SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NOVEL 5-ARYLIDENE-2-IMINO-3-(2- PHENYL- 1,8-NAPHTHYRIDIN-3-YL)THIAZOLIDIN-4-ONES

  • RAMALINGAM KUNDENAPALLY MAHATMA GANDHI UNIVERSITY
  • RAMESH DOMALA MAHATMA GANDHI UNIVERSITY
  • SREENIVASULU BATHULA JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY

Abstract

Objectives: Nowadays, antimicrobial resistance represents one of the most significant challenges in the medical community. To overcome the problem, it requires the discovery of newer safe and effective molecules against infectious sickness. Synthesis and screening of 1,8-naphthyridines have attracted much attention over the decades since it plays a key role against the microorganisms.


Methods: 1,8-naphthyridine based 5-arylidene derivatives of thiazolidinone (3a-i) has been achieved by the cyclization reaction of 2-chloro-N- (2-phenyl-1,8-naphthyridin-3-yl)acetamide (1) with potassium thiocyanate in acetone followed by its Knoevenagel condensation reaction with appropriate arylaldehydes in ethanol. All the resulting products were confirmed using spectral and physicochemical data. Antibacterial activity was performed against different bacterial strains by agar disc diffusion method using ciprofloxacin as standard.


Results: Compound 3b showed tremendous antibacterial activity among all the tested compounds.


Conclusions: This study provides several advantages such as shorter reaction times, clean product, and good yields. Most of the final products possessed moderate to excellent antibacterial activity.

Keywords: 1,8-Naphthyridine, Thiazolidin-4-one, N-2-chloroacetamide, Knoevenagel, Antibacterial activity

References

1. Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of new 4-thiazolidinone, pyrazoline-, and isatin-based conjugates with promising antitumor activity. J Med Chem 2012;55:8630-41.
2. Litvinov VP. Chemistry and biological activities of 1,8-naphthyridines. Russ Chem Rev 2004;73:637-70.
3. Egawa H, Miyamoto T, Minamida A, Nishimura Y, Okada H, Uno H, et al. Pyridonecarboxylic acids as antibacterial agents 4. Synthesis and antibacterial activity of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4 -dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and its analogues. J Med Chem 1984;27:1543-8.
4. Mahesh R, Dhar AK, Jindal A, Bhatt S. Design, synthesis and evaluation of antidepressant activity of novel 2-methoxy 1, 8 naphthyridine 3-carboxamides as 5-HT3 receptor antagonists. Chem Biol Drug Des 2014;83:583-91.
5. Badawneh M, Aljamal J. Synthesis and antitubercular activity of piperidine and morpholine 1,8-Naphthyridine analogues. Int J Pharm Pharm Sci 2016;8:252-7.
6. Atanasova M, Ilieva S, Galabov B. QSAR analysis of 1,4-dihydro-4- oxo-1-(2-thiazolyl)-1,8-naphthyridines with anticancer activity. Eur J Med Chem 2007;42:1184-92.
7. Badawneh M, Ferrarini PL, Calderone V, Manera C, Martinotti E, Mori C, et al. Synthesis and evaluation of antihypertensive activity of 1,8-naphthyridine derivatives. Part X. Eur J Med Chem 2001;36:925-34.
8. Ferrarini PL, Badawneh M, Franconi F, Manera C, Miceli M, Mori C, et al. Synthesis and antiplatelet activity of some 2,7-di(N-cycloamino)- 3-phenyl-1,8-naphthyridine derivatives. Farmaco 2001;56:311-8.
9. Mulwad VV, Mir AA, Parmar HT. Synthesis and antimicrobial screening of 5-benzylidene-2-imino-3-(2-oxo-2H-benzopyran-6- yl)- thiazolidine-4-one and its derivatives. Ind J Chem 2009;48:137-41.
10. Ottanà R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, et al. 5-Arylidene-2-imino-4-thiazolidinones: Design and synthesis of novel anti-inflammatory agents. Bioorg Med Chem 2005;13:4243-52.
11. Abo-Salem HM, Ebaid MS, El-Sawy ER, El-Gendy AE, Mandour AH. Synthesis and DPPH radical-scavenging activity of some new 5-(N-substituted-1H-indol-3-yl)-5H-thiazolo[4,3-b]-1,3,4-thiadiazole derivatives. Egypt Pharm J 2013;12:11-9.
12. Liu HL, Lieberzeit Z, Anthonsen T. Synthesis and fungicidal activity of 2-imino-3-(4-arylthiazoly-2-yl)-thiazolidinones and their 5-arylidine derivatives. Molecules 2000;5:1055-61.
13. Eman SN, Salwa ME, Eman RZ. Synthesis, anticancer evaluation and molecular modeling of some substituted thiazolidinonyl and thiazolyl pyrazole derivatives. Int J Pharm Pharm Sci 2015;7:353-9.
14. Gursoy A, Terzioglu N. Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turk J Chem 2005;29:247-54.
15. Lakhan R, Singh RL. The synthesis and evaluation of 2-imino-3-(4- arylthiazol-2-yl)-4-thiazolidinones and their 5-arylidene derivatives as potential agricultural fungicides. Proc Indian Acad Sci Chem Sci 1991;103:33-41.
16. Saravanan G, Selvaraju R, Nagarajan S. Synthesis of novel 2-iminothiazolidin-4-ones. Syn comm 2012;42:3361-7.
17. Ramalingam K, Ramesh D, Sreenivasulu B. Regioselective synthesis of novel [N-(4-oxo-3-(2-phenyl-1,8-naphthyridin-3-yl)-thiazolidin-2- ylidene)]acetamide benzamides and their biological activity. Asian J Chem 2019;31:1246-50.
18. Ramalingam K, Ramesh D, Sreenivasulu B. Synthesis of 2-[(5-aryl- 1,3,4-oxadiazol-2-yl)thio]-N-(2-phenyl-1,8-naphthyridin-3-yl) acetamide and 2-[substituted-(1H-benzo[d]imidazol-2-yl)thio]-N-(2- phenyl-1,8-naphthyridin-3-yl)acetamide derivatives as antibacterial agents. Rasayan J Chem 2019;12:583-8.
19. Momose Y, Meguro K, Ikeda H, Hatanaka C, Oi S, Sohda T, et al. Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull (Tokyo) 1991;39:1440-5.
20. Hosseinzadeh N, Hasani M, Foroumadi A, Nadri H, Emami S, Samadi N, et al. 5-Nitro-heteroarylidene analogs of 2-thiazolylimino- 4-thiazolidinones as a novel series of antibacterial agents. Med Chem Res 2013;22:2293-302.
21. Benson HJ. Microbiological Applications. 5th ed. Boston, USA: W.C. Brown Publications; 1990. p. 134.
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KUNDENAPALLY, R., R. DOMALA, and S. BATHULA. “SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NOVEL 5-ARYLIDENE-2-IMINO-3-(2- PHENYL- 1,8-NAPHTHYRIDIN-3-YL)THIAZOLIDIN-4-ONES”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 12, no. 8, June 2019, pp. 150-3, https://innovareacademics.in/journals/index.php/ajpcr/article/view/34273.
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