Synthesis and Antimicrobial Evaluation of 2-(Substituted-phenyl)-3-(4-(4- Nitrophenyl)Thiazol-2-yl)Thiazolidin-4-One Derivatives

Author(s): Rakesh Kumar*, Shailendra Patil.

Journal Name: Current Bioactive Compounds

Volume 15 , Issue 1 , 2019

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Abstract:

Background: Diseases caused by microbial infections are very common worldwide. Although the search of innovative antimicrobial agents is the current focus for the researchers, the treatment of infectious diseases remains an important public health issue and a challenging problem in front of medicinal chemist.

Methods: A series of 2-(4-hydroxyphenyl)-3-(4-(4-nitrophenyl) thiazol-2-yl)thiazolidin-4-one derivatives (T1-T10) was designed and synthesized. All the titled compounds were evaluated for their antimicrobial potential. Antimicrobial activity was performed by tube dilution methods against Gram negative Escherichia coli MTCC 443 (E. Coli), Gram positive bacteria: Staphylococcus aureus MTCC 3160 (S. aureus) and Bacillus subtilis MTCC 441 (B. Subtilis), and fungal strains: Aspergillus niger MTCC 281 (A. niger) and Candida albicans MTCC 227 (C. albicans).

Results: Among the synthesized derivatives, compounds 2, 4 and 10 were found to be most active antimicrobial agents.

Conclusion: In conclusion, a series of 2-(phenyl)-3-(4-(phenyl)thiazol-2-yl)thiazolidin-4-ones have been designed and synthesized. All the titled compounds were evaluated for their in vitro antimicrobial activity against five representative microorganisms. The results of antimicrobial study indicated that the presence of nitro and chloro groups in aromatic ring improved antibacterial activity, whereas the presence of hydroxy group improved antifungal activity of substituted 4-thiazolidinone derivatives.

Keywords: 4-thiazolidinone, hydrazone, antimicrobial activity, methicillin-resistant, perkin elmer spectrum, chromatography.

[1]
Kumar, M.; Jain, S.; Deep, A. Syntheses and antimicrobial activities of 2, 3-disubstituted-4-thiazolidinone terivatives. Lat AM J Phar., 2011, 30(2), 388-391.
[2]
Tenover, F.C. Mechanisms of antimicrobial resistance in bacteria. Am. J. Med., 2006, 119(6)(Suppl. 1), S3-S10.
[3]
Pfeltz, R.F.; Wilkinson, B.J. The escalating challenge of vancomycin resistance in Staphylococcus aureus. Curr. Drug Targets Infect. Disord., 2004, 4(4), 273-294.
[4]
Desai, N.C.; Dodiya, A.M.; Shihora, P.N. A clubbed quinazolinone and 4-thiazolidinone as potential antimicrobial agents. Med. Chem. Res., 2012, 21(8), 1577-1586.
[5]
El-Gaby, M.S.; El-Hag Ali, G.A.; El-Maghraby, A.A.; Abd El-Rahman, M.T.; Helal, M.H. Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4′-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones. Eur. J. Med. Chem., 2009, 44(10), 4148-4152.
[6]
Deep, A.; Jain, S.; Sharma, P.C.; Mittal, S.K.; Phogat, P.; Malhotra, M. Synthesis, characterization and antimicrobial evaluation of 2,5-disubstituted-4-thiazolidinone derivatives. Arab. J. Chem., 2014, 7, 287-291.
[7]
Wu, S.; Guo, W.; Teraishi, F.; Pang, J.; Kaluarachchi, K.; Zhang, L.; Davis, J.; Dong, F.; Yan, B.; Fang, B. Anticancer activity of 5-benzylidene-2-phenylimino-1, 3-thiazolidin-4-one (BPT) analogs. Med. Chem., 2006, 2(6), 597-605.
[8]
Deep, A.; Kumar, P.; Narasimhan, B.; Ramasamy, K.; Mani, V.; Mishra, R.K.; Majeed, A.B. Synthesis, antimicrobial, anticancer evaluation of 2-(aryl)-4- thiazolidinone derivatives and their QSAR studies. Curr. Top. Med. Chem., 2015, 15(11), 990-1002.
[9]
Srivastava, T.; Gaikwad, A.K.; Haq, W.; Sinha, S.; Katti, S.B. Synthesis and biological evaluation of 4-thiazolidinone derivatives as potential antimycobacterial agents. ARKIVOC, 2005, (ii), 120-130.
[10]
Patel, R.B.; Desai, P.S.; Desai, K.R.; Chikhalia, K.H. Synthesis of pyrimidine based thiazolidinones and azetidinones: Antimicrobial and antitubercular agents. Indian J. Chem., 2006, 45B, 773-778.
[11]
Deep, A.; Jain, S.; Sharma, P.C. Synthesis and anti-inflammatory activity of some novel biphenyl-4-carboxylic acid 5-(arylidene)-2-(aryl)-4-oxothiazolidin-3-yl amides. Acta Pol. Pharm., 2010, 67(1), 63-67.
[12]
Deep, A.; Jain, S.; Sharma, P.C.; Phogat, P.; Malhotra, M. Synthesis of 2-(aryl)-5-(arylidene)-4-thiazolidinone derivatives with potential analgesic and anti-inflammatory activity. Med. Chem. Res., 2012, 21, 1652-1659.
[13]
Ottanà, R.; Maccari, R.; Giglio, M.; Del Corso, A.; Cappiello, M.; Mura, U.; Cosconati, S.; Marinelli, L.; Novellino, E.; Sartini, S.; La Motta, C.; Da Settimo, F. Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications. Eur. J. Med. Chem., 2011, 46(7), 2797-2806.
[14]
Kumar, R.; Subban, R.; Sundaram, K.; Venkatachalapthi, S.; Ali, M.S.A. Conventional and microwave assisted synthesis of 2-aminothiazoles and oxazoles and their anti cancer activity. Indo Am. J. Pharm. Res., 2015, 5(1), 555-561.
[15]
Pharmacopoeia, Pharmacopoeia of India, vol. II. Ministry of Health Department, Govt. of India, New Delhi, pp. A-88,, 1996.
[16]
Cruickshank, R.; Duguid, J.P.; Marmion, B.P.; Swain, R.H.A. The Enterobacteriaceae: Salmonella. In: Medical Microbiology, 12th ed; Churchill Livingstone: Edinburgh, London, New York, 1975; Vol. 11, pp. 403-419.


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Article Details

VOLUME: 15
ISSUE: 1
Year: 2019
Page: [114 - 119]
Pages: 6
DOI: 10.2174/1573407213666171020102638
Price: $58

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