NMR (101 MHz, DMSO-d6) δ ppm: 168.8 (thiazole-C), 153.9 (C, d, JC−C−C−F = 12.12 Hz), 147.2 (C, d, JC−C−F = 40.40 Hz), 128.6 (Ph-C), 127.5 (Ph-C), 126.4 (benzothiazole-C), 124.1 (Ph-C), 122.4 (C, d, JC−C−F = 10.10 Hz), 109.1 (Ph-C), 105.5 (Ph-C), 46.9 (-CH2-). Anal. Calcd for C14H10FN3O2S: C, 55.44%; H, 3.32%; N, 13.85%; Found: C, 55.47%; H, 3.33%; N, 13.86%.
6-chloro-N-(3-fluorobenzyl)benzo[d]thiazol-2-amine (B5 ) White solid; Yield/%: 45%; Mp/°C: 145.6∼147.6; ESI-MS [M + H]+: 293.5; 1H NMR (600 MHz, CDCl3) δ ppm:7.545 (d, J = 2.1 Hz, 1H, Ph-H),7.429 (d, J = 8.64 Hz, 1H, Ph-H), 7.103–7.246 (m, 5H, Ph-H), 5.149 (s, 1H, -NH), 4.646 (s, 2H, -OCH2). 13C NMR (150 MHz, CDCl3) δ ppm: 130.4 (benzothiazole-C), 130.4 (Ph-C), 127.0 (Ph-C), 126.5 (Ph-C), 123.1 (Ph-C), 123.1 (Ph-C), 120.5 (Ph-C), 119.8 (Ph-C), 114.9 (Ph-C), 114.8 (Ph-C), 114.6 (Ph-C), 114.4 (Ph-C), 48.6 (-CH2-). Anal. Calcd for C14H10ClFN2S: C, 57.44%; H, 3.44%; N, 9.57%; Found: C, 57.48%; H, 3.45%; N, 9.58%.
6-chloro-N-(3,5-dimethoxybenzyl)benzo[d]thiazol-2-amine (B6 ) Pale yellow solid; Yield/%: 58%; Mp/°C: 101.3∼103.3; ESI-MS [M + H]+: 335.1; 1H NMR (600 MHz, CDCl3) δ ppm: 7.539 (d, J = 1.98 Hz, 1H, Ph-H), 7.427 (d, J = 8.58 Hz, 1H, Ph-H), 7.236 (s, 1H, Ph-H), 6.342–6.528 (m, 3H, Ph-H), 5.083 (s, 1H, -NH), 4.557(s, 2H, -CH2), 3.746 (s, 6H, -OCH3). 13C NMR (150 MHz, CDCl3) δ ppm: 167.5 (thiazole-C), 161.3 (Ph-C),151.0 (benzothiazole-C), 139.6 (Ph-C), 131.8 (benzothiazole-C), 126.5 (Ph-C), 121.5 (Ph-C), 120.6 (Ph-C), 119.7 (Ph-C), 110.7 (Ph-C), 107.0 (Ph-C), 107.0 (Ph-C), 105.7 (Ph-C), 99.8 (Ph-C), 99.1 (Ph-C), 55.5 (-CH3), 49.5 (-CH2-). Anal. Calcd for C16H15ClN2O2S: C, 57.40%; H, 4.52%; N, 8.37%; Found: C, 57.36%; H, 4.51%; N, 8.36%.
6-chloro-N-(4-nitrobenzyl)benzo[d]thiazol-2-amine (B7 ) Pale yellow solid; Yield/%: 31%; Mp/°C: 148.4∼150.8; ESI-MS [M + H]+: 320.4; 1H NMR (600 MHz, CDCl3) δ ppm: 8.412 (d, J = 8.4 Hz, 1H, Ph-H), 8.216 (d, J = 8.4 Hz, 2H, Ph-H), 8.199 (s, 1H, Ph-H), 8.145 (d, J = 8.4 Hz, 1H, Ph-H), 7.451 (d, J = 8.4 Hz, 2H, Ph-H), 4.850 (s, 2H, -CH2), 3.077 (s, 1H, -NH). 13C NMR (150 MHz, CDCl3) δ ppm: 167.5 (thiazole-C), 158.7 (benzothiazole-C),151.1 (Ph-C), 129.6 (Ph-C), 129.5 (benzothiazole-C), 126.6 (Ph-C), 121.6 (Ph-C), 115.8 (Ph-C), 110.5 (Ph-C), 48.7 (-CH2-). Anal. Calcd for C14H10ClN3O2S: C, 52.59%; H, 3.15%; N, 13.14%; Found: C, 52.61%; H, 3.14%; N, 13.13%.
