Volume 8, Issue 4, October 2014, Pages 1798–1813
Deepak Kumar1, Roshan Lal2, and Sarita Rani3
1 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
2 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
3 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
Original language: English
Copyright © 2014 ISSR Journals. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
A series of 2-(5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazole-3-ylthio)-N-(substituted benzylidene) acetohydrazides (5a-5l) have been synthesized via condensation of 2-(5-(6-Bromo-2-methyl-4-oxaquinazolin-3 (4H)-yl)-4H-1,2,4-triazole-3-ylthio)acetohydrazide (4) with different aromatic aldehydes. Cycloaddition of thioglycolic acid with 5a-5l yielded 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(substituted benzylidene)-4-oxothiazolidin-3-yl) acetamides (6a-6l) while compound 5a-5l on treatment with chloro-acetylchloride in the presence of triethylamine are converted into 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(3-chloro-2-(substituted benzylidene)-4-oxoazetidin-1-yl) acetamides (7a-7l).The structure of all the newly synthesized compounds have been confirmed by elemental analysis and spectral studies (IR, 1H-NMR and mass spectroscopy).Compounds 5a-5l,6a-6l and 7a-7l have been evaluated for their anti-inflammatory and analgesic activity and were compared with the standard drug phenylbutazone. The most active compound of this series is 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(3-chloro(2,6-dichloro benzylidene)-4-oxoazetidin-1-yl) acetamide (7g).
Author Keywords: Thiazolidinonyl quinazolinone, Azetidinonyl quinazolinone, anti-inflammatory activity, Analgesic activity, acute toxicity.
Deepak Kumar1, Roshan Lal2, and Sarita Rani3
1 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
2 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
3 Medicinal Chemistry Division, Department of Chemistry, D.N.(P.G.)College, Meerut 250002(U.P), India
Original language: English
Copyright © 2014 ISSR Journals. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract
A series of 2-(5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazole-3-ylthio)-N-(substituted benzylidene) acetohydrazides (5a-5l) have been synthesized via condensation of 2-(5-(6-Bromo-2-methyl-4-oxaquinazolin-3 (4H)-yl)-4H-1,2,4-triazole-3-ylthio)acetohydrazide (4) with different aromatic aldehydes. Cycloaddition of thioglycolic acid with 5a-5l yielded 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(substituted benzylidene)-4-oxothiazolidin-3-yl) acetamides (6a-6l) while compound 5a-5l on treatment with chloro-acetylchloride in the presence of triethylamine are converted into 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(3-chloro-2-(substituted benzylidene)-4-oxoazetidin-1-yl) acetamides (7a-7l).The structure of all the newly synthesized compounds have been confirmed by elemental analysis and spectral studies (IR, 1H-NMR and mass spectroscopy).Compounds 5a-5l,6a-6l and 7a-7l have been evaluated for their anti-inflammatory and analgesic activity and were compared with the standard drug phenylbutazone. The most active compound of this series is 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(3-chloro(2,6-dichloro benzylidene)-4-oxoazetidin-1-yl) acetamide (7g).
Author Keywords: Thiazolidinonyl quinazolinone, Azetidinonyl quinazolinone, anti-inflammatory activity, Analgesic activity, acute toxicity.
How to Cite this Article
Deepak Kumar, Roshan Lal, and Sarita Rani, “Synthesis of some new substituted azetidinonyl and thiazolidinonyl quinazolon-4(3H)-ones as potential non-steroidal anti-inflammatory and analgesic agents,” International Journal of Innovation and Applied Studies, vol. 8, no. 4, pp. 1798–1813, October 2014.
