Synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-Antibacterial agents

Medicinal Chemistry Research

Volumn 21, Issue 11, 2012, Pages 3396-3405

  Kumar, Pawan ^a   Chandak, Navneet ^a   Kaushik, Pawan ^a   Sharma, Chetan ^a   Kaushik, Dhirender ^a   Aneja, Kamal R ^a   Sharma, Pawan K ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

Anti inflammatory activity; Antibacterial activity; Pyrazoles; Thiazoles; Thiosemicarbazones

Indexed keywords

2 ([1 [4 (AMINOSULFONYL)PHENYL] 3 (4 CHLOROPHENYL) 1H PYRAZOL 4 YL]METHYLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; 2 ([1 [4 (AMINOSULFONYL)PHENYL] 3 (4 FLUOROPHENYL) 1H PYRAZOL 4 YL]METHYLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; 2 ([1 [4 (AMINOSULFONYL)PHENYL] 3 (4 METHOXYPHENYL) 1H PYRAZOL 4 YL]METHYLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; 2 ([1 [4 (AMINOSULFONYL)PHENYL] 3 (4 METHYLPHENYL) 1H PYRAZOL 4 YL]METHYLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; 2 ([1 [4 (AMINOSULFONYL)PHENYL] 3 PHENYL 1H PYRAZOL 4YL]METHYLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; 4 (3 (4 CHLOROPHENYL) 4 [[2 (4 (4 CHLOROPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 CHLOROPHENYL) 4 [[2 (4 (4 METHYLPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 CHLOROPHENYL) 4 [[2 (4 PHENYL 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 FLUOROPHENYL) 4 [[2 (4 (4 METHYLPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 FLUOROPHENYL) 4 [[2 (4 PHENYL 1,3 THIAZOL 2 YL)HYDRAZONO] METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 METHOXYPHENYL) 4 [[2 (4 (4 METHYLPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 METHOXYPHENYL) 4 [[2 (4 PHENYL 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 METHYLPHENYL) 4 [[2 (4 (4 METHYLPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 (4 METHYLPHENYL) 4 [[2 (4 PHENYL 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL]1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (3 PHENYL 4 [[2 (4 PHENYL 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (4 [[2 (4 (4 CHLOROPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL 3 (4 FLUOROPHENYL) 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (4 [[2 (4 (4 CHLOROPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 3 (4 METHOXY PHENYL) 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (4 [[2 (4 (4 CHLOROPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 3 (4 METHYLPHENYL) 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (4 [[2 (4 (4 CHLOROPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 3 PHENYL 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; 4 (4 [[2 (4 (4 METHYLPHENYL) 1,3 THIAZOL 2 YL)HYDRAZONO]METHYL] 3 PHENYL 1H PYRAZOL 1 YL)BENZENESULFONAMIDE; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; BENZENESULFONAMIDE DERIVATIVE; CARRAGEENAN; INDOMETACIN; PYRAZOLE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PAW EDEMA; RAT;

EID: 84871442324     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9853-4     Document Type: Article

References (39)