N-benzyl-6-chlorobenzo[d]thiazol-2-amine (B8 ) Pale yellow solid; Yield/%: 50%; Mp/°C: 123.5∼125.5; ESI-MS [M + H]+: 275.1; 1H NMR (600 MHz, CDCl3) δ ppm: 7.540 (d, J = 2.04 Hz, 1H, Ph-H), 7.357–7.394 (m, 3H, Ph-H), 7.305–7.332 (m, 3H, Ph-H), 7.243 (d, J = 2.04 Hz, 1H, Ph-H), 5.160 (s, 1H, -NH), 4.631(s, 2H, -CH2). 13C NMR (125 MHz, DMSO-d6) δ ppm: 166.9 (thiazole-C), 151.2 (benzothiazole-C), 138.5 (Ph-C), 131.9 (benzothiazole-C), 128.6 (Ph-C), 128.3 (Ph-C), 127.3 (Ph-C), 127.1 (Ph-C), 126.8 (Ph-C), 125.7 (Ph-C), 124.7 (Ph-C), 120.5 (Ph-C), 118.9 (Ph-C), 47.2 (-CH2-). Anal. Calcd for C14H11ClN2S: C, 61.20%; H, 4.04%; N, 10.20%; Found: C, 61.17%; H, 4.03%; N, 10.19%.
N-(6-fluorobenzo[d]thiazol-2-yl)benzamide (C1 ) Gray solid; Yield/%: 45%; Mp/°C: >300; ESI-MS [M + H]+: 273.1; 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.99 (s, 1H, -CONH), 8.21–8.11 (m, 2H, Ph-H), 8.06 (dd, J = 8.7, 5.5 Hz, 1H, Ph-H), 7.68 (t, J = 7.4 Hz, 1H, Ph-H), 7.65–7.53 (m, 3H, Ph-H), 7.23 (td, J = 9.1, 2.4 Hz, 1H, Ph-H). 13C NMR (101 MHz, DMSO-d6) δ 166.4 (thiazole-C), 163.0 (Ph-C), 161.6 (Ph-C), 160.6 (Ph-C), 133.4 (Ph-C), 132.1 (Ph-C), 129.1 (Ph-C), 128.8 (Ph-C), 127.8 (benzothiazole-C), 123.5 (C, d, JC−C−C−F = 10.10 Hz), 112.2 (C, d, JC−C−F = 24.24 Hz), 107.0 (C, d, JC−C−F = 24.24 Hz). Anal. Calcd for C14H9FN2OS: C, 61.75%; H, 3.33%; N, 10.29%; Found: C, 61.73%; H, 3.32%; N, 10.28%.
2,6-dichloro-N-(6-fluorobenzo[d]thiazol-2-yl) benzamide (C2 ) White solid; Yield/%: 51%; Mp/°C: >300; ESI-MS [M + H]+: 341.0; 1H NMR (400 MHz, DMSO-d6) δ ppm: 13.32 (s, 1H, -CONH), 8.09 (dd, J = 8.8, 5.5 Hz, 1H, Ph-H), 7.73–7.48 (m, 4H, Ph-H), 7.26 (td, J = 9.1, 2.5 Hz, 1H, Ph-H). 13C NMR (101 MHz, DMSO-d6) δ ppm: 163.8 (thiazole-C), 163.1 (Ph-C), 160.7 (Ph-C), 160.1 (Ph-C), 150.0 (C, d, JC−C−C−F = 12.12 Hz), 134.6 (Ph-C), 132.8 (Ph-C), 131.6 (Ph-C), 128.8 (benzothiazole-C), 127.8 (Ph-C), 123.7 (C, d, JC−C−C−F = 10.10 Hz), 112.7 (C, d, JC−C−F = 24.24 Hz), 107.6 (C, d, JC−C−F = 24.24 Hz). Anal. Calcd for C14H7Cl2FN2OS: C, 49.29%; H, 2.07%; N, 8.21%; Found: C, 49.31%; H, 2.08%; N, 8.22%.
