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> Chemicals & Drugs > Organic Chemical > Quinoline

Quinoline

Quinoline is a heterocyclic organic compound consisting of a benzene ring fused to a pyridine ring.
It is widely used in the synthesis of pharmaceuticals, dyes, and other chemical products.
Quinoline derivatives have a diverse range of biological activities, including antimalarial, antibacterial, antifungal, and anticancer properties.
Researchers in the field of quinoline chemistry often leverage PubCompare.ai's AI-driven platform to optimize their reproducible research protocols, easily locate relevant protocols from literature, pre-prints, and patents, and identify the best protocols and products through AI-driven comparisons.
PubCompare.ai's precise and effecient tools can help streamline quinoline research and accelerate the development of new therapeutic agents.

Most cited protocols related to «Quinoline»

1
Induction of Mitosis Arrest and Apoptosis
Cited 28 times
The inhibition of mitosis and the induction of apoptosis in KG1a and MV4–11 cells were induced respectively by exposure to camptothecin (Sigma-Aldrich, Saint-Quentin Fallavier, France), a cytotoxic quinoline alkaloid which inhibits the DNA enzyme topoisomerase I [10] (link), [11] (link) and by AZD8055 (AstraZeneca Cancer & Infection Research Area, Alderley Park, UK) [12] (link), a selective inhibitor of mTOR kinase, respectively. Cells were seeded at 2×105 cells/mL (5% CO2 incubator at 37°C). KG1a cells were cultured for 6h with camptothecin at a final concentration of 1 µM and MV4–11 cells were cultured for 24 h with AZD8055 at a final concentration of 10 nM and 100 nM. The stock solutions were diluted to ensure a final concentration of <0.03% for DMSO (Sigma-Aldrich). Control cultures were treated with an equivalent volume of DMSO in MEM alpha medium which did not induce apoptosis.
Quiescence was induced in KG1a cells by contact with BM MSCs [13] (link). Adherent culture-amplified MSCs were used at passage 2 (P2). KG1a cells were co-cultured on P2-MSCs for 72 h (37°C in 95% humidified air and 5% CO2) at a starting concentration of 1.5×104/cm2.
The accumulation of KG1a cells in the M phase was induced by exposure to colcemid (KaryoMax Colcemid, Life Technologies), used for arresting the dividing cell at metaphase of mitosis. Cells were cultured 30 min and 1 h with colcemid at a final concentration of 0.1 µg/mL.
Lymphocytes stimulation was induced by exposure to phytohemagglutinin (PHA) (Remel™, Oxoid™, Haarlem, The Netherlands), which is used to stimulate mitotic division of lymphocytes. Whole blood cells were cultured 72 h with PHA at a final concentration of 170 µg/mL according to the manufacturer’s recommandations.
All experiments were performed in triplicate.
Vignon C., Debeissat C., Georget M.T., Bouscary D., Gyan E., Rosset P, & Herault O. (2013). Flow Cytometric Quantification of All Phases of the Cell Cycle and Apoptosis in a Two-Color Fluorescence Plot. PLoS ONE, 8(7), e68425.
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Publication 2013
Apoptosis AZD8055 Blood Cells Camptothecin Cells Colcemide Division Phase, Cell Enzymes Infection Lymphocyte Lymphocyte Activation Malignant Neoplasms Metaphase Mitosis MTOR Inhibitors Phytohemagglutinins Plant Alkaloids Psychological Inhibition quinoline Sulfoxide, Dimethyl TOP1 protein, human
2
Ethanol-Induced Neurodegeneration in P7 Mice
Cited 12 times

