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> Chemicals & Drugs > Organic Chemical > Quinazolines

Quinazolines

Quinazolines are a class of heterocyclic organic compounds that consist of a quinazoline ring system.
These compounds have a wide range of biological activities and are used in the development of various pharmaceutical agents, including antidepressants, antimalarials, and anticancer drugs.
Quinazoline derivatives have also been studied for their potential therapeutic applications in the treatment of neurodegenerative disorders, inflammation, and other medical conditions.
Researchers can leverage PubCompare.ai, an AI-driven platform, to optimize their Quinazoline research by locating the best protocols from literature, preprints, and patents, and identifying the most reliable and effective Quinazoline-related products and methods.
This tool can enhance the reproducibility and accuracy of Quinazoline research, taking it to new heights.

Most cited protocols related to «Quinazolines»

1
DNA Cleavage Assay for Bacterial Topoisomerase IV
Cited 9 times
DNA cleavage reactions were carried out using the procedure of Fortune and Osheroff (41 (link)). Reactions contained 200 nM wild-type or mutant topoisomerase IV and 10 nM negatively supercoiled pBR322 in a total of 20 μL of cleavage buffer [40 mM Tris–HCl (pH 7.9), 10 mM MgCl2, 50 mM NaCl, and 2.5% (v/v) glycerol]. In some reactions, the concentration dependence of MgCl2 was examined or the divalent metal ion was replaced with either CaCl2 or MnCl2. Reaction mixtures were incubated at 37 °C for 10 min, and enzyme-DNA cleavage complexes were trapped by the addition of 2 μL of 5% SDS followed by 1 μL of 250 mM EDTA (pH 8.0). Proteinase K (2 μL of a 0.8 mg/mL solution) was added, and samples were incubated at 45 °C for 45 min to digest the enzyme. Samples were mixed with 2 μL of agarose gel loading buffer, heated at 45 °C for 5 min, and subjected to electrophoresis in 1% agarose gels in 40 mM Tris-acetate (pH 8.3) and 2 mM EDTA containing 0.5 μg/mL ethidium bromide. DNA bands were visualized and quantified as described above. DNA cleavage was monitored by the conversion of supercoiled plasmid to linear molecules.
Assays that monitored the DNA cleavage activities of wild-type and mutant B. anthracis topoisomerase IV in the absence of drugs substituted 1 mM CaCl2 for 10 mM MgCl2 in the cleavage buffer. Assays that assessed the DNA cleavage activities of the wild-type and mutant enzymes in the presence of drugs contained 0-30 μM compound for the wild-type enzyme and 0-500 μM compound for the mutant enzymes.
For assays that monitored competition between ciprofloxacin (0-150 μM) and 8-methyl-quinazoline-2,4-dione (20 μM), the level of cleavage seen with the corresponding concentration of ciprofloxacin in the absence of the quinazolinedione was used as a baseline and was subtracted from the cleavage level seen in the presence of both compounds. Ciprofloxacin and 8-methyl-quinazoline-2,4-dione were added simultaneously to reaction mixtures.
Aldred K.J., McPherson S.A., Wang P., Kerns R.J., Graves D.E., Turnbough CL J.r, & Osheroff N. (2011). Drug Interactions with Bacillus anthracis Topoisomerase IV: Biochemical Basis for Quinolone Action and Resistance. Biochemistry, 51(1), 370-381.
Publication 2011
Acetate Bacillus anthracis Biological Assay Buffers Ciprofloxacin compound 30 Cytokinesis DNA Cleavage DNA Topoisomerase IV Edetic Acid Electrophoresis Endopeptidase K Enzymes Ethidium Bromide Gels Glycerin Magnesium Chloride manganese chloride Metals Multienzyme Complexes Pharmaceutical Preparations Plasmids Quinazolinediones Quinazolines Sepharose Sodium Chloride Tromethamine Vision
2
Persistence of Topoisomerase IV-DNA Cleavage
Cited 9 times
The persistence of topoisomerase IV-DNA cleavage complexes established in the presence of drugs was determined using the procedure of Gentry et al. (46 (link)). Initial reaction mixtures contained 1 μM wild-type or mutant topoisomerase IV, 50 nM DNA, and 20 μM (for the wild-type enzyme) or 200 μM (for the mutant enzymes) ciprofloxacin or 20 μM 8-methyl-quinazoline-2,4-dione in a total of 20 μL of DNA cleavage buffer. Reactions were incubated at 37 °C for 10 min and then diluted 20-fold with DNA cleavage buffer warmed to 37 °C. Samples (20 μL) were removed at times ranging from 0-300 min, and DNA cleavage was stopped with 2 μL of 5% SDS followed by 1 μL of 250 mM EDTA (pH 8.0). Samples were digested with proteinase K and processed as described above for plasmid cleavage assays. Levels of DNA cleavage were set to 100% at time zero, and the persistence of cleavage complexes was determined by the decay of the linear reaction product over time.
