Synthesis and biological evaluation of some novel 6-aryl-2-(p- sulfamylphenyl)-4,5-dihydropyridazin-3(2H)-ones as anti-cancer, antimicrobial, and anti-inflammatory agents

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 2, 2010, Pages 266-271

  Ahmad, Shamim ^a   Rathish, I G ^a   Bano, Sameena ^a   Alam, M S ^a   Javed, Kalim ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

Anti cancer; Anti inflammatory; Antimicrobial; Benzenesulfonamides; Pyridazinones

Indexed keywords

6 (2 HYDROXY 5 METHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (2,5 DIMETHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (3 CHLORO 4 HYDROXYPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 CHLOROPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 ETHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 HYDROXY 2 METHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 HYDROXY 3 METHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 METHOXYPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 (4 METHYLPHENYL) 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZINE 3(2H) ONE; 6 PHENYL 2 (P SULFAMYLPHENYL) 4,5 DIHYDROPYRIDAZIN 3(2H) ONE; ALCOHOL; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; BENZENESULFONAMIDE DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; CANCER CELL CULTURE; CLINICAL PROTOCOL; CONFERENCE PAPER; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; LEUKEMIA; LUNG NON SMALL CELL CANCER; POLYMERIZATION; PRIORITY JOURNAL;

ANTI-INFLAMMATORY AGENTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; BACTERIAL INFECTIONS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INFLAMMATION; MYCOSES; NATIONAL CANCER INSTITUTE (U.S.); NEOPLASMS; PYRIDAZINES; SULFONAMIDES; UNITED STATES;

EID: 77949445492     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903155781     Document Type: Conference Paper

References (21)

1. Coates WJ. In: Katritzky AR, Rees CW, Scriven EFV, eds. Comprehensive Heterocyclic Chemistry (Vol. 2): Pyridazines and their benzo derivatives, Exeter, UK: Elsevier, 1996:1-91.
2. Tisler M, Stanovnik B, eds. Advances in Heterocyclic Chemistry, Vol.49. London, Academic Press, 1990:385-472.
3. Kuroda S, Akahane A, Itani H, Nishimura S, Durkin K, Kinoshita T, et al. Discovery of FR166124, a novel water-soluble pyrazolo-[1,5-a] pyridine adenosine A1 receptor antagonist. Bioorg Med Chem Lett 1999;9:1979-1984.
4. Costantino L, Rastelli G, Cignarella G, Barlocco D. Synthesis and aldose reductase inhibitory activity of a new series of benz[h]cinnolinone derivatives. Farmaco 2000;55:544-552
5. Kwon SK, Moon A. Synthesis of 3-alkylthio-6-allylthiopyridazine derivatives and their antihepatocarcinoma activity. Arch Pharm Res 2005;28:391-394
6. Sönmez M, Berber ?, Akba? E. Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes. Eur J Med Chem 2006;41:101-105
7. Harris RR, Black L, Surapaneni S, Kolasa T, Majest S, Namovic MT, et al. ABT-963 [2-(3,4-difluoro-phenyl)-4-(3-hydroxy-3-methyl-butoxy) 5-(4-methanesulfonyl-phenyl)-2H-pyridazin-3-one], a highly potent and selective disubstituted pyridazinone cyclooxgenase-2 inhibitor. J Pharmacol Exp Ther 2004;311:904-912
8. Krungkrai J, Supuran CT. The alpha-carbonic anhydrase from the malaria parasite and its inhibition. Curr Pharm Des 2008;14:631-640
9. Scozzafava A, Briganti F, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem 2000;43:292-300.
10. Chohan ZH, Shaikh AU, Rauf A, Supuran CT. Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin. J Enzyme Inhib Med Chem 2006;21:741-748
11. Chohan ZH, Metal-based sulfonamides: their preparation, characterization,and in-vitro antibacterial, antifungalcytotoxic properties. X-ray structure of 4-[(2-hydroxybenzylidene) amino] benzenesulfonamide. J Enzyme Inhib Med Chem 2008;3:120-130
12. Kim SJ, Jeong HJ, Choi IY, Lee KM, Park RK, Hong SH, et al. Cyclooxygenase-2 inhibitor SC-236 [4-[5-(4-chlorophenyl)-3- (trifluoromethyl)-1- pyrazol-1-l]benzenesulfonamide] suppresses nuclear factor-kappaB activation and phosphorylation of p38 mitogenactivated protein kinase, extracellular signal-regulated kinase, and c-Jun N-terminal kinase in human mast cell line cells. J Pharmacol Exp Ther 2005;314:27-34.
13. Khanna IK, Weier RM, Yu Y, Collins PW, Miyashiro JM, Koboldt CM, et al. 1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase-2. J Med Chem 1997;40:1619-1633
14. Khan MSY, Siddiqui AA. Syntheses and anti-inflammatory activity of some 6-aryl-2,3,4,5-tetrahydro-3-pyridazinones. Ind J Chem 2000;39B:614-619
15. Khan MSY, Hussain A, Sharma S. Studies on butenolides: 2-arylidene-4- (substituted aryl)but-3-en-4-olides-synthesis, reactions and biological activity. Indian J Chem 2002;41B:2160-2171
16. Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757-766
17. Boyd MR, Paull KD. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev Res 1995;34:91-109.
18. Boyd MR. In: Teicher BA, ed. Cancer Drug Discovery and Development: Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval. Totowa, NJ: Humana Press, 1997:23-43.
19. Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med 1962;111:544-547
20. Rathish IG, Kalim Javed, Ahmad S, Bano S, Alam MS, Pillai KK, et al. Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide. Bioorg Med Chem Lett 2009;19:255-258
21. Bisen PS, Verma K, eds. Handbook of Microbiology. Shahdara, Delhi, India: CBS Publishers and Distributors, 1994.