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Publication 2013
Animals Apoptosis Birth BLOOD Body Weight Brain Caimans Caspase Inhibitors Decapitation Dehydrogenase, Alcohol Ethanol Females Food Inflammation Institutional Animal Care and Use Committees Males Mice, House Mice, Inbred C57BL Nerve Degeneration Normal Saline quinoline quinoline-val-asp(OMe)-CH2-OPH Saline Solution Serum Sterility, Reproductive Torso Tween 80
3
Tobacco Filler Nicotine Extraction and Analysis
Cited 11 times
Tobacco filler from individual cigarettes was removed from the paper wrapper, 5 mL of 2N NaOH was added to 1.0 grams of tobacco filler in a 60 mL amber vial, followed by extraction with 50 mL of an MTBE stock that contained quinoline as an internal standard. A 1 mL aliquot of the extract was placed in a 2 mL amber vial for GC/MS analysis. The sample preparation and nicotine analytical method have been previously described.13 Five replicates were analyzed for each variety.
Richter P., Steven P.R., Bravo R., Lisko J.G., Damian M., Gonzalez-Jimenez N., Gray N., Keong L.M., Kimbrell J.B., Kuklenyik P., Lawler T.S., Lee G.E., Mendez M., Perez J., Smith S., Tran H., Tyx R, & Watson C.H. (2016). Characterization of SPECTRUM Variable Nicotine Research Cigarettes. Tobacco regulatory science, 2(2), 94-105.
Publication 2016
Amber Gas Chromatography-Mass Spectrometry methyl tert-butyl ether Nicotine Quinolines Tobacco Products
4
Synthesis and Validation of LDN-193189
Cited 9 times
We purchased dorsomorphin (Compound C, 6-[4-(2-piperidin-1-yl-ethoxy)phenyl]-3-pyridin-4-yl-pyrazolo[1,5-a]pyrimidine) from EMD Biosciences. We synthesized LDN-193189 (4-[6-(4-piperazin-1-ylphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) as previously described6 (link), determined its purity (99.8%) by HPLC and confirmed its structure by 1H-NMR and high-resolution mass spectrometry. The vehicle was 2% (wt/vol) (2-hydroxypropyl)-β-cyclodextrin in PBS, pH 7.4. We purchased dexamethasone from Sigma. Recombinant human BMP4, platelet-derived growth factor-BB and TGF-β were obtained from R&D Systems. We produced adenoviruses expressing GFP and Cre and quantified them by the plaque-titer method.
Yu P.B., Deng D.Y., Lai C.S., Hong C.C., Cuny G.D., Bouxsein M.L., Hong D.W., McManus P.M., Katagiri T., Sachidanandan C., Kamiya N., Fukuda T., Mishina Y., Peterson R.T, & Bloch K.D. (2008). BMP type I receptor inhibition reduces heterotopic ossification. Nature medicine, 14(12), 1363-1369.
Publication 2008
1H NMR Adenoviruses Becaplermin Bone Morphogenetic Protein 4 Cyclodextrins Dental Plaque Dexamethasone dorsomorphin High-Performance Liquid Chromatographies Homo sapiens Hypromellose LDN 193189 Mass Spectrometry Piperazine Pyrimidines quinoline Transforming Growth Factor beta
5
Synthesis and Characterization of Arylquin Inhibitors
Cited 7 times
Nutlin-3a, an inhibitor of MDM2 that is reported to bind directly to MDM2, release, stabilize and activate p53 10 (link), was acquired from Cayman Chemical Company. Brefeldin A, N-benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone(zVAD-fmk) and other chemicals were purchased from Sigma Aldrich or Fisher Scientific or were synthesized according to literature procedures. The synthesis of Arylquin 1, which utilized 4-(N,N-dimethylamino)-2-aminobenzaldehyde in a Friedländer condensation with 2-fluorophenylacetontrile 15 , and other heterocyclic families is described in Supplementary Note. The condensation of 2-amino-4-(N,N-dimethylamino)benzaldehyde with 2-(2-fluorophenyl)acetyl chloride secured 7-(dimethylamino)-3-(2-fluorophenyl)quinolin-2(1H)-one, and treatment with Lawesson's reagent 16 provided 7-(dimethylamino)-3-(2-fluorophenyl)quinoline-2(1H)-thione. S-alkylation of this intermediate with (+)-biotinyl-iodoacetamidyl-3,6-dioxaoctanediamine led to biotinylated Arylquin 9 (Supplementary Note). Solvents were used from commercial vendors without further purification unless otherwise noted. Nuclear magnetic resonance spectra were determined on a Varian instrument (1H, 400MHz; 13C, 100Mz). High resolution electrospray ionization (ESI) mass spectra were recorded on a LTQ-Orbitrap Velos mass spectrometer (Thermo Fisher Scientific, Waltham, MA, USA). The FT resolution was set at 100,000 (at 400 m/z). Samples were introduced through direct infusion using a syringe pump with a flow rate of 5 µL/min. MALDI mass spectra were obtained on a Bruker Utraflexstreme time-of-flight mass spectrometer (Billerica, MA), using DHB (2,5-dihydroxybenzoic acid) matrix. Purity of compounds was established by combustion analyses by Atlantic Microlabs, Inc., Norcross, GA. Compounds were chromatographed on preparative layer Merck silica gel F254 unless otherwise indicated.
Burikhanov R., Sviripa V.M., Hebbar N., Zhang W., Layton W.J., Hamza A., Zhan C.G., Watt D.S., Liu C, & Rangnekar V.M. (2014). Arylquins Target Vimentin to Trigger Par-4 Secretion for Tumor Cell Apoptosis. Nature chemical biology, 10(11), 924-926.
Publication 2014
2,3-dihydroxybenzoic acid 2-aminobenzaldehyde acetyl chloride Alkylation Anabolism Arylquin 1 benzaldehyde benzyloxycarbonyl-valyl-alanyl-aspartic acid benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone Brefeldin A Caimans Ketones Lawesson's reagent Magnetic Resonance Imaging Mass Spectrometry MDM2 protein, human nutlin-3A quinoline Silica Gel Solvents Spectrometry, Mass, Electrospray Ionization Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Syringes Thiones