Aldred K.J., McPherson S.A., Wang P., Kerns R.J., Graves D.E., Turnbough CL J.r, & Osheroff N. (2011). Drug Interactions with Bacillus anthracis Topoisomerase IV: Biochemical Basis for Quinolone Action and Resistance. Biochemistry, 51(1), 370-381.
Publication 2011
Biological Assay Buffers Ciprofloxacin Cytokinesis DNA Cleavage DNA Topoisomerase IV Edetic Acid Endopeptidase K Enzymes Pharmaceutical Preparations Plasmids Quinazolines
3
Synthesis of 3-Amino-quinazolinone Derivatives
Cited 6 times
3-Amino-quinazolinone derivatives were prepared according to the procedures shown in Scheme 1 (18 ). Then quinazoline derivatives were treated with chloroacetyl chloride in the presence of dichloromethane/triethylamine to afford the 2-chloro -N-(4-oxo-2-quinazolin3 (3H)-yl) acetamide derivatives. Final products were synthesized by the reaction of 2-chloro -N-(4-oxo-2-quinazolin3 (3H)-yl) acetamide derivatives with 4-mehyl-4-H-1, 2, 4-triazole- 3-thiol in dry acetone and potassium carbonate (19 20 ).
Hassanzadeh F., Sadeghi-aliabadi H., Nikooei S., Jafari E, & Vaseghi G. (2019). Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids. Research in Pharmaceutical Sciences, 14(2), 130-137.
Publication 2019
acetamide Acetone chloroacetyl chloride derivatives Methylene Chloride potassium carbonate Quinazolines Quinazolinones Sulfhydryl Compounds Triazoles triethylamine
4
Investigating the Role of BDNF and VEGFR2 in Songbird Vocal Plasticity
Cited 4 times
Our experimental design is summarized in Figure 1. Untreated females were first recorded for 2 weeks to ensure that they were not singing spontaneously. Afterward, between experimental days 1–7 (Fig. 1), birds were injected intraperitoneally twice daily with 50 μg of 5-bromo-2′-deoxyuridine (BrdU) per gram of body weight (Sigma) in 0.9% saline. On day 8, HVC was tranfected bilaterally with a BDNF plasmid expression vector (100 nl/hemisphere) under isoflurane anesthesia. Additional females were given BDNF plasmid injections bilaterally into the robust nucleus of the arcopallium (RA) or into the nidopallium adjacent to the HVC. To control for the surgery and the plasmid injection, other females underwent either a sham operation or were injected with an empty plasmid not containing the BDNF sequence into the HVC. After surgery, all birds were implanted with SILASTIC tubes (Dow Corning) containing either testosterone propionate (Sigma) or nothing (empty SILASTICs). Between days 8 and 34, females were injected intramuscularly with either VEGFR2-I (inhibitor of vascular endothelial growth factor receptor tyrosine kinase) (4-[(4′-chloro-2′-fluoro)phenylamino]-6,7-dimethoxy-quinazoline [Calbiochem]; 2.5 μg of VEGFR2-I per gram of body weight) dissolved in vehicle (DMSO/PBS, 2:1) or either the DMSO/PBS vehicle or PBS only. Because vehicle and PBS females did not differ in their measurements, we collectively refer to them as PBS-treated throughout this paper. At day 26, all SILASTIC implants were renewed. On day 44, the birds were killed by an overdose of isoflurane and perfused transcardially with 50 ml each of 0.9% saline and 4% formaldehyde solution. The brains were removed, postfixed in 4% formaldehyde for 1 week, and then cryoprotected in 10% sucrose for 5 d and 20% sucrose for 3 d. The right hemisphere was cut on a freezing microtome into 40 μm sagittal sections, and the left hemisphere was stored at −80°C.