N-(6-fluorobenzo[d]thiazol-2-yl)-3,4-dimethoxybenzamide (C3 ) White solid; Yield/%: 46%; Mp/°C: >300; ESI-MS [M + H]+: 333.1; 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.86 (s, 1H, -CONH), 8.05 (dd, J = 8.7, 5.5 Hz, 1H, Ph-H), 7.93–7.74 (m, 2H, Ph-H), 7.60 (dd, J = 10.0, 2.2 Hz, 1H, Ph-H), 7.22 (td, J = 9.1, 2.4 Hz, 1H, Ph-H), 7.14 (d, J = 8.5 Hz, 1H, Ph-H), 3.88 (d, J = 7.1 Hz, 6H, -OCH3). 13C NMR (101 MHz, DMSO-d6) δ ppm: 165.6 (thiazole-C), 163.0 (Ph-C), 161.9 (Ph-C), 160.6 (Ph-C), 153.2 (Ph-C), 150.1 (benzothiazole-C), 148.8 (Ph-C), 127.8 (Ph-C), 123.7 (C, d, JC−C−C−F = 55.55 Hz), 122.8 (Ph-C), 111.8 (C, d, JC−C−F = 32.32 Hz), 111.6, 106.9 (C, d, JC−C−F = 25.25 Hz), 56.2 (-OCH3). Anal. Calcd for C16H13FN2O3S: C, 57.82%; H, 3.94%; N, 8.43%; Found: C, 57.79%; H, 3.93%; N, 8.42%.
N-(6-fluorobenzo[d]thiazol-2-yl)-4-nitrobenzamide (C4 ) White solid; Yield/%: 60%; Mp/°C:187.7∼189.4; ESI-MS [M + H]+: 319.1; 1H NMR (400 MHz, CF3COOD) δ ppm: δ 8.61 (dd, J = 63.9, 8.5 Hz, 4H, Ph-H), 8.21 (dd, J = 9.2, 4.4 Hz, 1H, Ph-H), 7.89 (d, J = 7.7 Hz, 1H, Ph-H), 7.64 (t, J = 8.9 Hz, 1H, Ph-H). 13C NMR (101 MHz, CF3COOD) δ ppm: 165.44 (thiazole-C), 151.2 (benzothiazole-C), 136.0 (C, d, JC−C−C−F = 13.13 Hz), 134.8 (Ph-C), 129.8 (benzothiazole-C), 124.4 (Ph-C), 121.1 (Ph-C), 118.6 (Ph-C), 116.7 (C, d, JC−C−F = 25.25 Hz), 115.8 (Ph-C), 113.0 (Ph-C), 110.18 (Ph-C), 103.3 (C, d, JC−C−F = 28.28 Hz). Anal. Calcd for C14H8FN3O3S: C, 53.00%; H, 2.54%; N, 13.24%; Found: C, 53.03%; H, 2.55%; N, 13.22%.
N-(6-chlorobenzo[d]thiazol-2-yl)-4-methoxybenzamide (C5 ) Gray solid; Yield/%: 70%; Mp/°C: >300, ESI-MS [M + H]+: 319.1; 1H NMR (600 MHz, CDCl3) δ ppm: 10.081 (s, 1H, -NH), 7.947 (d, J = 8.3 Hz, 2H, Ph-H), 7.813 (s, 1H, Ph-H), 7.376 (d, J = 8.6 Hz, 1H, Ph-H), 7.291 (d, J = 8.6 Hz, 1H, Ph-H), 3.862 (s, 3H, -OCH3). 13C NMR (150 MHz, DMSO-d6) δ ppm: 166.1 (thiazole-C), 163.3 (-C=O), 160.7 (Ph-C), 147.8 (benzothiazole-C), 133.7 (benzothiazole-C), 130.9 (Ph-C), 127.9 (Ph-C), 126.8 (Ph-C), 124.4 (Ph-C), 121.8 (Ph-C), 121.7 (Ph-C), 114.4 (Ph-C), 56.0 (-OCH3). Anal. Calcd for C15H11ClN2O2S: C, 56.52%; H, 3.48%; N, 8.79%; Found: C, 56.59%; H, 3.47%; N, 8.78%.