Most recents protocols related to «Quinoline»

1
Synthesis and Characterization of Quinoline-3-Carboxamide Derivative
Quinoline derivative (1) was prepared according to our previously reported experimental procedure (Scheme 1).19 (link) A mixture of commercial quinoline-3-carboxylic acid and freshly distilled thionyl chloride was warmed into reflux for 3 h, then cooled to room temperature and evaporated under vacuum to dryness to quantitatively obtain the corresponding chloride acids (1). This crude material was used without further purification. A mixture of this acyl chloride (1, 1.0 equiv.) and 4-aminoacetophenone (2, 1.0 equiv.) in toluene (10 mL) was stirred at room temperature for 2 h and then treated with a saturated NaHCO3 solution. The biphasic solution was vigorously stirred for 30 min, then decanted, and finally separated. The collected aqueous phase was extracted with EtOAc (2 × 10 mL). The combined organic layer was dried over Na2SO4 and evaporated. The solid was washed with icy water and crude material was crystallized from ethanol. Yield 90%, white solid; m.p. = 255–257 °C; IR (KBr, cm−1): 3327, 3068, 3001, 1985, 1918, 1844, 1676, 1650, 1597, 1268, 1109, 799; 1H NMR (400 MHz, DMSO-d6) δH (ppm): 2.55 (s, 3H), 7.71 (t, J = 8.0 Hz, 1H), 7.89 (t, J = 8.0 Hz, 1H), 7.99 (s, 4H), 8.12 (dd, J = 8.0, 12.3 Hz, 2H), 8.99 (s, 1H), 9.37 (s, 1H), 10.90 (bs, 1H); 13C NMR (100 MHz, DMSO-d6) δC (ppm): 26.4 (CH3), 119.5 (2 × CH), 126.3 (C), 127.3 (C), 127.5 (CH), 128.8 (CH), 129.2 (CH), 129.3 (2 × CH), 131.5 (CH), 132.2 (C), 136.2 (CH), 143.4 (C), 148.5 (C), 149.0 (CH), 164.5 (C), 196.5 (C).
Polo-Cuadrado E., Osorio E., Acosta-Quiroga K., Camargo-Ayala P.A., Brito I., Rodriguez J., Alderete J.B., Forero-Doria O., Blanco-Acuña E.F, & Gutiérrez M. (2024). Nonlinear optical and spectroscopic properties, thermal analysis, and hemolytic capacity evaluation of quinoline-1,3-benzodioxole chalcone. RSC Advances, 14(15), 10199-10208.
Publication 2024
2
Synthesis of 2-Aryl-quinoline-4-carboxylic Acid Methyl Ester
2-Aryl-quinoline-4-carboxylic acid (3, 10 mmol) was suspended in SOCl2 (12 mmol) at 0 °C. The mixture was refluxed for 2 h and cooled to 0 °C. Methanol (5 mL) was added to get the hydrochloride salt of the methyl ester derivative. Cold water (15 mL) was added to the mixture and its pH was adjusted to 7.0 with saturated with aqueous NaHCO3 solution. The precipitated solid was filtered, washed with cold water (2 × 10 mL), and dried under reduced pressure to get 2-(phenyl derivates)-quinoline-4-carboxylic acid methyl ester.
Hamedifar H., Mirfattahi M., Khalili Ghomi M., Azizian H., Iraji A., Noori M., Moazzam A., Dastyafteh N., Nokhbehzaim A., Mehrpour K., Javanshir S., Mojtabavi S., Faramarzi M.A., Larijani B., Hajimiri M.H, & Mahdavi M. (2024). Aryl-quinoline-4-carbonyl hydrazone bearing different 2-methoxyphenoxyacetamides as potent α-glucosidase inhibitors; molecular dynamics, kinetic and structure–activity relationship studies. Scientific Reports, 14, 388.
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Publication 2024
3
Hydrogenation of Quinoline Derivatives
Quinoline and its derivatives were
hydrogenated by the transfer hydrogen (TH) reaction, using water as
a green solvent. The experiments were conducted in a Teflon-capped
10 mL glass reaction tube placed in a reactor, which is capable of
running 10 parallel reactions simultaneously. The conditions were
as follows: quinoline (0.5 mmol, 59 μL), Pd@Fe3O4 catalyst (5 mg), and 10 mL of deionized water were added
into a reaction tube. Then, THDB (2 mmol, 179 mg) was added to the
suspension and stirred at 80 °C with a stirring speed of 250
rpm. The progress of the reaction was monitored by thin-layer chromatography
(TLC) and gas chromatography–mass spectrometry (GC-MS). After
completion of the reaction, the product was extracted with chloroform
(3 × 5 mL), combined with organic layers, dried with sodium sulfate,
and then filtered through a short column packed with silica gel. The
product was taken up for GC to measure the conversion and selectivity
and identified by its molecular ion peak (m/z) detected in GC-MS.
Alghamdi H.S., Ajeebi A.M., Aziz M.A., Alzahrani A.S, & Shaikh M.N. (2024). Facile Transfer Hydrogenation of N-Heteroarenes and Nitroarenes Using Magnetically Recoverable Pd@SPIONs Catalyst. ACS Omega, 9(10), 11377-11387.
Publication 2024
4
Synthesis of Quinoline-Thiazolidine Conjugates
Not available on PMC !