An additional set of females (“BDNF only”) was injected with BrdU and given BDNF plasmid as above but was not treated with either testosterone or VEGFR2-I. Another set of females was treated as above, except for the date when the animals were killed (four “T+VEGFR2-I+BDNF” females and four “T+VEGFR2-I” females; the latter received an empty plasmid). Each of the latter was randomly assigned to one of the former, and each female was maintained single in a sound box. One day after start of singing of the T+VEGFR2-I+BDNF females, these females and their nonsinging matched control females were killed.
Hartog T.E., Dittrich F., Pieneman A.W., Jansen R.F., Frankl-Vilches C., Lessmann V., Lilliehook C., Goldman S.A, & Gahr M. (2009). Brain-Derived Neurotrophic Factor Signaling in the HVC Is Required for Testosterone-Induced Song of Female Canaries. The Journal of Neuroscience, 29(49), 15511-15519.
Publication 2009
5-bromouridine Anesthesia Animals Aves Body Weight Brain Cell Nucleus Cloning Vectors Drug Overdose Females Formaldehyde Formalin Isoflurane Microtomy Normal Saline Operative Surgical Procedures Plasmids Quinazolines Silastic Sound Sucrose Sulfoxide, Dimethyl Testosterone Testosterone Propionate Vascular Endothelial Growth Factor Receptor Vascular Endothelial Growth Factor Receptor-2 Woman
5
Synthesis of Benzo[g]quinazoline Derivatives
Cited 3 times
The general procedures for the preparation of compounds 1–17 were previously reported for the preparation of their analogues [13 (link),17 (link)]. Briefly, in the basic medium, the reaction of ethyl(methyl)isothiocyanate with 3-amino-2-naphthaoic acid under a refluxing condition in DMF for 3–5 h afforded the parent intermediates 1 and 2 in good yields (Scheme 1). When compound 1 or 2 was treated with the appropriate alkyl/heteroalkyl halide in the presence of a base at 80 °C for 20 h, benzo[g]quinazolines 3–15 were obtained in good to high yields. Hydrazinolysis of 1 and 2 in boiling DMF for 15–18 h afforded 16 and 17, respectively. Their characterization data are reported herein as follows:
Abuelizz H.A., Marzouk M., Bakheit A.H., Awad H.M., Soltan M.M., Naglah A.M, & Al-Salahi R. (2020). Antiproliferative and Antiangiogenic Properties of New VEGFR-2-targeting 2-thioxobenzo[g]quinazoline Derivatives (In Vitro). Molecules, 25(24), 5944.
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Publication 2020
Amino Acids compound 17 methyl isothiocyanate Parent Quinazolines

Most recents protocols related to «Quinazolines»

1
Synthesis of Organoselenium Compounds via Ugi Reaction
Not available on PMC !

Example 1

The target organoselenium compound 5 is synthesized using the Ugi four components reaction. The synthesis starts by the reaction of quinazoline-2-carbaldehyde (1) (1 mmol) with 4-(methylselanyl)aniline (2) (1 mmol) followed by the addition of 2-((3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)thio)acetic acid (3) (1 mmol) and 2-isocyano-2-methylpropane (4) (1.2 mmol). The reaction proceeds smoothly at room temperature in methanol as solvent.

[Figure (not displayed)]

It is to be understood that the organic selenide compounds and the use thereof with DPPD are not limited to the specific embodiments described above, but encompasses any and all embodiments within the scope of the generic language of the following claims enabled by the embodiments described herein, or otherwise shown in the drawings or described above in terms sufficient to enable one of ordinary skill in the art to make and use the claimed subject matter.

US11878960B1. Antioxidant therapeutic potential of N,N′-diphenyl-1,4-phenylenediamine and a novel selenide on minimizing breast cancer hazards (2024-01-23). KING FAISAL UNIVERSITY [SA]. Inventors: Hany Mohamed Abd El-Lateef Ahmed [SA], Saadeldin Elsayed Ibrahim Shabaan [SA], Mai Mostafa Khalaf Ali [SA], Mohamed Gouda [SA], Shady Gamal El-Sawah [SA], Ibrahim Youssef [SA], Sameh M. Shabana [SA].