N-(6-chlorobenzo[d]thiazol-2-yl)benzamide (C6 ) Gray solid; Yield/%: 82%; Mp/°C: >300; ESI-MS [M + H]+: 289.1; 1H NMR (600 MHz, CDCl3) δ ppm: 11.011 (s, 1H, -NH), 7.985 (d, J = 7.86 Hz, 2H, Ph-H), 7.819 (s, 1H, Ph-H), 7.610 (t, J = 7.1 Hz, 2H, Ph-H), 7.481 (d, J = 7.5 Hz, 2H, Ph-H), 7.273 (s, 1H, Ph-H). 13C NMR (150 MHz, DMSO-d6) δ ppm: 166.9 (thiazole-C), 160.6 (-C=O), 147.7 (benzothiazole-C), 133.7 (Ph-C), 133.3 (benzothiazole-C), 132.5 (Ph-C), 129.1 (Ph-C), 128.7 (Ph-C), 128.0 (Ph-C), 126.9 (Ph-C), 121.9 (Ph-C), 121.7 (Ph-C). Anal. Calcd for C14H9ClN2OS: C, 58.24%; H, 3.14%; N, 9.70%; Found: C, 58.20%; H, 3.13%; N, 9.71%.
N-(6-chlorobenzo[d]thiazol-2-yl)-2-fluorobenzamide (C7 ) White solid; Yield/%: 77%; Mp/°C: >300; ESI-MS [M + H]+: 307.0; 1H NMR (600 MHz, CDCl3) δ ppm: 11.755 (s, 1H, -NH), 9.562 (s, 1H, Ph-H), 9.444 (d, J = 8.58 Hz, 1H, Ph-H), 9.350–9.385 (m, 1H, Ph-H), 9.105–9.155 (m, 2H, Ph-H), 9.006 (s, 1H, Ph-H), 8.971 (s, 1H, Ph-H). 13C NMR (1500 MHz, DMSO-d6) δ ppm: 166.0 (thiazole-C), 165.9 (-C=O), 164.2(benzothiazole-C), 133.4(benzothiazole-C), 131.7 (Ph-C), 131.6 (Ph-C), 128.2 (Ph-C), 127.0 (Ph-C), 122.0 (Ph-C), 121.8 (Ph-C), 116.2 (Ph-C), 116.1 (Ph-C). Anal. Calcd for C14H8ClFN2OS: C, 54.82%; H, 2.63%; N, 9.13%; Found: C, 54.79%; H, 2.62%; N, 9.14%.
6-chloro-N,N-bis(3,5-dimethoxybenzyl)benzo[d]thiazol-2-amine (D1 ) White solid; Yield/%: 20%; Mp/°C: 83.4∼85.3; ESI-MS [M + H]+: 485.1; 1H NMR (600 MHz, CDCl3) δ ppm: 7.533 (d, J = 2.04 Hz, 1H, Ph-H), 7.311 (d, J = 2.04 Hz, 1H, Ph-H), 6.331–6.549 (m, 7H, Ph-H), 4.663 (s, 4H, -CH2), 3.743 (s, 12H, -OCH3). 13C NMR (150 MHz, CDCl3) δ ppm: 169.2 (thiazole-C), 161.2 (Ph-C), 151.6 (benzothiazole-C), 138.6 (Ph-C), 132.3 (benzothiazole-C), 126.5 (Ph-C), 123.9 (Ph-C), 122.2 (Ph-C), 120.4 (Ph-C), 119.7 (Ph-C), 100.0 (Ph-C), 99.6 (Ph-C), 55.4 (-CH2-, -OCH3). Anal. Calcd for C25H25ClN2O4S: C, 61.91%; H, 5.20%; N, 5.78%; Found: C, 61.93%; H, 5.21%; N, 5.79%.