Example 9

[Figure (not displayed)]

DIPEA (0.205 mL, 1.18 mmol) was added to 8-methyl-6-morpholinoquinoline-4-carboxylic acid Intermediate 25 (160 mg, 0.59 mmol), (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (151 mg, 0.88 mmol) and HATU (223 mg, 0.59 mmol) in MeCN (5 mL) and EtOAc (5 mL) at 20° C. The resulting mixture was stirred at 20° C. for 3 h. The reaction mixture was concentrated and diluted with EtOAc (75 mL), and washed sequentially with sat NaHCO3 (20 mL), water (15 mL), and sat brine (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC, PrepMethod F, (gradient: 12-35%) to give the title compound (50 mg, 20%) as a red solid; HRMS (ESI) m/z [M+H]+ calcd for C21H24N5O3S: 426.1594 found: 426.1600; 1H NMR (400 MHz, DMSO-d6) δ 9.17 (t, 1H), 8.81 (d, 1H), 7.77 (s, 1H), 7.68-7.62 (m, 2H), 5.32 (dd, 1H), 4.90 (d, 1H), 4.71 (d, 1H), 4.42-4.25 (m, 2H), 3.79 (t, 4H), 3.46-3.32 (m, overlapping with solvent), 2.73 (s, 3H).

Example 91

[Figure (not displayed)]

A vial was charged with tert-butyl 6-(1,4-oxazepan-4-yl)quinoline-4-carboxylate Intermediate 189 (0.085 g, 0.25 mmol) and 90% TFA (aq, 0.5 mL) and the reaction mixture was heated at 50° C. for 3 h. The reaction mixture was concentrated, a mixture of heptane and DCM (3 mL, 2:1) was added to the residue and the mixture was concentrated. A mixture of MeCN/EtOAc (3 mL, 1:1) and DIPEA (0.261 mL, 1.50 mmol) was added to the residue followed by HATU (0.114 g, 0.30 mmol). The mixture was stirred for 1 min after which (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) was added. The mixture was stirred at rt for 4 h and then partitioned between EtOAc (4 mL) and 8% NaHCO3 (aq, 5 mL). The aqueous layer was extracted with EtOAc (2×1 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative SFC, PrepMethod SFC-A, followed by preparative HPLC, PrepMethod V, (gradient: 5-95%) to give the title compound (30 mg, 27%); HRMS (ESI) m/z [M+H]+ calcd for C21H24N5O3S: 426.1594 found: 426.1576; 1H NMR (600 MHz, DMSO-d6) δ 8.93 (t, 1H), 8.53 (d, 1H), 7.82 (d, 1H), 7.50-7.45 (m, 2H), 7.30 (d, 1H), 5.26 (dd, 1H), 4.84 (d, 1H), 4.66 (d, 1H), 4.30-4.18 (m, 2H), 3.76-3.66 (m, overlapping with solvent), 3.57-3.51 (m, overlapping with solvent), 3.38-3.29 (m, overlapping with solvent), 1.95-1.88 (m, 2H).

Example 92

[Figure (not displayed)]