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Patent 2024
4-phenylenediamine Acetic Acid Anabolism aniline Antioxidants diphenyl Gene, BRCA1 Generic Drugs Methanol N,N'-diphenyl-4-phenylenediamine Organic Chemicals Organoselenium Compounds Quinazolines Solvents Therapeutics
2
Synthesis and Characterization of Copper(I) Complex
This was synthesized following a modified literature procedure.28 (link) Ph2P(2-quinazoline) (123 mg, 0.4 mmol) and [Cu(MeCN)4]PF6 (97 mg, 0.26 mmol) were added to 1 dram vial. MeCN (1 ml) was added and the resulting yellow solution was stirred at r.t. (21 h), during which some product may form and give a yellow suspension. Further Et2O may be added to precipitate more product. The precipitated solids were isolated via filtration and washed with Et2O (5 ml) to give the crude product as a yellow powder that fluorescence orange (8.1 mg, 5.8 μmol, 11% yield). It may be further purified by redissolving it in minimal MeCN and precipitating with Et2O twice.
δH (400 MHz, CDCl3, ppm) 9.94 (br s), 8.29 (br s), 8.09 (t, J = 7.7 Hz), 7.94 (br s), 7.87 (t, J = 7.1 Hz), 7.16 (br s), 7.09 (br s).
δP{H} (162 MHz, CDCl3, ppm): 10.68 (br s), −144.03 (sept, PF6−).
δC (101 MHz, CDCl3, ppm) 161.44, 149.10, 137.14, 133.14, 131.02, 130.80, 128.89, 128.22.
HRMS(ESI+): [C2H3CuN]+m/z = 103.9554, calcd = 103.9562. [C60H45CuN6P3]+m/z = 1005.2242, calcd = 1005.2215. [C40H30CuN4P2]+m/z = 691.1262, calcd = 691.1242. [C22H18CuN3P]+m/z = 418.0545, calcd = 418.0534. [C20H15CuN2P]+m/z = 377.0271, calcd = 377.0269.
Feng H., Luo S.X., Croy R.G., Essigmann J.M, & Swager T.M. (2023). Interaction of N-nitrosamines with binuclear copper complexes for luminescent detection. Dalton Transactions (Cambridge, England : 2003), 52(10), 3219-3233.
Publication 2023
Filtration Fluorescence Powder Quinazolines
3
Synthesis and Characterization of Novel Oxo-TB Compounds
Oxo-TB 21a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 8.78 (1H, ddt, 8.6, 1.3, 0.7, H9), 8.13 (1H, d, 8.9, H4), 7.91 (1H, br d, 8.2, H6), 7.87 (1H, br d, cov., H18), 7.86 (1H, br d, cov., H21), 7.81 (1H, d, 8.8, H16), 7.64 (1H, d, 8.9, H3), 7.64 (1H, ddd, 8.6, 7.0, 1.4, H8), 7.56 (1H, ddd, 8.5, 6.8, 1.3, H20), 7.52 (1H, d, 8.8, H15), 7.49 (1H, ddd, 8.1, 6.9, 1.2, H7), 7.48 (1H, ddd, 8.1, 6.9, 1.2, H19), 5.28 (1H, d, 17.3, H13 exo), 5.06 (1H, dd, 12.6, 1.5, H12a), 5.01 (1H, br d, 17.3, H13endo), 4.98 (1H, d, 12.6, H12b). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C, from HSQC and HMBC): 173.83 (C11), 154.16 (C2), 140.41 (C14), 135.44 (C4), 131.87 (C10), 131.02 (C17), 130.88 (C5), 130.58 (C22), 128.51 (C6), 128.49 (C18), 128.27 (C8), 127.36 (C16), 126.75 (C20), 126.32 (C9), 125.58 (C19), 125.39 (C7), 124.86 (C15), 124.74 (C23), 122.89 (C3), 121.92 (C21), 115.07 (C1), 64.34 (C12), 51.36 (C13). HRMS (APCI+, MeOH): for C23H16N2O calcd. [M + H]+ 337.1335 found 337.1339. HRMS (ESI+): for C23H16N2O calcd. [M + H]+ 337.1335, too low intensity (<5%); calcd. for [M + Na]+ 359.1155 found 359.1157 (100%); calcd. [2M + Na]+ 695.2418, found 695.2417 (5%); calcd. [3M + Na]+ 1031.3680, found 1031.3695.