N,N-dibenzyl-6-chlorobenzo[d]thiazol-2-amine (D2 ) Gray solid; Yield/%: 21%; Mp/°C: 134.4∼136.4; ESI-MS [M + H]+: 365.1; 1H NMR (600 MHz, CDCl3) δ ppm: 7.321–7.360 (m, 10H, Ph-H), 7.282 (d, J = 2.34 Hz, 1H, Ph-H), 7.059 (dd, J = 8.7, 2.34 Hz, 1H, Ph-H), 6.962 (d, J = 8.52 Hz, 1H, Ph-H), 4.484 (s, 2H, -CH2), 4.178 (s, 2H, -CH2). 13C NMR (150 MHz, DMSO-d6) δ ppm: 136.1 (benzothiazole-C), 134.1 (Ph-C), 133.0 (Ph-C), 129.0 (Ph-C), 128.9 (Ph-C), 128.6 (Ph-C), 128.5 (Ph-C), 127.6 (Ph-C), 127.4 (Ph-C), 126.4 (Ph-C), 56.6 (-CH2-). Anal. Calcd for C21H17ClN2S: C, 69.13%; H, 4.70%; N, 7.68%; Found: C, 69.16%; H, 4.71%; N, 7.69%.
2-(2-((2-nitrobenzyl)oxy)phenyl)benzo[d]thiazole (
2-(3-(2-(benzo[d]thiazol-2-yl)phenoxy)propyl)isoindoline-1,3-dione (
2-(2-((4-nitrobenzyl)oxy)phenyl)benzo[d]thiazole (
2-(2-((3-chlorobenzyl)oxy)phenyl)benzo[d]thiazol (
2-(2-((4-methylbenzyl)oxy)phenyl)benzo[d]thiazole (
2-(2-(benzyloxy)phenyl)benzo[d]thiazole (
4-((2-(benzo[d]thiazol-2-yl)phenoxy)methyl)benzonitrile (
6-fluoro-N-phenethylbenzo[d]thiazol-2-amine (
N-(2,6-dichlorobenzyl)-6-fluorobenzo[d]thiazol-2-amine (
N-(3,4-dimethoxybenzyl)-6-fluorobenzo[d]thiazol-2-amine (
6-fluoro-N-(4-nitrobenzyl)benzo[d]thiazol-2-amine (
6-chloro-N-(3-fluorobenzyl)benzo[d]thiazol-2-amine (
6-chloro-N-(3,5-dimethoxybenzyl)benzo[d]thiazol-2-amine (
6-chloro-N-(4-nitrobenzyl)benzo[d]thiazol-2-amine (
N-benzyl-6-chlorobenzo[d]thiazol-2-amine (
N-(6-fluorobenzo[d]thiazol-2-yl)benzamide (
2,6-dichloro-N-(6-fluorobenzo[d]thiazol-2-yl) benzamide (
N-(6-fluorobenzo[d]thiazol-2-yl)-3,4-dimethoxybenzamide (
N-(6-fluorobenzo[d]thiazol-2-yl)-4-nitrobenzamide (
N-(6-chlorobenzo[d]thiazol-2-yl)-4-methoxybenzamide (
N-(6-chlorobenzo[d]thiazol-2-yl)benzamide (
N-(6-chlorobenzo[d]thiazol-2-yl)-2-fluorobenzamide (
6-chloro-N,N-bis(3,5-dimethoxybenzyl)benzo[d]thiazol-2-amine (
N,N-dibenzyl-6-chlorobenzo[d]thiazol-2-amine (
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Buff solid (yield 66.6%), m.p. 346–347 °C; IR (KBr, ν cm−1): 3463, 3266 (NH2, NH), 3057 (Ar-CH); 1H NMR (400 MHz, DMSO-d6): δ 7.26 (t, J = 7.6 Hz, 1H, benzothiazole-CH), 7.39–7.47 (m, 2H, benzothiazol-H), 7.55 (t, J = 7.6 Hz, 1H, benzothiazole-CH), 7.69 (d, J = 8.0 Hz, 1H, benzothiazole-CH), 7.90 (d, J = 7.8 Hz, 1H, benzothiazole-CH), 8.06 (d, J = 8.0 Hz, 1H, benzothiazole-CH), 8.13 (d, J = 8.0 Hz, 1H, benzothiazole-CH), 8.78 (s, 1H, pyrimidine-CH), 11.8 (br, 1H, NH); anal. calcd for C18H12N6S2 (376.46): calc C% 57.43; H% 3.21; N% 22.32; S% 17.04; found C% 57.47; H% 3.17; N% 22.38; S% 17.10.
