Effect of chloro and fluoro groups on the antimicrobial activity of 2,5-disubstituted 4-thiazolidinones: A comparative study

Medicinal Chemistry Research

Volumn 21, Issue 10, 2012, Pages 3263-3271

  Chawla, Pooja ^a   Singh, Ranjit ^b   Saraf, Shailendra K ^c  

^a BABU BANARASI DAS NATIONAL INSTITUTE OF TECHNOLOGY AND MANAGEMENT   (India)

^b SHOBHIT UNIVERSITY   (India)

^c Northern India Engineering College   (India)

Author keywords

4 Thiazolidinones; Antimicrobial; Arylidene; Imino; Knoevenagel condensation; Spectral analysis

Indexed keywords

2 (3 CHLORO 4 FLUOROPHENYLIMINO 5 ARYLIDENE 4 THIAZOLIDINONE); 2 (3 CHLORO 4 FLUOROPHENYLIMINO) 5 (2 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLORO 4 FLUOROPHENYLIMINO) 5 (3 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLORO 4 FLUOROPHENYLIMINO) 5 (4 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLORO 4 FLUOROPHENYLIMINO) 5 (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLORO 4 FLUOROPHENYLIMINO) 5 (4 HYDROXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLORO 4 FLUOROPHENYLIMINO) THIAZOLIDIN 4 ONE; 2 (3 CHLOROPHENYLIMINO 5 ARYLIDENE 4 THIAZOLIDINONE); 2 (3 CHLOROPHENYLIMINO) 5 (2 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) 5 (2 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) 5 (3 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) 5 (4 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) 5 (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) 5 (4 HYDROXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (3 CHLOROPHENYLIMINO) THIAZOLIDIN 4 ONE; 2 (4 CHLOROPHENYLIMINO 5 ARYLIDENE 4 THIAZOLIDINONE); 2 (4 CHLOROPHENYLIMINO) 5 (2 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) 5 (2 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) 5 (3 NITROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) 5 (4 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) 5 (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) 5 (4 HYDROXYBENZYLIDENE) 4 THIAZOLIDINONE; 2 (4 CHLOROPHENYLIMINO) THIAZOLIDIN 4 ONE; 2 [3 CHLORO 4 FLUOROPHENYLIMINO 5 (2 CHLOROBENZYLIDENE) 4 THIAZOLIDINONE]; 4 THIAZOLIDINONE DERIVATIVE; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ALBICANS; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG SYNTHESIS; ESCHERICHIA COLI; KNOEVENAGEL CONDENSATION; NONHUMAN; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84866405772     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9864-1     Document Type: Article

References (30)