Dihydroquinazoline 7a: identified according to the characteristic singlet at 5.46 ppm (2H, s) having an HSQC correlation to the 13C signal at 45.28 ppm from the CH2 group (an HMBC correlation to the 13C signal at 146.66 ppm), and the singlet at 8.09 ppm (1H, br s) having an HSQC correlation to the 13C signal at 146.66 ppm from the N=CH-N group. HRMS (APCI+, MeOH): for C22H16N2 calcd. [M + H]+ 309.1386, found 309.1388.
Oxo-quinazoline 22a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 9.83 (1H, ddt, 8.6, 1.3, 0.7, H9), 8.71 (1H, s, H12), 8.41 (1H, br d, 8.8, H4), 8.20 (1H, br d, 2.2, H13), 8.14 (1H, br d, 8.0, H6), 8.13 (1H, dq, 8.7, 0.7, H16), ~8.08 (1H, m, H18), ~8.05 (1H, m, H21), 7.83 (1H, d, 8.8, H3), 7.78 (1H, ddd, 8.6, 6.9, 1.6, H8), 7.74 (1H, dd, 8.7, 2.2, H15), 7.72 (1H, ddd, 8.0, 6.9, 1.3, H7), 7.68–7.63 (2H, m, H19 and H20). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 160.71 (C11), 150.26 (C2), 148.22 (C12), 136.05 (C4), 135.57 (C14), 132.94 (C22), 132.57 (C17), 131.79 (C5), 130.49 (C10), 128.75 (C6 or C8), 128.73 (C8 or C6), 128.70 (C16), 128.12 (C21), 127.76 (C18), 127.16 (C19), 126.91 (C20), 126.83 (C7), 126.43 (C9), 126.18 (C13), 126.15 (C3), 125.80 (C15), 115.12 (C1). HRMS (APCI+, MeOH): for C22H14N2O calcd. [M + H]+ 323.1179, found 323.1172. HRMS (ESI+): for C22H14N2O calcd. [M + H]+ 323.1179, found 323.1182 (70%); calcd. for [M + Na]+ 345.0998 found 345.1001 (93%); calcd. [2M + Na]+ 667.2105, found 667.2107 (100%); calcd. [3M + Na]+ 989.3211, found 989.3223 (23%).
SpiroTB 4a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.85 (1H, m, H6), 7.77 (1H, d, 8.8, H4), 7.73 (1H, m, H9), 7.42 (1H, m, cov., H8), 7.41 (1H, m, cov., H7), 7.39 (1H, m, cov., H21), 7.36 (1H, m, cov., H20), 7.35 (1H, m, cov., H18), 7.34 (1H, m, cov., H3), 7.34 (1H, m, cov., H19), 7.02 (1H, d, 9.8, H16), 6.01 (1H, d, 9.8, H15), 5.09 (1H, d, 17.8, H13a), 4.89 (1H, d, 17.8, H13b), 3.85 (1H, br d, 12.6, H12a), 3.67 (1H, dd, 12.6, 1.8, H12b), 3.44 (1H, br d, 17.2, H11a), 2.93 (1H, d, 17.2, H11b). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 166.99 (C14), 144.54 (C2), 143.04 (C22), 133.89 (C16), 131.84 (C10), 131.65 (C17), 130.26 (C5), 129.00 (C20), 128.31 (C6), 128.12 (C18), 127.40 (C4), 127.31 (C19), 126.58 (C15), 126.55 (C8), 124.97 (C3), 124.73 (C21), 124.63 (C7), 122.74 (C1), 122.16 (C9), 73.33 (C13), 48.67 (C12), 38.76 (C11), 35.59 (C23). HRMS (APCI+, MeOH): for C23H18N2 calcd. [M + H]+ 323.1543, found 323.1547. M.p. 84–86 °C decomp. (from methanol) did not match any of the bases isolated by Farrar [10 (link)].
