Synthesis and pharmacological evaluation of 3-cyclohexyl-2-substituted hydrazino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents

Open access

Synthesis and pharmacological evaluation of 3-cyclohexyl-2-substituted hydrazino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents

A series of novel 3-cyclohexyl-2-substituted hydrazino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 3-cyclohexyl-2-hydrazino quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material, 3-cyclohexyl-2-hydrazino quinazolin-4(3H)-one, was synthesized from cyclohexyl amine. Title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic behavior. The compound 3-cyclohexyl-2-(1-methylbutylidene-hydrazino)-3H-quinazolin-4-one (4c) emerged as the most active compound of the series and is moderately more potent in its analgesic and anti-inflammatory activities compared to the reference standard diclofenac sodium. Interestingly, test compounds showed only mild ulcerogenic potential when compared to acetylsalicylic acid.

J. van Ryn and R. M. Botting, New insights into the mode of action of anti-inflammatory drugs, Inflamm. Res. 44 (1995) 1-10; DOI: 10.1007/BF01630479.

J. van Ryn, G. Trummlitz and M. Pairet, COX-2 selectivity and inflammatory processes, Curr. Med. Chem. 7 (2000) 1145-1161.

J. van Ryn, Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs, Nature: New Biol. 231 (1971) 232-235.

M. Beuck, Nonsteroidal antiinflammatory drugs: A new generation of cyclooxygenase inhibitors, Angew. Chem. Int. Ed. 38 (1999) 631-633; DOI: 10.1002/(SICI)1521-3773(19990301)38:5<631:: AID-ANIE631>3.0.CO;2-S.

V. Alagarsamy, R. Revathi, S. Vijayakumar and K. V. Ramseshu, Synthesis and pharmacological investigation of some novel 2,3-disubstituted quinazolin-4(3H)-ones as analgesic and antiinflammatory agents, Pharmazie 58 (2003) 233-236; DOI: 10.1002/chin.200330182.

V. Alagarsamy, A. Thangathirupathy, S. C. Mandal, S. Rajasekaran, S. Vijayakumar, R. Revathi, J. Anburaj, S. Arunkumar and S. Rajesh, Pharmacological evaluation of 2-substituted (1,3,4) thiadiazolo quinazolines, Indian J. Pharm. Sci. 68 (2006) 108-111.

A. E. Abdel-Rahman, E. A. Bakhite and E. A. Al-Taifi, Synthesis and antimicrobial testing of some new S-substituted-thiopyridines, thienopyridines, pyridothienopyrimidines and pyridothienotriazines, Pharmazie 58 (2003) 372-377; DOI: 10.1002/chin.200330182.

R. V. Chambhare, B. G. Khadse, A. S. Bobde and R. H. Bahekar, Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents, Eur. J. Med. Chem. 38 (2003) 89-100; DOI: 10.1002/chin.200328177.

N. A. Santagati, A. Caruso, V. M. C. Cutuli and F. Caccamo, Synthesis and pharmacological evaluation of thieno[2,3-d]pyrimidin-2,4-dione and 5H-pyrimido [5,4-b]indol-2,4-dione derivatives, Farmaco 50 (1995) 689-695.

V. Alagarsamy, V. R. Solomon, G. Vanikavitha, V. Paluchamy, M. R. Chandran, A. A. Sujin, A. Thangathiruppathy, S. Amuthalakshmi and R. Revathi, Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substituted quinazolin-4(3H) ones, Biol. Pharm. Bull. 25 (2002) 1432-1435; DOI: 10.1248/bpb.25.1432.

V. Alagarsamy, G. Murugananthan and R. Venkateshperumal, Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methyl-3-substituted quinazolin-4-(3H)-ones, Biol. Pharm. Bull. 26 (2003) 1711-1714; DOI: 10.1248/bpb.26.1711.

V. Alagarsamy, R. Rajesh, R. Meena, S. Vijaykumar, K. V. Ramseshu and T. Duraianandakumar, Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methylthio-3-substituted quinazolin-4(3H)-ones, Biol. Pharm. Bull. 27 (2004) 652-656; DOI: 10.1248/bpb.27.652.

V. Alagarsamy, V. Muthukumar, N. Pavalarani, P. Vasanthanathan and R. Revathi, Synthesis, analgesic and anti-inflammatory activities of some novel 2,3-disubstituted quinazolin-4(3H)-ones, Biol. Pharm. Bull. 26 (2003) 557-559; DOI: 10.1248/bpb.26.557.

S. K. Kulkarni, Heat and other physiological stress-induced analgesia: Catecholamine mediated and naloxone reversible response, Life Sci. 27 (1980) 185-188; DOI: 10.1016/0024-3205(80)90136-8.

R. E. Amour and D. L. Smith, A method for determinating loss of pain sensation. J. Pharm. Exp. Ther. 72 (1941) 74-78.

C. A. Winter, E. A. Risely and G. W. Nuss, Carregeenin induced oedema in hind paw of the rat as assay for antiinflammatory drugs, Exp. Biol. Med. 111 (1962) 544-547.

R. K. Goyal, A. Chakrabarti and A. K. Sanyal, The effect of biological variables on the anti-ulcerogenic effect of vegetable plantain banana, Planta Med. 29 (1985) 85-88; DOI: 10.1055/s-2007-969412.

M. Shay, S. A. Komarov, D. Fels, D. Meranze, H. Grunstein and H. Siplet, A simple method for the uniform production of gastric ulceration in the rats, Gastroenterology 5 (1945) 43-61.

A. K. Ganguly and O. P. Bhatnagar, Effect of bilateral adrenalectomy on production of restraint ulcers in the stomach of albino rats, Can. J. Phys. Pharmacol. 51 (1973) 748-750.

Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

Journal Information

IMPACT FACTOR 2017: 1.071
5-year IMPACT FACTOR: 1.623

CiteScore 2017: 1.46

SCImago Journal Rank (SJR) 2017: 0.362
Source Normalized Impact per Paper (SNIP) 2017: 0.642

Cited By


All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 173 173 24
PDF Downloads 31 31 5