The compound was synthesized and purified analogous to the procedure of Example 91 starting from tert-butyl (R)-6-(2-((methylsulfonyl)methyl)morpholino)quinoline-4-carboxylate Intermediate 193 (0.102 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) to give the title compound (26 mg, 20%); HRMS (ESI) m/z [M+H]+ calcd for C22H26N5O5S2: 504.1370 found: 504.1372; 1H NMR (600 MHz, DMSO-d6) δ 9.00 (m, 1H), 8.68 (d, 1H), 7.91 (d, 1H), 7.68 (d, 1H), 7.62 (dd, 1H), 7.40 (d, 1H), 5.31-5.27 (m, 1H), 4.86 (d, 1H), 4.67 (d, 1H), 4.31 (dd, 1H), 4.23 (dd, 1H), 4.10-3.99 (m, 2H), 3.88-3.81 (m, 1H), 3.75-3.65 (m, 2H), 3.53 (dd, overlapping with solvent), 3.37-3.27 (m, overlapping with solvent), 3.01 (s, 3H), 2.91-2.82 (m, 1H), 2.73-2.68 (m, 1H).

Example 93

[Figure (not displayed)]

The compound was synthesized and purified analogous to the procedure of Example 91 starting from tert-butyl (S)-6-(2-(methoxymethyl)morpholino)quinoline-4-carboxylate Intermediate 194 (76 mg, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) to give the title compound (0.026 g, 22%); HRMS (ESI) m/z [M+H]+ calcd for C22H26N5O4S: 456.1700 found: 456.1712; 1H NMR (600 MHz, DMSO-d6) δ 8.99 (t, 1H), 8.66 (d, 1H), 7.88 (d, 1H), 7.69 (d, 1H), 7.64 (dd, 1H), 7.38 (d, 1H), 5.29 (dd, 1H), 4.85 (d, 1H), 4.68 (d, 1H), 4.32-4.22 (m, 2H), 3.99-3.93 (m, 1H), 3.78-3.68 (m, 3H), 3.64 (td, 1H), 3.48-3.42 (m, overlapping with solvent), 3.35-3.31 (m, overlapping with solvent), 3.27 (s, 3H), 2.80 (td, 1H), 2.61-2.56 (m, overlapping with solvent).

Example 94

[Figure (not displayed)]

The compound was synthesized analogous to the procedure of Example 91 starting from tert-butyl (S)-6-(2-((methylsulfonyl)methyl)morpholino)quinoline-4-carboxylate Intermediate 198 (0.102 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol). The compound was purified by preparative SFC, PrepMethod SFC-A, followed by PrepMethod SFC-D, to give the title compound (0.023 g, 18%); HRMS (ESI) m/z [M+H]+ calcd for C22H26N5O5S2: 504.1370, found: 504.1364; 1H NMR (600 MHz, DMSO-d6) δ 9.00 (t, 1H), 8.68 (d, 1H), 7.91 (d, 1H), 7.71 (d, 1H), 7.62 (dd, 1H), 7.39 (d, 1H), 5.31-5.26 (m, 1H), 4.85 (d, 1H), 4.67 (d, 1H), 4.32-4.22 (m, 2H), 4.09-3.98 (m, 2H), 3.86 (d, 1H), 3.70 (t, 2H), 3.52 (dd, overlapping with solvent), 3.34-3.27 (m, overlapping with solvent), 3.01 (s, 3H), 2.93-2.84 (m, 1H), 2.74-2.67 (m, 1H).