Unidentified hydroxy-TB 23a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 5.84 (1H, br d, 5.2, H11), 6.90 (d, 5.2, OH), 4.77 (1H, d, 12.4, 1.6, H12a), 4.40 (1H, d, 12.4, H12b), 4.96 (1H, d, 16.9, H13a), 4.70 (1H, br d, 16.9, H13b). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 82.83 (C11), 60.08 (C12), 54.25 (C13). HRMS (APCI+, MeOH): for C23H18N2O calcd. [M + H]+ 339.1492, found 339.1494.
Havlík M., Navrátilová T., Drozdová M., Tatar A., Lanza P.A., Dusso D., Moyano E.L., Chesta C.A., Vera D.M, & Dolenský B. (2023). Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines. Molecules, 28(4), 1549.
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Publication 2023
1H NMR Carbon-13 Magnetic Resonance Spectroscopy Methanol Quinazolines Sulfoxide, Dimethyl
4
Synthesis and Characterization of Quinazolines
Quinazoline 6a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.85 (1H, ddt, 8.4, 1.1, 0.8, H9), 7.77 (1H, ddt, 9.1, 0.8, 0.5, H16), 7.73 (1H, dddd, 8.1, 1.3, 0.8, 0.5, H18), 7.71 (1H, ddt, 8.0, 1.4, 0.7, H6), 7.66 (1H, ddt, 8.2, 1.2, 0.8, H21), 7.55 (1H, dd, 8.7, 2.5, H4), 7.55 (1H, dd, 9.1, 2.5, H15), 7.46 (1H, ddd, 8.3, 6.8, 1.4, H8), 7.39 (1H, dd, 2.5, 0.5, H13), 7.36 (1H, ddd, 8.2, 6.8, 1.3, H20), 7.24 (1H, ddd, 8.1, 6.8, 1.2, H19), 7.23 (1H, ddd, 8.0, 6.8, 1.1, H7), 6.90 (1H, d, 8.7, H3), 6.46 (1H, br t, 3.6, NH), 4.89 (2H, br s, H11), 4.83 (2H, d, 3.6, H12). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 146.89 (C14), 141.49 (C2), 134.31 (C22), 131.65 (C10), 128.52 (C16), 128.34 (C6), 127.79 (C17), 127.24 (C4), 127.23 (C18), 127.12 (C5), 126.43 (C8), 126.39 (C21), 126.11 (C20), 122.96 (C19), 121.58 (C7), 120.47 (C9), 119.35 (C3), 118.40 (C15), 110.30 (C13), 109.17 (C1), 59.32 (C12), 47.53 (C11). HRMS (APCI+, MeOH): for C22H18N2 calcd. [M + H]+ 311.1543, found 311.1543. M.p. 100–102 °C (from ethanol).
Bisquinazoline 16a: 1H NMR (500 MHz, DMSO-d6, 20.5 °C): 8.05 (2H, br d, 8.5, H9), 7.84 (2H, dd, 8.0, 1.4, H6), 7.74 (2H, d, 8.8, H4), 7.67 (2H, br d, 8.1, H18), 7.58 (2H, d, 9.0, H16), 7.57 (2H, ddd, 8.5, 6.8, 1.4, H8), 7.57 (2H, d, 8.8, H3), 7.53 (2H, br d, 8.2, H21), 7.42 (2H, dd, 9.0, 2.5, H15), 7.40 (2H, ddd, 8.1, 6.8, 1.1, H7), 7.39 (2H, cov., H13), 7.31 (2H, ddd, 8.2, 6.8, 13, H20), 7.22 (2H, ddd, 8.1, 6.8, 1.2, H19), 5.13 (2H, br s, H23), 4.91 (4H, br s, H12), 4.90 (4H, br s, H11). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 146.42 (C14), 141.61 (C2), 134.28 (C22), 131.11 (C10), 128.46 (C16), 128.32 (C6), 128.24 (C5), 127.77 (C17), 127.64 (C4), 127.17 (C18), 126.75 (C8), 126.41 (C21), 126.10 (C20), 123.42 (C7), 123.00 (C19), 121.48 (C9), 119.25 (C3), 118.62 (C15), 115.55 (C1), 109.76 (C13), 68.71 (C23), 63.85 (C12), 48.02 (C11).
