Synthesis and pharmacological evaluation of some novel 2-pyrazolines bearing benzenesulfonamide as anti-inflammatory and blood glucose lowering agents

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1378-1385

  Ovais, Syed ^a   Bashir, Rafia ^a   Yaseen, Shafiya ^a   Rathore, Pooja ^a   Samim, Mohammed ^a   Javed, Kalim ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

Anti hyperglyceamic; Anti inflammatory; Pyrazoline; Sulfonamide

Indexed keywords

4 [3 (3 HYDROXYPHENYL) 5 (3,4,5 TRIMETHOXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 (3 HYDROXYPHENYL) 5 (4 METHOXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 (3 HYDROXYPHENYL) 5 P TOLYL 4,5 DIHYDRO PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 (3 HYDROXYPHENYL) 5 PHENYL 4,5 DIHYDRO PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 (3 HYDROXYPHENYL) 5 STYRYL 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (2 CHLOROPHENYL) 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (2 HYDROXYPHENYL) 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (3,4 DIMETHOXYPHENYL) 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (4 CHLOROPHENYL) 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (4 HYDROXYPHENYL) 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 ANTHRACEN 9 YL 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 FURAN 2 YL 3 (3 HYDROXYPHENYL) 4,5 DIHYDROPYRAZOL 1 YL]BENZENESULFONAMIDE; ANTIDIABETIC AGENT; ANTIINFLAMMATORY AGENT; BENZENESULFONAMIDE DERIVATIVE; CELECOXIB; CHALCONE; GLICLAZIDE; GLUCOSE; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; HYPERGLYCEMIA; IN VIVO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

EID: 84874108762     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0130-y     Document Type: Article

References (20)

1. Abramson SB, Greenberg JD (2008) Are NSAIDs and selective cyclo-oxygenase 2 inhibitors associated with increased risk of myocardial infarction? Nat Clin Pract Rheumatol 4(4):182-183
2. Ahn JH, Kim HM, Jung SH, Kang SK, Kim KR, Rhee SD, Yang SD, Cheon HG, Kim SS (2004) Synthesis and DP-IV inhibition of cyano-pyrazoline derivatives as potent anti-diabetic agents. Bioorg Med Chem Lett 14(17):4461-4465
3. Amir M, Kumar S (2005) Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of 3,5-dimethyl pyrazoles, 3-methyl pyrazol-5-ones and 3,5-disubstituted pyrazolines. Indian J Chem, Sect B: Org Chem Incl Med Chem 44B(12):2532-2537
4. Ansari LF, Iftikhar F, Ihsan-ul-Haq, Mirza B, Baseer M, Rashid U (2008) Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines. Bioorg Med Chem 16:7691-7697 (and references cited there in)
5. Bashir R, Ovais S, Yaseen S, Hamid H, Alam MS, Samim M, Singh S, Javed K (2011) Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzenesulfonamide as anticancer and anti-inflammatory agents. Bioorg Med Chem Lett 21:4301-4305
6. Daidone G, Maggio B, Raffa D, Plescia S, Bajardi ML, Caruso A, Cutuli VMC, Amico-Roxas M (1994) Synthesis and pharmacological study of ethyl 1-methyl-5-[2-substituted-4-oxo-3(4H)-quinazolinyl]-1H-pyrazole-4-acetates. Eur J Med Chem 29(9):707
7. Dannhardt G, Kiefer W (2001) Cyclooxygenase inhibitors - current status and future prospects. Eur J Med Chem 36(2):109-126
8. Flower RJ (2003) The development of COX2 inhibitors. Nat Rev Drug Discov 2(3):179-191
9. Gursoy S, Demirayak G, Capan K, Erol K, Vural (2000) Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Eur J Med Chem 35(3):359-364
10. Inman WH (1977) Study of fatal bone marrow depression with special reference to phenylbutazone and oxyphenbutazone. Br Med J 1(6075):1500-1505
11. Kujubu DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR (1991) TIS10, a phorbol ester tumor promoter inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue. J Biol Chem 266:12866-12872
12. Kumar S, Sharma K, Bajaj D, Bansal S, Sharma K, Archana K, Saxena S, Lata B, Gupta VK, Srivastava (2003) Synthesis and anti-inflammatory, analgesic, ulcerogenic and cyclooxygenase activities of novel quinazolinyl-Δ2- pyrazolines. Indian J Chem, Sect B: Org Chem Incl Med Chem 42(8):1979-1984
13. Leonard JC (1953) Toxic effects of phenylbutazone with special reference to disorders of the blood. Br Med J 13(4823):1311-1313
14. Pospisilik JA, Stafford SG, Demuth HU, Brownsey R, Parkhouse W, Finegood DT, McIntosh CH, Pederson RA (2002) Long-term treatment with the dipeptidyl peptidase IV inhibitor P32/98 causes sustained improvements in glucose tolerance, insulin sensitivity, hyperinsulinemia, and beta-cell glucose responsiveness in VDF (fa/fa) Zucker rats. Diabetes 51(4):943-950
15. Rathish IG, Javed K, Ahmad S, Bano S, Alam MS, Pillai KK, Singh S, Bagchi V (2009) Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzenesulfonamide. Bioorg Med Chem Lett 19:255-258
16. Reynold JEFF (ed) (1993) The extra pharmacopia, 30th edn. Pharmaceutical Press, Martindale, p 1
17. Sudre B, Broqua P, White RB, Ashworth D, Evans DM, Haigh R, Junien JL, Aubert ML (2002) Chronic inhibition of circulating dipeptidyl peptidase IV by FE 999011 delays the occurrence of diabetes in male zucker diabetic fatty rats. Diabetes 51(5):1461-1469
18. Vane JR, Botting RM (1998) Anti-inflammatory drugs and their mechanism of action. Inflamm Res 47:78-87
19. Winter CA, Risley EA, Nuss GW (1962) Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc Soc Exp Biol Med 111:544-547
20. Xie WL, Chipman JG, Robertson DL, Erikson RL, Simmons DL (1991) Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc Natl Acad Sci USA 88(7):2692-2696