Example 95

[Figure (not displayed)]

The compound was synthesized analogous to the procedure of Example 91 starting from tert-butyl (R)-6-(3-(2-methoxyethyl)morpholino)quinoline-4-carboxylate Intermediate 201 (0.093 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol). The compound was purified by preparative SFC, PrepMethod SFC-A followed by preparative HPLC, PrepMethod F, to give the title compound (0.031 g, 25%); HRMS (ESI) m/z [M+H]+ calcd for C23H28N5O4S: 470.1856, found: 470.1846; 1H NMR (600 MHz, DMSO-d6) δ 8.95 (t, 1H), 8.62 (d, 1H), 7.87 (d, 1H), 7.59-7.56 (m, 2H), 7.36 (d, 1H), 5.26 (dd, 1H), 4.85 (d, 1H), 4.67 (d, 1H), 4.30 (dd, 1H), 4.22 (dd, 1H), 4.05-4.00 (m, 1H), 3.93 (dd, 1H), 3.84 (d, 1H), 3.66-3.63 (m, 2H), 3.58-3.48 (m, overlapping with solvent), 3.46-3.42 (m, overlapping with solvent), 3.39-3.29 (m, overlapping with solvent), 3.28-3.21 (m, 1H), 3.17-3.10 (m, overlapping with solvent), 3.09 (s, 3H), 1.97-1.88 (m, 1H), 1.65-1.57 (m, 1H).

Example 96

[Figure (not displayed)]

The compound was synthesized and purified analogous to the procedure of Example 91 starting from tert-butyl 6-((2S,3S)-3-(methoxymethyl)-2-methylmorpholino)quinoline-4-carboxylate Intermediate 204 (0.093 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) to give the title compound (0.030 g, 25%); HRMS (ESI) m/z [M+H]+ calcd for C23H28N5O4S: 470.1856 found: 470.1848; 1H NMR (600 MHz, DMSO-d6) δ 8.96 (t, 1H), 8.63 (d, 1H), 7.87 (d, 1H), 7.63-7.58 (m, 2H), 7.36 (d, 1H), 5.26 (dd, 1H), 4.85 (d, 1H), 4.67 (d, 1H), 4.29 (dd, 1H), 4.22 (dd, 1H), 4.05-3.98 (m, 1H), 3.88 (td, 1H), 3.83-3.80 (m, 1H), 3.67-3.61 (m, overlapping with solvent), 3.42-3.28 (m, overlapping with solvent), 3.17 (dd, 1H), 3.15-3.12 (m, 5H), 1.35 (d, 3H).

Example 97

[Figure (not displayed)]

The compound was synthesized analogous to the procedure of Example 91 starting from tert-butyl 6-((2R,3R)-3-(methoxymethyl)-2-methylmorpholino)quinoline-4-carboxylate Intermediate 207 (0.093 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol). The compound was purified by preparative SFC, PrepMethod SFC-A, followed by PrepMethod SFC-D, to give the title compound (0.045 g, 36%); HRMS (ESI) m/z [M+H]+ calcd for C23H28N5O4S: 470.1856 found: 470.1856; 1H NMR (600 MHz, DMSO-d6) δ 8.96 (t, 1H), 8.63 (d, 1H), 7.87 (d, 1H), 7.65 (d, 1H), 7.61 (dd, 1H), 7.37 (d, 1H), 5.27 (dd, 1H), 4.85 (d, 1H), 4.67 (d, 1H), 4.26 (d, 2H), 4.05-3.98 (m, 1H), 3.87 (td, 1H), 3.84-3.78 (m, 1H), 3.69-3.61 (m, 2H), 3.43-3.27 (m, overlapping with solvent), 3.19 (td, 1H), 3.15 (s, 3H), 1.35 (d, 3H).