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Benzothiazole is a heterocyclic organic compound used in various laboratory applications. It is a fused ring system composed of a benzene ring and a thiazole ring. Benzothiazole serves as a core structural element in the development and study of diverse chemical compounds and materials.
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More about "Benzothiazole"
Benzothiazole is a heterocyclic aromatic compound composed of a benzene ring fused to a thiazole ring.
This versatile molecule finds applications in the synthesis of various pharmaceuticals, dyes, and industrial chemicals.
Derivatives of benzothiazole have been reported to exhibit a wide range of biological activities, including antimicrobial, antifungal, anti-inflammatory, and antitumor properties.
Researchers utilize these compounds in diverse fields, from medical treatments to materials science.
Optimizing the research process for benzothiazole can be facilitated by powerful AI-driven tools like PubCompare.ai.
This platform helps identify the best protocols and products from the literature, preprints, and patents, enhancing reproducibility and streamlining the research workflow.
By leveraging PubCompare.ai's AI-driven comparisons, scientists can locate the most relevant and effective protocols, improving the efficiency and success of their benzothiazole-related studies.
In addition to benzothiazole, other compounds like DMEM (Dulbecco's Modified Eagle Medium), acetonitrile, ascorbic acid, formic acid, FBS (Fetal Bovine Serum), DMSO (Dimethyl Sulfoxide), stearic acid, and EDTA (Ethylenediaminetetraacetic acid) are commonly used in biochemical and materials research.
The integration of Prism 9, a powerful data analysis and visualization software, can further enhance the understainding and interpretation of benzothiazole-related findings.
By leveraging the insights and tools available, researchers can optimize their benzothiazole studies, leading to advancements in pharmaceutical development, materials engineering, and other relevant fields.
The combination of benzothiazole's versatility and the power of AI-driven platforms like PubCompare.ai can streamline the research process and drive innovation.
This versatile molecule finds applications in the synthesis of various pharmaceuticals, dyes, and industrial chemicals.
Derivatives of benzothiazole have been reported to exhibit a wide range of biological activities, including antimicrobial, antifungal, anti-inflammatory, and antitumor properties.
Researchers utilize these compounds in diverse fields, from medical treatments to materials science.
Optimizing the research process for benzothiazole can be facilitated by powerful AI-driven tools like PubCompare.ai.
This platform helps identify the best protocols and products from the literature, preprints, and patents, enhancing reproducibility and streamlining the research workflow.
By leveraging PubCompare.ai's AI-driven comparisons, scientists can locate the most relevant and effective protocols, improving the efficiency and success of their benzothiazole-related studies.
In addition to benzothiazole, other compounds like DMEM (Dulbecco's Modified Eagle Medium), acetonitrile, ascorbic acid, formic acid, FBS (Fetal Bovine Serum), DMSO (Dimethyl Sulfoxide), stearic acid, and EDTA (Ethylenediaminetetraacetic acid) are commonly used in biochemical and materials research.
The integration of Prism 9, a powerful data analysis and visualization software, can further enhance the understainding and interpretation of benzothiazole-related findings.
By leveraging the insights and tools available, researchers can optimize their benzothiazole studies, leading to advancements in pharmaceutical development, materials engineering, and other relevant fields.
The combination of benzothiazole's versatility and the power of AI-driven platforms like PubCompare.ai can streamline the research process and drive innovation.