Date of Publication: 14-Jun-2022
Antibacterial properties of new 5-substituted derivatives of rhodanine-3-propanoic acid
Author: Nidhi Arora, Varsha Devi, Vikramdeep Monga
Bacterial infections present a serious challenge to health care practitioners due to the emergence of resistance to numerous conventional antibacterial drugs. Therefore, new bacterial targets and new antimicrobials are unmet medical needs. Rhodanine derivatives have been shown to possess potent antimicrobial activity through a novel mechanism. However, their antibacterial potential has not been completely explored. Therefore, the present study series of rhodanine-3-propanoic acid derivatives possessing hydroxyl substituted benzylidene moiety at the C-5 position of the rhodanine core was synthesized through Knoevenagel condensation of rhodanine-3-propanoic acid with various hydroxyl substituted aromatic aldehydes. All the compounds were structurally characterized and evaluated in vitro for their antibacterial activity against two Gram-positive and two Gram-negative bacterial strains. Biological data showed that various synthesized derivatives exhibited potent antibacterial activity against various tested bacterial strains.
Keywords: Rhodanine, rhodanine-3-propanoic acid, synthesis, antimicrobial, antibacterial
1. Sharma M, Chaturvedi V, Manju YK, Bhatnagar S, Srivastava K, Puri SK, et al. Substituted quinolinyl chaconnes and quinolinyl pyrimidines as a new class of anti-infective agents. Eur J Med Chem 2009;44:2081-91.
2. Goossens H. Antibiotic consumption and link to resistance. Clin Microb Infect 2009;15:12-5.
3. Boucher HW, Talbot GH, Bradley JS, Edwards JE, Gilbert D, Rice LB, et al. Bad bugs, no drugs: No ESKAPE! An update from the infectious diseases society of America. Clin Infect Dis 2009;48:1-12.
4. Lesyk RB, Zimenkovsky BS. 4-Thiazolidones: Centenarian history, current status and perspectives for modern organic and medicinal chemistry. Curr Org Chem 2004;8:1547-77.
5. Jiang H, Zhang WJ, Li PH, Wang J, Dong CJ, Zhang K, et al. Synthesis and biological evaluation of novel carbazole-rhodanine conjugates as topoisomerase II inhibitors. Bioorg Med Chem Lett 2018;28:1320-3.
6. Liu J, Wu Y, Piao H, Zhao X, Zhang W, Wang Y, et al. A comprehensive review on the biological and pharmacological activities of rhodanine based compounds for research and development of drugs. Mini Rev Med Chem 2018;18:948
. 7. Kaminskyy D, Kryshchyshyn A, Lesyk R. Recent developments with rhodanine as a scaffold for drug discovery. Expert Opin Drug Discov 2017;12:1233.
8. Krátký M, Vinšová J, Stola?íková J. Antimicrobial activity of rhodanine-3-acetic acid derivatives. Bioorg Med Chem 2017;25:1839-45.
9. Xu LL, Zheng CJ, Sun LP, Miao J, Piao HR. Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents. Eur J Med Chem 2012;48:174-8.
10. Miao J, Zheng CJ, Sun LP, Song MX, Xu LL, Piao HR. Synthesis and potential antibacterial activity of new rhodanine-3-acetic acid derivatives. Med Chem Res 2013;22:4125-32.
11. Patel BA, Ashby CR Jr., Hardej D, Talele TT. The synthesis and SAR study of phenylalanine-derived (Z)-5-arylmethylidene rhodanines as anti-methicillinresistant Staphylococcus aureus (MRSA) compounds. Bioorg Med Chem Lett 2013;23:5523-7.
12. Aneja DK, Lohan P, Arora S, Sharma C, Aneja KR, Prakash O. Synthesis of new pyrazolyl-2, 4-thiazolidinediones as antibacterial and antifungal agents. Org Med Chem Lett 2011;1:1-12.
13. Chen ZH, Zheng CJ, Sun LP, Piao HR. Synthesis of new chalcone derivatives containing a rhodanine-3-acetic acid moiety with potential anti-bacterial activity. Eur J Med Chem 2010;45:5739-43.
14. Rattan A. Antimicrobials in Laboratory Medicine. New Delhi: Churchill Livingstone; 2000. p. 85-108.