Synthesis of pyrazole-based 1,5-diaryl compounds as potent anti-inflammatory agents

Medicinal Chemistry Research

Volumn 21, Issue 9, 2012, Pages 2465-2475

  Shrivastava, Priyanka ^a   Singh, Praveen ^a   Tewari, Ashish Kumar ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

1,3 diarylpyrazole ester; Carrageenan induced rat paw edema; COX 2

Indexed keywords

5 [3 (1,3 DIOXO 1,3 DIHYDROISOINDOL 2 YL)PROPOXY] 3 METHYL 1 PHENYL 1H PYRAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 5 [3 (3 CYANO 4,6 DIMETHYLPYRIDIN 1 YLOXY)PROPOXY] 3 METHYL 1 PHENYL 1H PYRAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; ANTIINFLAMMATORY AGENT; CARRAGEENAN; CYCLOOXYGENASE 2; NIMESULIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION;

EID: 84866360348     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9774-2     Document Type: Article

References (25)

1. Almansa C, Alfon J, De Arriba A, Cavalcanti F, Escamilla I, Gomez L, Miralles oliva AR, Bartolli J, Carceller E, Merlos M, Garcia-Rafenell J (2003) Synthesis and Structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. J Med Chem 46:3463-3475 (Pubitemid 36909822)
2. 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 44B:2532-2537 (Pubitemid 43127857)
3. Avasthi K, Chandra T, Bhakuni DS (1995) A convenient and general synthesis of 1, w-bis (4,6-dimethyl-thio-1H-pyrazolo [3,4-d] pyrimidin-l-yl) alkanes and their regioisomers. Indian J Chem 34B:944-949
4. Carter JS (2000) Inhibitors of cyclooxygenase-2: November 1999-April 2000. Expert Opin Ther Pathol 10:1011-1020 (Pubitemid 30420883)
5. Dannhardt G, Kiefer W (2001) Cyclooxygenase inhibitors-current status and future prospects. European J Med Chem 36:109-126 (Pubitemid 32304514)
6. Dannhardt G, Laufer S (2000) Structural approaches to explain the selectivity of COX-2 inhibitors: Is there a common pharmacophore? Curr Med Chem 7:1101-1112
7. Di Rosa M, Giroud JP, Willoughby DA (1971) Studies of the mediators of the acute inflammatory response induced in rats in different sites by carrageenan and turpentine. J Pathol 104:15-29
8. Garcia-Leme J (1978) Bradykininsystem. In: Vane JR, Ferreira SH (eds) Handbook of experimental pharmacology, vol 50/I. Springer, Berlin, p 464
9. Gursoy A, Demirayak S, Capan G, Erol K, Vural K (2000) Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Euro J Med Chem 35:359-364 (Pubitemid 30187068)
10. Hla T, Neilson K (1992) Human cyclooxygenase-2 cDNA. Proc Nati Acad Sci USA 89:7384-7388
11. Holsapple MP, Schnur M, Yim GKW (1980) Pharmocological modulation of edema mediated by prostaglandin, serotonin and histamine. Agents and Actions 10:368-373 (Pubitemid 11195283)
12. Insel PA (1996) Analgesic, antipyretic and anti-inflammatory agents and drugs employed in the treatment of gout. In: Hardman JG, Limbird LE (eds) Goodman & Gilman's the pharmacological basis of therapeutics. McGraw-Hill, New York, pp 617-657
13. Kulkarni SK, Mehta AK, Kunchandy J (1986) Anti-inflammatory actions of clonidine, guanfacine and B-HT 920 against various inflammagen-induced acute paw oedema in rats. Arch Int Pharmacodyn 279:324-334 (Pubitemid 16124979)
14. Kumar A, Sharma S, Bajaj K, Bansal D, Sharma S, Archana K, Saxena KK, Lata S, Gupta B, Srivastava VK (2003) Synthesis and anti-inflammatory, analgesic, ulcerogenic and cyclooxygenase activities of novelquinasolinyl- pyrazolines. Indian J Chem 42:1979-1984
15. Leonard NJ (1979) Stacking interaction between tryptophan and uracil in a synthetic model compound. Acc Chem Res 12:423-429
16. Lombardino JG, Otterness KK, Wiseman EH (1975) Acidic antiinflammatory agents-correlations of some physical, pharmacological and clinical data. Arzneimittel-Forschung 25:1629-1635
17. Meyer EA, Castellano RK, Diederich F (2003) Interactions with aromatic rings in chemical and biological recognition. Angew Chem Int Ed Eng 42:1210-1250 (Pubitemid 36410287)
18. Reynold JEF (1993) The extra pharmacopoeia. In: Reynold JEF (ed) Martindale, 30th edn. Pharmaceutical Press, London, p 1
19. Talley JJ (1999) Selective inhibitors of cyclooxygenase-2 (COX-2). Prog Med Chem 36:201-234
20. Tewari AK, Mishra A (2001) Synthesis and anti-inflammatory activities of N4,N5-disubstituted-3-methyl-1H-pyrazolo[3,4-c]pyridazines. Bioorganic Med Chem 9:715-718
21. Tewari AK, Dubey R, Mishra A (2009) 2-substituted-8-methyl-3, 6-dihydroimidazo [4,5-c] pyrazolo[3,4-e]pyridazine as an Antiinflammatory agent. Med Chem Res (2011) 20:16-22
22. Tewari AK, Srivastava P, Singh VP, Singh A, Goel RK, Gopimohan C (2010a) Novel anti-inflammatory agents based on pyrazole based dimeric compounds; design, synthesis, docking and in vivo activity. Chem Pharm Bull Japan 58:634-638
23. Tewari AK, Srivastava P, Singh VP, Puerta C, Valerga P (2010b) Condensed phase conformational isomerisation of 5-[3-(1, 3-Dioxo-1,3-dihydro-isoindol-2- yl)-propoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester. Arkivoc (ix): 127-136
24. Vinegar R, Schreiber W, Hugo R (1969) Biphasic development of Carrageenan edema in rats. J Pharmacol Exp Ther 166:96-103
25. Wintar CA, Risley EA, Nuss GW (1962) Carragenin-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc Soc Exp Biol 111:544