Example 98

[Figure (not displayed)]

The compound was synthesized and purified analogous to the procedure of Example 91 starting from tert-butyl 6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)quinoline-4-carboxylate Intermediate 208 (0.085 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) to give the title compound (0.054 g, 49%); HRMS (ESI) m/z [M+H]+ calcd for C22H24N5O3S: 438.1594, found: 438.1606; 1H NMR (500 MHz, DMSO-d6) δ 8.99 (t, 1H), 8.62 (d, 1H), 7.88 (d, 1H), 7.71 (d, 1H), 7.57 (dd, 1H), 7.35 (d, 1H), 5.29 (dd, 1H), 4.89 (d, 1H), 4.69 (d, 1H), 4.43-4.36 (m, 2H), 4.29 (d, 2H), 3.78 (dd, 2H), 3.50 (dd, 2H), 3.43-3.34 (m, overlapping with solvent), 2.04-1.93 (m, 4H).

Example 99

[Figure (not displayed)]

The compound was synthesized and purified analogous to the procedure of Example 91 starting from tert-butyl 6-(1,9-dioxa-4-azaspiro[5.5]undecan-4-yl)quinoline-4-carboxylat Intermediate 209 (0.096 g, 0.25 mmol) and (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (0.062 g, 0.30 mmol) to give the title compound (0.029 g, 24%); HRMS (ESI) m/z [M+H]+ calcd for C24H28N5O4S: 482.1856, found: 482.1846; 1H NMR (600 MHz, DMSO-d6) δ 8.99 (t, 1H), 8.64 (d, 1H), 7.87 (d, 1H), 7.70 (d, 1H), 7.64 (dd, 1H), 7.36 (d, 1H), 5.26 (dd, 1H), 4.85 (d, 1H), 4.67 (d, 1H), 4.32-4.22 (m, 2H), 3.80 (t, overlapping with solvent), 3.62-3.54 (m, overlapping with solvent), 3.39-3.31 (m, overlapping with solvent), 3.28-3.18 (m, overlapping with solvent), 1.81-1.72 (m, 2H), 1.71-1.62 (m, 2H).

US11858924B2. N-(2-(4-cyanothiazolidin-3-yl)-2-oxoethyl)-quinoline-4-carboxamides (2024-01-02). AstraZeneca AB [SE]. Inventors: Jonas Brånalt [SE], Maria Johansson [SE], Anneli Nordqvist [SE], Marianne Swanson [SE].
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Patent 2024
5
Synthesis of 7-Bromo-4-(1H-imidazol-1-yl)-2-(thiophen-2-yl)quinoline and Derivatives
Not available on PMC !

Example 27

[Figure (not displayed)]

Step 1: N-(2-Acetyl-5-bromophenyl)thiophene-2-carboxamide. 1-(2-Amino-4-bromophenyl)ethan-1-one (214 mg, 1.00 mmol) was placed in a flask with dichloromethane (5 mL) and triethylamine (0.15 mL, 1.10 mmol) then cooled to 0° C. Thiophene-2-carbonyl chloride (147 mg, 1.10 mmol) was added dropwise. The reaction was warmed to r.t. and stirred for 16 h. The volatiles were removed and the resulting solids were triturated with dichloromethane, filtered and vacuum dried to afford N-(2-acetyl-5-bromophenyl)thiophene-2-carboxamide as a solid (MS: [M+1]+ 323.9).

Step 2: 7-Bromo-2-(thiophen-2-yl)quinolin-4-ol. N-(2-acetyl-5-bromophenyl)thiophene-2-carboxamide (250 mg, 0.77 mmol) was placed in a flask with dioxane (10 mL). Sodium hydroxide (108 mg, 2.7 mmol) was added and the mixture heated to 110° C. for 2 h. Ethanol (2 mL) was added and the resulting solids filtered off. The filtrate was concentrated to dryness. Water (4 mL) and hexanes (1 mL) were added and the mixture was stirred for 5 minutes. The solution was acidified with HCl (1.0 N aq.) and the resulting solids filtered and vacuum dried to afford 7-bromo-2-(thiophen-2-yl)quinolin-4-ol as a solid (MS: [M+1]+ 306.0).

