New thiazolidinyl analogs containing pyridine ring: Synthesis, biological evaluation and QSAR studies

Medicinal Chemistry Research

Volumn 22, Issue 4, 2013, Pages 1538-1548

  Ranga, Reetu ^a   Sharma, Vikas ^a   Kumar, Vipin ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

Analgesic activity; Anti inflammatory; COX 2 inhibitors; Docking; QSAR

Indexed keywords

2 (2 CHLORO,4 NITROPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2 CHLOROPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2 METHYLPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2 NITROPHENYLIMINO) 5 (1H PYRIDINE 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2,4 DINITRO PHENYLHYDRAZINYLIDINE) 5 (1H PYRIDIN 2 YL METHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2,4 DINITROPHENYLHYDRAZINYLIDINE) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (2,6 DIMETHYLPHENYLIMINO) 5 (1H PYRIDINE 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (3 METHYLPHENYLIMINO) 5 (1H PYRIDINE 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (3 NITRO PHENYLIMINO) 5 (1H PYRIDIN 2 YL METHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (3 NITROPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (4 BROMOPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (4 CHLOROPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (4 FLUOROPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (4 METHOXYPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (4 METHYLPHENYLIMINO) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 (PHENYLHYDRAZINYLIDINE) 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 2 [4 METHYLPHENYLIMINO] 5 (1H PYRIDIN 2 YLMETHYLIDENE) 1,3 THIAZOLIDIN 4 ONE; 5 (1H PYRIDIN 2 YLMETHYLIDENE) 2 (PHENYLIMINO) 1,3 THIAZOLIDIN 4 ONE; CYCLOOXYGENASE 2; DICLOFENAC; PYRIDINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; INFRARED SPECTROSCOPY; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

EID: 84879684485     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0149-0     Document Type: Article

References (32)