1. Biological Assay, Indian Pharmacopoeia (1996) Govt. of India, Delhi. 2: A100-102
2. Bonde CG, Gaikwad NJ (2004) Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg Med Chem 12:2151-2161
3. Bondock S, Khalifa W, Fadda AA (2006) Utility of 1-chloro-3, 4-dihydronaphthalene-2-carboxaldehyde in the synthesis of novel heterocycles with pharmaceutical interest. Synth Commun 36:1601-1612
4. 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
5. Bruno G, Costantino L, Curinga V, Maccari R, Monforte F, Nicolo F, Ottana R, Vigorita MG (2002) Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg Med Chem 10:1077-1084
6. Chavan AA, Rai NR (2007) Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinones. Arkivoc xvi:148-155
7. Chawla P, Singh R, Saraf SK (2011) Syntheses and evaluation of 2, 5-disubstituted 4-thiazolidinone analogues as antimicrobial agents Med Chem Res. doi:10.1007/s00044-011-9730-1
8. Chugh TD (2008) Emerging and re-emerging bacterial diseases in India. J Biosci 33:549-555
9. Faidallah HM, Khan KA, Asiri AM (2011) Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents. J Flourine Chem 132:131-137
10. Fries DS (2008) Opioid Analgesics. In: Lemke LT, Williams DA, Roche VF, Zito SN (eds) Foye's principles of medicinal chemistry, 6th edn. Wolter Kluver (India) Pvt. Ltd., New Delhi, pp 652-678
11. Hara A, Suzuki T, Hashizume H, Shishido N, Nakamura M, Ushikube F, Abiko Y (1999) Effects of CP-060S, a novel Ca2? channel blocker, on oxidative stress in cultured cardiac myocytes. Eur J Pharmacol 385:81-88
12. Ishida T, In Y, Inoue M, Tanaka C, Hamanaka N (1990) Conformation of (Z)-3-carboxymethyl-[(2E)-2-methyl-3-phenylpropenylidene] rhodanine (epalrestat), a potent aldose reductase inhibitor: X-ray crystallographic, energy calculational, and nuclear magnetic resonance studies. J Chem Soc Perkin Trans 2:1085-1091
13. Kato T, Ozaki T, Tamura K (1999) Novel calcium antagonists with both calcium overload inhibition and antioxidant activity. 2. Structure-activity relationships of thiazolidinone derivatives. J Med Chem 42:3134-3146
14. Kavitha CV, Basappa S, Swamy N, Mantelingu K, Doreswamy S, Sridhar MA, Prasad JS, Rangappa KS (2006) Synthesis of new bioactive venlafaxine analogs: novel thiazolidin-4-ones as antimicrobials. Bioorg Med Chem 14:2290-2299
15. Maccari R, Del Corso A, Giglio M, Moschini R, Mura U, Ottana R (2011) In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors. Bioorg Med Chem Lett 21:200-203
16. Macherey AC, Dansette PM (2003) Chemical mechanisms of toxicity: basic knowledge for designing safer drugs. In: Wermuth CG (ed) The practice of medicinal chemistry, 2nd edn. Academic Press, Woburn
17. Momose Y, Meguro K, Ikeda H, Hatanaka C, Oi S, Sohda T (1991) Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull 39:1440-1445
18. Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Sokovic M, Ciric A, Glamoclija J (2010) Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem 18:426-432
19. Ottana R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, Chiricosta G, Di Paola R, Sautebin L, Cuzzocrea SE, Vigorita MG (2005) 5-Arylidene-2-imino- 4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg Med Chem 13:4243-4252
20. Ottana R, Maccari R, Ciurleo R, Vigorita MG, Panico AM, Caedile V, Garufi F, Ronsi.svalle S (2007) Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures. Bioorg Med Chem 15:7618-7625
21. Ozaki T, Ohi N (1999) Improved synthetic methods of CP-060S, a novel cardioprotective drug. Tetrahedron 10:3963-3968
22. Prescott ML, Harley PJ, Klein AD (2007) Microbiology, 6th edn. McGraw-Hill Companies, New York, p 851
23. Rawal RK, Prabhaka YS, Katti SB, De Clercq E (2005) 2-(Aryl)-3- furan-2-ylmethyl-thiazolidin-4-ones as selective HIV-RT inhibitors. Bioorg Med Chem 13:6771-6776
24. Rawal RK, Tripathi R, Katti SB, Pannecouque C, De Clercq E (2007) Design, synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3- thiazolidin-4-ones as anti-HIV agents. Bioorg Med Chem 15: 1725-1731
25. Ronad PM, Noolvi MN, Sapkal S, Dharbhamulla S, Maddi VS (2010) Synthesis and antimicrobial activity of 7-(2-substituted phenylthiazolidinyl)-benzopyran- 2-one derivatives. Eur J Med Chem 45:85-89
26. Shingalapur RV, Hosamani KM, Keri RS, Hugar MH (2010) Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies. Eur J Med Chem 45:1753-1759
27. Vicini P, Geronikaki AA, Anastsia K, Incerti M, Zani F (2006) Synthesis and antimicrobial activity of novel 2-thiazolylimino-5- arylidene-4- thiazolidinones. Bioorg Med Chem 14:3859-3864
28. Vicini P, Geronikaki AA, Incerti M, Zani F, Dearden J, Hewitt M (2008) 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: synthesis and structure-activity relationship. Bioorg Med Chem 16:3714-3724
29. Voss ME, Carter PH, Tebben J, Scherle PA, Brown GD, Thompson LA, Xu M, Lo YC, Yang-Liu RRQ (2003) Both 5-arylidene-2- thioxodihydropyrimidine-4,6(1H,5H)- diones and 3-thioxo-2, 3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-dependent tumor necrosis factor-a antagonists. Bioorg Med Chem Lett 13:533-538
30. Williams DH (1996) The glycopeptide story: how to kill the deadly 'Superbugs'. Nat Prod Rep 13:469-477