1. Ahmad I, Beg AJ (2001) Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multi-drug resistant human pathogens. J Ethnopharmacol 74:13-123
2. Anderson DW, Argentien DC, Ritchie DM, Katz LB, Shriver DA, Rosenthale ME, Capetola RJ (1990) Gastrointestinal (GI) profile of tepoxalin (TX), an orally active dual cyclooxygenase (CO)/lipoxygenase (LO) inhibitor with potent antiinflammatory activity. FASEB J 4:A1122
3. Andrews JM (2001) Determination of minimum inhibitory concentrations. Antimicrob Chemother 48:5-16
4. Banoglu E, Akoglu Ç, Unlu S, Kupeli E, Yesilada E, Sahin MF (2004) Amide derivatives of [6-(5-methyl-3-phenylpyrazole-1-yl)-3(2H)-pyridazinone-2- yl]acetic acids as potential analgesic and anti-inflammatory compounds. Arch Pharm Med Chem 337:7-14
5. Bekhit AA, Abdel-Azeim T (2004) Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-Antimicrobial agents. Bioorg Med Chem 12:1935-1945
6. Bekhit AA, Fahmy HTY (2003) Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory- Antimicrobial agents. Arch Pharm Med Chem 2:111-118
7. Bekhit AA, Fahmi HTY, Rostom SAF, Baraka AM (2003) Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4, 5-d]pyrimidines as anti-inflammatory-Antimicrobial agents. Eur J Med Chem 38:27-36
8. Bekhit AA, Ashour HMA, Guemei AA (2005) Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents. Arch Pharm Chem Life Sci 338:167-174
9. Bekhit AA, Rahman HMA, Guemei AA (2006) Synthesis and biological evaluation of some hydroxypyrazole derivatives as anti-inflammatory- Antimicrobial agents. Arch Pharm Chem Life Sci 339:81-87
10. Bekhit AA, Ashour HMA, Bekhit A, El-Din A, Abdel-Rahman HM, Bekhit SA (2009) Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents. J Enzyme Inhib Med Chem 24:296-309
11. Bondock S, Khalifa W, Fadda AA (2007) Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3, 4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 42:948-954
12. Dannhardt G, Keifer W (2001) Cyclooxygenase inhibitors -current status and future prospects. Eur J Med Chem 36:109-115
13. Foks H, Pancechowska-Ksepko D, Kedzia A, Zwolska Z, Janowiec M, Augustynowicz-Kopec E (2005) Synthesis and antibacterial activity of 1H-pyrazolo[3,4-b]pyrazine and -pyridine derivatives. II Farmaco 60:513-517
14. Giri RS, Thakar HM, Giordano T, Williams J, Rogers D, Sudersanam V, Vasu KK (2009) Design, synthesis and characterization of novel 2-(2,4-disubstituted- thiazole-5-yl)-3-Aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-jB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. Eur J Med Chem 44:2184-2189
15. Hantsch A, Weber JH (1887) Ueber verbindungen des thiazols (pyridins der thiophenreihe). Chem Ber 20:3118
16. Kalkhambkar RG, Kulkarni GM, ShivKumar H, Rao RN (2007) Synthesis of novel triheterocyclic thiazoles as anti-inflammatory and analgesic agents. Eur J Med Chem 42:1272-1276
17. Kameyama T, Nabeshima T (1978) Effects of 1,3-diphenyl-5-(2- dimethylaminopropionamide)-pyrazole[difenamizole] on a conditioned avoidance response. Neuropharmacology 17:249-256
18. Kameyama T, Ukai M, Nabeshima T (1978) Inhibitory effect of difenamizole on morphine induced straub tail reaction with special reference to monoamineergic agents. Chem Pharm Bull 26:3265-3270
19. Karegoudar P, Karthikeyan MS, Prasad DG, Mahalinga M, Holla BS, Kumari NS (2008) Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. Eur J Med Chem 43:261-267
20. Kouatly O, Geronikaki A, Kamoutsis C, Hadjipavlou-Litina DEle (2009) Adamantane derivatives of thiazolyl-N-substituted amide, as possible non-steroidal anti-inflammatory agents. Eur J Med Chem 44:1198-1204
21. LS NCC (2000) Method for dilution antimicrobial susceptibility test for bacteria that grow aerobically approved standards, 5th edn. National Committee for Clinical Laboratory Standards, Villanova
22. McFaraland J (1907) The nephelometer: An instrument for estimating the number of bacteria in suspensions used for calculating the opsonic index and for vaccines. J Am Med Assoc 14:1176-1178
23. Nussmeier NA, Whelton AA, Brown MT, Langford RM, Hoeft A, Parlow JL, Boyce SW, Verburg KM (2005) Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery. N Engl J Med 352:1081-1091
24. Penning TD, Talley JJ, Bertneshaw SR, Carten JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC (1997) Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] benze nesulfonamide (SC-58635, celecoxib). J Med Chem 40:1347-1365
25. Pillai AD, Rathod PD, Franklin PX, Patel M, Nivsarkar M, Vasu KK, Padh H, Sudarsanam V (2003) Novel drug designing approach for dual inhibitors as anti-inflammatory agents: implication of pyridine template. Biochem Biophys Res Commun 301:183-187
26. Prakash O, Kumar R, Parkash V (2008) Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-Aryl-4-pyrazolyl) chromones. Eur J Med Chem 43:435-440
27. Rosati O, Curini M, Marcotullio MC, Macchiarulo A, Perfumi M, Mattioli L, Rismondo F, Cravotto G (2007) Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2Hindazole derivatives. Bioorg Med Chem 15:3463-3473
28. Sawhney SN, Sharma PK (1993) Synthesis and antiinflammatory activity of some 3-heterocycle-1,2-benzisothiazoles. Bioorg Med Chem Lett 3:1551-1554
29. Scheen AJ (2004) Withdrawal of rofecoxib (Vioxx): what about cardiovascular safety of COX-2 selective non-steroidal antiinflammatory drugs Rev Med Liege 59:565-569
30. Shamroukh AH, Zaki MEA, Morsy EMH, Abdel-Motti FM, Abdel-Megeid FME (2007) Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyranotriazolo-pyrimidine derivatives. Arch Pharm Chem Life Sci 340:345-351
31. Sharma PK, Sawhney SN (1993) Synthesis and antiinflammatory activity of some 1,4-dihydro-3-methyl-1-(2-thiazolyl)pyrazolo[ 4,3-c][1, 2]benzothiazine 5,5-dioxides. Bull Chem Soc Japan 66:3843-3846
32. Sharma PK, Sawhney SN (1997) Potent antiinflammatory 3-thiazole-4(5)- Acetic acids of 1,2-benzisothiazole. Bioorg Med Chem Lett 7:2427-2430
33. Sharma PK, Sawhney SN, Gupta A, Singh GB, Bani S (1998) Synthesis and antiinflammatory activity of some 3-(2-thiazolyl)-1, 2-benzisothiazoles. Indian J Chem 37B:376-381
34. Sharma PK, Kumar S, Kumar P, Kaushik P, Kaushik D, Dhingra Y, Aneja KR (2010) Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory-Antimicrobial agents. Eur J Med Chem 45:2650-2655
35. Sharma PK, Chandak N, Kumar P, Sharma C, Aneja KR (2011a) Synthesis and biological evaluation of some 4-functionalizedpyrazoles as antimicrobial agents. Eur J Med Chem 46:1425-1432
36. Sharma PK, Singh K, Kumar S, Kumar P, Dhawan SN, Lal S, Ulbrich H, Dannhardt G (2011b) Synthesis and anti-inflammatory evaluation of some pyrazolo[3,4-b]pyridines. Med Chem Res 20:239-244
37. Szabó G, Fischer J, Kis-Varga A, Gyires K (2008) New celecoxib derivatives as anti-inflammatory agents. J Med Chem 51:142-147
38. Venkatachalam SR, Salaskar A, Chattopadhyay A, Barik A, Mishra B, Gangabhagirathic R, Priyadarsini KI (2006) Synthesis, pulse radiolysis, and in vitro radioprotection studies of melatoninolipoamide, a novel conjugate of melatonin and a-lipoic acid. Bioorg Med Chem 14:6414-6419
39. Winter CA, Risley EA, Nuss GW (1962) Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med 111:544-547