- Efficient, straightforward, catalyst-free synthesis of medicinally important S-alkyl/benzyl dithiocarbamates under green conditions
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Green synthesis of some novel dithiocarbamate derivatives substituted by aliphatic and aromatic groups as potentially interesting, medicinally important organic compounds via efficient one-pot, catalyst-free reaction is described. In this reaction, dithiocarbamate derivatives are obtained from condensation reaction between primary or secondary amines, carbon disulfide, and alkyl or benzyl halides in one pot and ethanol–aqueous medium. Among aliphatic and aromatic amines, the results generally show that reaction of aliphatic amines with alkyl or benzyl halides led to desired products in highest yields. Also, among aliphatic amines, those which reacted with benzyl halides showed better yields than those that reacted with alkyl halides. Use of environmentally benign solvents is one of the advantages of this procedure. Also, obtaining products in good yield via catalyst-free reaction using a facile, inexpensive, and practical approach can be considered other advantages of this procedure. Target products are very important compounds, because their analogs have been applied in pharmaceutical, chemical, and rubber industries.
- Asadipour, Ali,Shams, Zeynab,Eskandari, Khalil,Moshafi, Mohammad-Hassan,Faghih-Mirzaei, Ehsan,Pourshojaei, Yaghoub
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p. 1295 - 1304
(2017/10/30)
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- Antimicrobial activities of some synthesized 1-(3-(2-methylphenyl)-4-Oxo-3H-quinazolin-2-yl-4-(substituted)thiosemicarbazide derivatives
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The substituted thiosemicarbazide moiety was placed at the C-2 position and 2-methylphenyl group at N-3 position of quinazoline ring and obtained compounds were tested for their antitubercular activities and antibacterial activities against selected gram-positive and gram-negative bacteria. The target compounds 1-(3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides were obtained by the reaction of 2-hydrazino-3-(2-methylphenyl) quinazolin-4(3H)-one with different dithiocarbamic acid methyl ester derivatives. All synthesized compounds were also screened for their antimicrobial activity against selective gram-positive and gram-negative bacteria by agar dilution method. Among the series, 1-[3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl]-4-[4-chlorophenyl]-thiosemicarbazide exhibited the most potent activity against S. typhi, E. coli, and B. subtilis, while 1-[3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl]-4-[4-nitrophenyl]-thiosemicarbazide was the most potent against E. coli, B. subtilis, P. aeruginosa, S. typhi, and S. flexneri. These two compounds exhibited the antitubercular activity at the minimum concentration (3 μg/mL) that offered potential for further optimization and development of new antitubercular agents. The obtained results demonstrated promising antimicrobial and antitubercular activities of the synthesized quinazoline compounds which could be used as new scaffolds for improving their antimicrobial activity.
- Alagarsamy,Anjana,Sulthana,Parthiban,Solomon, V. Raja
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p. 332 - 339
(2016/07/06)
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- Design, synthesis and antimicrobial activities of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazide derivatives
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A new series of 1-(4-oxo-3-(4-fluorophenyl)-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides (AR1-AR10) were obtained by the reaction of 2-hydrazino-3-(4-fluorophenyl) quinazolin-4(3H)-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-(4-fluorophenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one (4) was obtained by reacting 4-fluoroaniline (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2) and condensed with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated for the favorable nucleophilic displacement reaction with hydrazine hydrate, which afford 2-hydrazino-3-(4-fluorophenyl)-3H-quinazolin-4-one (6). All synthesized compounds (AR1-AR10) were also screened for their antimicrobial activity against selective gram positive and gram negative by agar dilution method. In the present study compounds AR8 and AR9 were emerged as the most active compounds of the series.
- Alagarsamy,Appani, Ramgopal,Sulthana,Narendar,Solomon, V. Raja
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p. 2856 - 2860
(2016/10/12)
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- Design, synthesis and biological evaluation of novel HSP70 inhibitors: N, N′-disubstituted thiourea derivatives
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As novel heat shock protein 70 (HSP70) inhibitors, N, N′-disubstituted thiourea derivatives were designed and synthesized based on the X-ray structure of the ATPase domain (nucleotide binding domain, NBD). An ATPase activity inhibition assay revealed that these compounds effectively inhibited HSP70 ATPase activity. The results revealed that the compounds 370/371/374/379/380//392/394/397/404/405 and 407 can inhibit the HSP70 ATPase turnover with high percentages of inhibition: 50.42, 38.46, 50.45, 44.12, 47.13, 50.50, 40.95, 65.36, 46.23, 35.78, and 58.37 in 200 μM, respectively. Significant synergies with lapatinib were observed for compound 379 and compound 405 in the BT474 breast cancer cell line. A structure-function analysis revealed that most of the thiourea derivatives exhibited cooperative action with lapatinib in the BT474 cancer cell line and the BT/LapR1.0 lapatinib-resistant cell line. HSP70 inhibitors may be developed as synergetic drugs in drug-resistant cancer therapy.