Step 3: 7-Bromo-4-chloro-2-(thiophen-2-yl)quinoline. 7-Bromo-2-(thiophen-2-yl)quinolin-4-ol (180 mg, 0.59 mmol) was placed in a flask with phosphorus oxychloride (3 mL). The reaction was heated to 110° C. for 3 h. After cooling to r.t., ice was added. The aqueous portion was extracted with ethyl acetate (2×5 mL) and the combined organics dried (Na2SO4) then concentrated to afford 7-bromo-4-chloro-2-(thiophen-2-yl)quinoline (MS: [M+1]+ 323.9).

Step 4: 7-bromo-4-(1H-imidazol-1-yl)-2-(thiophen-2-yl)quinoline. 7-Bromo-4-chloro-2-(thiophen-2-yl)quinoline (65 mg, 0.2 mmol) was placed in a flask with imidazole (34 mg, 0.50 mmol), potassium t-butoxide (34 mg, 0.30 mmol), Bis(triphenylphosphine)palladium(II) dichloride (7 mg, 0.01 mmol) and DMA (3 mL) under N2. The mixture was heated at 110° C. for 2 h. After cooling down to room temperature, the crude was diluted by EtOAc (20 mL) and washed by water (5 mL×2) and brine (5 mL×2). The organic phase was concentrated and purified by column chromatography on silica gel to give 7-bromo-4-(1H-imidazol-1-yl)-2-(thiophen-2-yl)quinoline as a solid (MS: [M+1]+ 356.0).

The following compounds are prepared essentially by the same method described above to prepare I-380.

MS
I-#Starting MaterialStructure[M + 1]+
I-381[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
380.0
I-382[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
380.0
I-1[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
306.1
I-275[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
382.1
I-383[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
351.0
I-384[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
351.0
I-385[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
364.0
I-50[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
340.0

US11873291B2. Quinoline cGAS antagonist compounds (2024-01-16). ImmuneSensor Therapeutics, Inc. [US], The Board of Regents of the University of Texas System [US]. Inventors: Jian Qiu [US], Qi Wei [US], Matt Tschantz [US], Heping Shi [US], Youtong Wu [US], Hulling Tan [US], Lijun Sun [US], Chuo Chen [US], Zhijian Chen [US].
Full text: Click here
Patent 2024

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More about "Quinoline"

Quinoline is a heterocyclic organic compound consisting of a benzene ring fused to a pyridine ring.
It is widely utilized in the synthesis of pharmaceuticals, dyes, and other chemical products.
Quinoline derivatives exhibit a diverse range of biological activities, including antimalarial, antibacterial, antifungal, and anticancer properties.
Researchers in the field of quinoline chemistry often leverage PubCompare.ai's AI-driven platform to optimize their reproducible research protocols, easily locate relevant protocols from literature, pre-prints, and patents, and identify the best protocols and products through AI-driven comparisons.
PubCompare.ai's precise and efficient tools can help streamline quinoline research and accelerate the development of new therapeutic agents.
Quinoline-based compounds are structurally similar to other heterocyclic molecules, such as isoquinoline and acridine, which are also used in various applications.
These related compounds share common structural features and can exhibit overlapping biological activities.
Researchers may utilize techniques like DMSO (dimethyl sulfoxide) solubilization, FBS (fetal bovine serum) supplementation, and FACSCalibur flow cytometry to investigate the effects of quinoline derivatives on cell lines and animal models.
In the process of quinoline research, scientists often employ analytical techniques like GraphPad Prism 5 for data analysis, Luna C18 columns for HPLC purification, and APEX2 software for crystallographic structure determination.
Additionally, solvents like acetonitrile and reagents like SADABS may be used in the synthesis and characterization of quinoline compounds.
Streptomycin, a broad-spectrum antibiotic, has also been studied in combination with quinoline derivatives for potential synergistic antimicrobial effects.
By leveraging PubCompare.ai's AI-driven platform, researchers can optimize their quinoline research protocols, streamline the identification of relevant literature and pre-prints, and make informed decisions on the best protocols and products to use in their studies.
This can lead to more efficient and reproducible research, ultimately accelerating the development of new quinoline-based therapeutic agents.