1. Balzarini J, Stevens M, Clercq ED, Schols D, Pannecouque C (2005) Pyridine N-oxide derivatives: unusual anti-HIV compounds with multiple mechanisms of antiviral action. J Antimicrob Chemother 55:135-138
2. Bennamane N, Nedjar KB, Geronikaki AA, Eleftheriou PT, Kaoua R, Boubekeur K, Hoffman P, Chaudhary SS, Saxena AK (2011) N-substituted [phenyl-pyrazolo]- oxazin-2-thiones as COX-LOX inhibitors: influence of the replacement of the oxo group with thioxo group on the COX inhibition activity of N-substituted pyrazolo-oxazin-2-ones. ARKIVOC (ii):69-82
3. Brogden RN, Heel RC, Pakes GE, Speight TM, Avery GS (1980) Diclofenac sodium: a review of its pharmacological properties and therapeutic use in rheumatic diseases and pain of varying origin. Drugs 20:24-48
4. Dureja H, Kumar V, Gupta S, Madan AK (2007) Topochemical models for the prediction of lipophilicity of 1,3-disubstituted propan-2-one analogs. J Theor Comput Chem 6:435-448
5. Geronikaki A, Eleftheriou P, Vicini P, Alam I, Dixit A, Saxena AK (2007) 2-Thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones as new agents with SHP-2 inhibitory action. J Med Chem 51:5221-5228
6. Glide, Version 5.6 (2010) Schrodinger. LLC, New York
7. Hosni HM, Abdulla MM (2008) Anti-inflammatory and analgesic activities of some newly synthesized pyridinedicarbonitrile benzopyranopyridine derivatives. Acta Pharm 58:175-186
8. Joseph S, Sabulal B, Goerge V, Smina P, Janardhana KK (2009) Antioxidative and antiinflammatory activities of the chloroform extract of Ganoderma Scientia lucidum found in south India. Pharmaceutica 77:111-121
9. Kumar A, Rajput CS, Bhati SK (2007) Synthesis of 3-[4′-(p- chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)- aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. Bioorg Med Chem 15:3089-3096
10. Lagorce JF, Comby F, Rousseau A, Buxeraud J, Raby C (1993) Synthesis and antithyroid activity of pyridine, pyrimidine and pyrazine derivatives of thiazole-2-thiol and 2-thiazoline-2-thiol. Chem Pharm Bull 41:1258-1260
11. Lamas MC, Leonardi D, Lambri OA, Bassani G, Barrera MG, Bolmaro RE, Salomon CJ (2010) Preparation, characterization and dissolution studies of fast release diclofenac sodium tablets from PVP solid dispersions 15:162-168
12. LigPrep, Version 2.4 (2010) Schrodinger. LLC, New York
13. MacroModel, Version 9.8 (2010) Schrodinger. LLC, New York
14. Marson CM (2011) New and unusual scaffolds in medicinal chemistry. Chem Soc Rev 40:5514-5533
15. Muegge I, Oloff S (2006) Advances in virtual screening. Drug Discov Today 3:405-411
16. Murugesan V, Prabhakar YS, Katti SB (2009) CoMFA and CoMSIA studies on thiazolidin-4-one as anti-HIV-1 agents. J Mol Graph Mod 27:735-743
17. Nikolic S, Trinajstic N, Baucic I (1998) Comparison between the vertex- and edge-connectivity indices for benzenoid hydrocarbons. J Chem Inf Comput Sci 38:42-46
18. Raghubir R, Verma R, Samuel SS, Raza S, Haq W, Katti SB (2011) Anti-stroke profile of thiazolidin-4-one derivatives in focal cerebral ischemia model in rat. Chem Biol Drug Des 78:445-453
19. Rajanarendar E, Reddy ASR, Reddy KG, Raju S (2011) Synthesis and antimicrobial activity of novel spiro-isoxazolyl oxazolidin-4-one-[5,51]-1,2,4- oxadiazolines and thiazolidin-4-one-[5,51]-1,2,4-oxadiazolines. Ind J Chem 50B:1800-1806
20. Ramadan AA (2012) Preparation, characterization and in vivo evaluation of double-phased mucoadhesive suppositories containing diclofenac in rats. J App Sci Res 8:746-752
21. Ramesh D, Chandershekhar C, Vaidya VP (2008) Synthesis of novel naphtha [2,1-b]furo[3,2-b]pyridine derivatives as potential antimicrobial agents. Ind J Chem 47B:753-758
22. Rawal RK, Prabhakar YS, Katti SB, Clercq ED (2005) 2-(Aryl)-3-furan-2- ylmethyl-thiazolidin-4-ones as selective HIV-RT inhibitors. Bioorg Med Chem 13:6771-6776
23. Rawal RK, Tripathi R, Katti SB, Pannecouque C, Clercq ED (2007) Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents. Bioorg Med Chem 15:3134-3142
24. Schneider G, Fechner U (2005) Computer-based de novo design of drug-like molecules. Nat Rev Drug Discov 8:649-663
25. Sharma V, Pathak D, Kumar P (2010) Biological importance of indole nucleus in recent years: a comprehensive review. J Heterocycl Chem 47:491-502
26. Sharma A, Kumar V, Jain S, Sharma PC (2011) Thiazolidin-4-one and hydrazone derivatives of capric acid as possible anti-inflammatory, analgesic and hydrogen peroxide-scavenging agents. J Enzym Inhib Med Chem 26:546-552
27. Siddiqui N, Arshad MF, Khan SA, Ahsan W (2010) Sulfonamide derivatives of thiazolidin-4-ones with anticonvulsant activity against two seizure models: synthesis and pharmacological evaluation. J Enzym Inhib Med Chem 25:485-491
28. Still WC, Tempczyk A, Hawley RC, Hendrickson T (1990) Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 112:6127-6129
29. Varshika E, Prabhakar K, Kishan V (2009) Preparation, characterization, and in vivo pharmacodynamic evaluation of parenteral diclofenac submicron lipid emulsions. PDA J Pharm Sci Technol 63:380-389
30. Willet P (2006) Similarity-based virtual screening using 2D fingerprints. Drug Discov Today 11:1046-1053
31. Wold S (1991) Validation of QSAR's. Quant Struct Act Relatsh 10:191-193
32. Zacher J, Altman R, Bellamy N, Brühlmann P, Da Silva J, Huskisson E, Taylor RS (2008) Topical diclofenac and its role in pain and inflammation: an evidence-based review. Curr Med Res Opin 24:925-950