- Zeng, Yan-Qun,Cao, Rui-Yuan,Yang, Jian-Ling,Li, Xing-Zhou,Li, Song,Zhong, Wu
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- Synthesis and Anticonvulsant Activity Evaluation of 4-Phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one and Its Derivatives
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A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones (6a-x) with triazole and other heterocyclic substituents (7-14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices (PIs) that were much higher than those of currently used drugs (PI6o > 25.5, PI6q > 26.0). Compounds 6o and 6q showed significant oral activity against MES-induced seizures in mice, with ED50 values of 88.02 and 94.6 mg/kg, respectively. The two compounds were also found to have potent activity against seizures that were induced by pentylenetetrazole and bicuculline. A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones with triazole and other heterocyclic substituents were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity using maximal electroshock and rotarod neurotoxicity tests.
- Zhang, Hong-Jian,Jin, Peng,Wang, Shi-Ben,Li, Fu-Nan,Guan, Li-Ping,Quan, Zhe-Shan
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p. 564 - 574
(2015/08/06)
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- Syntheses and antimicrobial activities of 1-(3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)-4-(substituted) thiosemicarbazide derivatives
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A series of 1-(3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)-4- (substituted) thiosemicarbazides (AS1-AS10) were obtained by the reaction of 3-benzyl-2-hydrazino-3H-quinazolin-4-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate, 3-benzyl-2-thioxo-2,3- dihydro-1H-quinazolin-4-one (4), was obtained by the reaction of benzyl amine (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulphate to yield the dithiocarbamic acid methyl ester 2 and condensation with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated in the favourable nucleophilic displacement reaction with hydrazine hydrate, which afforded 3-benzyl-2-hydrazino-3H-quinazolin-4-one (6). The IR, and 1H- and 13C-NMR spectra of these compounds showed the presence of peaks due to thiosemicarbazides, carbonyl (C=O), NH and aryl groups. The molecular ion peaks of the quinazolin-4-one moiety (m/z 144) were observed in all the mass spectra of the compounds AS1-AS10. Elemental (C, H, N) analysis satisfactorily confirmed purity and elemental composition of the synthesized compounds. All the synthesized compounds were screened for their antimicrobial activity against selective gram positive and gram negative bacteria by agar dilution method. In the present study, compounds AS8 and AS9 emerged as the most active compounds of the series.
- Alagarsamy, Veerachamy,Solomon, Viswas Raja,Krishnamoorthy,Sulthana,Narendar
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p. 1471 - 1479
(2016/02/18)
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- Synthesis and characterization of new (E)-N'-(substituted benzylidene)-2-(3-(2-methyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio) acetohydrazides
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A small library of new azomethine derivatives of 3-aryl-2-thioxo-2,3- dihydroquinazolin-4(1H)-ones was synthesized. The key intermediates 2-thioxo-quinazolinones (3a-e), obtained in 2 steps from the corresponding anilines, were treated with methyl chloroa
- Saeed, Aamer,Mahmood, Shams-Ul,Floerke, Ulrich
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p. 275 - 287
(2014/04/03)
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- Design and synthesis of novel 2-(3-substituted propyl)-3-(2-methyl phenyl) quinazolin-4-(3H)-ones as a new class of H1-antihistaminic agents
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A series of novel 2-(3-substituted propyl)-3-(2-methyl phenyl) quinazolin-4-(3H)-ones were synthesized by the reaction of 2-(3-bromopropyl thio)-3-(2-methyl phenyl) quinazolin-4-(3H)-one with various amines. The starting material, 2-(3-bromopropyl thio)-3
- Alagarsamy,Parthiban
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- Synthesis and pharmacological evaluation of some 3-(2-methylphenyl)-2- substituted amino-quinazolin-4(3H)-ones as analgesic and anti-inflammatory agents
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A variety of novel 3-(2-methylphenyl)-2-substituted amino-quinazolin-4(3H)- ones were synthesized by reacting the amino group of 2-hydrazino-3-(2- methylphenyl)-quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(2-methylphenyl)-quinazolin-4(3H)-one was synthesized from 2-methyl aniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. Among these, the compound 2-(1-ethylpropylidene)-hydrazino-3-(2-methylphenyl)-quinazolin-4(3H)- one emerged as the most active compound for analgesic activity, while the compound 2-(1-methylbutylidene)-hydrazino-3-(2-methylphenyl)-quinazolin-4(3H)- one showed most potent anti-inflammatory activity of the series and was moderately more potent in its anti-inflammatory activity when compared to the reference standard diclofenac sodium (CAS 15307-86-5). Interestingly, the test compounds showed only mild ulcerogenic potential when compared to acetylsalicylic acid (CAS No: 50-78-2). ECV - Editio Cantor Verlag.
- Alagarsamy, Veerachamy,Solomon, Viswas Raja,Murugesan, Sankaranarayanan
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p. 174 - 181
(2008/09/19)
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- Synthesis and pharmacological investigation of novel 4-(2-methylphenyl)-1-substituted-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-o nes as new class of H1-antihistaminic agents
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A series of novel 1-substituted-4-(2-methylphenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-o nes were synthesized by the cyclization of 2-hydrazino-3-(2-methylphenyl)-3H-quinazolin-4-one with various one carbon donors. The starting material 2-hydrazino-3-(2
- Alagarsamy,Rupeshkumar,Kavitha,Meena,Shankar,Siddiqui,Rajesh
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p. 2331 - 2337
(2008/12/23)
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