Naphthylamine 2a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.61 (1H, dtd, 8.1, 1.3, 0.7, H6), 7.57 (1H, br d, 8.7, H4), 7.49 (1H, dtd, 8.3, 1.2, 0.7, H9), 7.26 (1H, ddd, 8.3, 6.8, 1.3, H8), 7.08 (1H, ddd, 8.1, 6.8, 1.2, H7), 6.93 (1H, dd, 8.7, 2.3, H3), 6.81 (1H, ddd, 2.3, 0.8, 0.5, H1), 5.34 (2H, br s, 15N satellites 1JHN = 83.5, NH2). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 146.64 (C2), 135.00 (C10), 128.46 (C4), 127.45 (C6), 126.32 (C5), 125.83 (C8), 125.01 (C9), 120.83 (C7), 118.39 (C3), 105.79 (C1). HRMS (APCI+, MeOH): for C10H9N calcd. [M + H]+ 144.0808, found 144.0809.
Dinaphthylamine 17a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.76 (1H, d, cov., H9), 7.69 (1H, dd, 8.1, 1.4, H6), 7.64 (1H, d, cov., H17), 7.62 (1H, d, cov., H4), 7.62 (1H, d, cov., H20), 7.57 (1H, d, cov., H15), 7.35 1H, ddd, cov., H8), 7.32 (1H, ddd, 8.2, 6.8, 1.3, H19), 7.14 (1H, ddd, 8.1, 6.8, 1.1, H7), 7.11 (1H, ddd, 8.0, 6.8, 1.3, H18), 7.08 (1H, dd, 8.8, 2.3, H14), 7.07 (1H, d, cov., H3), 6.99 (1H, d, 2.3, H12), 5.85 (1H, br t, 4.5, NH), 4.50 (2H, d, 4.5, H11). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 147.25 (C13), 145.01 (C2), 135.24 (C21), 133.91 (C10), 128.48 (C4), 128.12 (C6), 127.97 (C15), 127.41 (C17), 127.01 (C5), 126.44 (C16), 126.30 (C8), 125.92 (C19), 125.43 (C20), 121.87 (C9), 120.86 (C18), 120.84 (C7), 119.10 (C3), 118.69 (C14), 110.40 (C1), 102.38 (C12), 38.79 (C11). HRMS (APCI+, MeOH): for C21H18N2 calcd. [M + H]+ 299.1543, found 299.1544.
Acridine 5a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 10.64 (1H, br s, H11), 9.44 (2H, ddt, 8.2, 1.2, 0.7, H9), 8.21 (2H, ddd, 9.1, 0.8, 0.5, H4), 8.12 (2H, br d, 7.8, H6), 8.06 (2H, dd, 9.1, 0.8, H3), 7.87 (2H, dddd 8.2, 7.1, 1.4, 0.3, H8), 7.79 (2H, ddd 7.8, 7.1, 1.2, H7). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 147.80 (C2), 132.16 (C4), 131.03 (C5), 129.86 (C10), 128.76 (C6), 127.84 (C7), 127.65 (C3), 127.63 (C8), 126.25 (C11), 124.27 (C9), 123.71 (C1). HRMS (APCI+, MeOH): for C21H13N calcd. [M + H]+ 280.1121, found 280.1120.
Bisnaphthylamine 18a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.95 (2H, ddt, 8.6, 1.2, 0.7, H9), 7.60 (2H, ddt, 8.0, 1.5, 0.5, H6), 7.45 (2H, br d, 8.7, H4), 7.15 (2H, ddd, 8.6, 6.8, 1.5, H8), 7.07 (2H, ddd, 8.0, 6.8, 1.1, H7), 6.99 (2H, d, 8.7, H3), 5.47 (2H, br s, NH2), 4.36 (2H, s, H11). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 143.81 (C2), 133.69 (C10), 131.79 (C1), 128.27 (C6), 127.46 (C5), 127.07 (C4), 125.62 (C8), 122.48 (C9), 120.62 (C7), 119.18 (C3), 23.33 (C11).
TB 3a: 1H NMR (500 MHz, DMSO-d6, 25 °C): 7.76 (2H, ddt 8.0, 1.4, 0.6, H6), 7.74 (2H, ddt 8.5, 1.2, 0.8, H9), 7.69 (2H, br d, 8.8, H4), 7.47 (2H, ddd, 8.5, 6.9, 1.4, H8), 7.38 (2H, d, 8.8, H3), 7.37 (2H, ddd, 8.0, 6.9, 1.2, H7), 4.96 (2H, dd, 16.8, 0.8, H11a), 4.72 (2H, br d, 16.8, H11b), 4.44 (2H, br s, H12). 13C{1H} NMR (126 MHz, DMSO-d6, 25 °C): 145.41 (C2), 130.93 (C10), 130.19 (C5), 128.26 (C6), 127.24 (C4), 126.44 (C8), 124.67 (C3), 124.57 (C7), 121.44 (C9), 121.23 (C1), 66.07 (C12), 55.16 (C11). HRMS (APCI+, MeOH): for C23H18N2 calcd. [M + H]+ 323.1543, found 323.1544. M.p. 208–210 °C (from ethanol).
Havlík M., Navrátilová T., Drozdová M., Tatar A., Lanza P.A., Dusso D., Moyano E.L., Chesta C.A., Vera D.M, & Dolenský B. (2023). Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines. Molecules, 28(4), 1549.
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Publication 2023
1H NMR Acridines Carbon-13 Magnetic Resonance Spectroscopy Ethanol Quinazolines Satellite Viruses Sulfoxide, Dimethyl
5
Radiolabeling of Quinazoline Derivatives
All solvents and laboratory chemicals were reagent grade and were used without further purification. The HPLC-grade solvents for high-performance liquid chromatography (HPLC) were degassed by a helium flux before and during use. IR spectra were recorded using the Brucker™ Alpha II™ FT-IR/ATR Spectrometer between 4000–400 cm−1. NMR spectra were recorded on a Bruker 250 MHz or 500 MHz Avance DRX spectrometer using the residual solvent peak as a reference. HPLC analysis was performed on a Waters 600 chromatography system coupled to a Waters 2487 Dual l Absorbance detector and a Gabi gamma detector from Raytest. Separations were achieved on a Nucleosil C18 (10 mm, 250 mm × 4 mm) column eluted with a binary gradient system at a 1 mL/min flow rate. Mobile phase A was methanol containing 0.1% trifluoroacetic acid, while mobile phase B was water containing 0.1% trifluoroacetic acid. The elution gradient was 0–1 min 95% B (5% A), followed by a linear gradient to 85% A (15% B) in 8 min. This composition was held for 17 min. After a column wash with 95% A for 10 min, the column was re-equilibrated by applying the initial conditions (95% B) for 10 min prior to the next injection.
[99mTc]NaTcO4 was obtained in physiological saline as a commercial 99Mo/99mTc generator eluate (Ultra-Technekow™ V4 Generator, Curium Pharma, Petten, Netherlands). 6-Amino-4-[(3-bromophenyl)amino] quinazoline (1) [21 (link),22 (link)], N-(2-pyridylmethyl)aminoethyl acetate (PAMA) (3) [23 (link)] and the rhenium precursors ReBr(CO)5 and fac-[Net4]2[ReBr3(CO)3] [24 (link)] as well as the radioactive precursor fac-[99mTc][Tc(OH2)3(CO)3]+ [25 (link)] have been synthesized according to the literature methods.
Makrypidi K., Kiritsis C., Roupa I., Triantopoulou S., Shegani A., Paravatou-Petsotas M., Chiotellis A., Pelecanou M., Papadopoulos M, & Pirmettis I. (2023). Evaluation of Rhenium and Technetium-99m Complexes Bearing Quinazoline Derivatives as Potential EGFR Agents. Molecules, 28(4), 1786.
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Publication 2023
Acetate ARID1A protein, human Chromatography Curium farnesyl-protein transferase-alpha Gamma Rays Helium High-Performance Liquid Chromatographies Infrared Spectrophotometry Laboratory Chemicals Methanol physiology Quinazolines Radioactivity Rhenium Saline Solution Solvents Trifluoroacetic Acid

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More about "Quinazolines"

Quinazolines are a diverse class of heterocyclic organic compounds featuring a quinazoline ring system.
These versatile molecules exhibit a wide range of valuable biological activities, making them integral to the development of various pharmaceutical agents, including antidepressants, antimalarials, and anti-cancer drugs.
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