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Microwave-assisted synthesis and antimicrobial activities of 2-aryl-3-(naphthalene-1 or 2-yl)-1,3-thiazolidin-4-ones

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Abstract

2-aryl-3-(naphthalene-1 or 2-yl)-1, 3-thiazolidin-4-ones 4 and 5 were synthesized in 41%–67% yield by using microwave-assisted one-pot protocol. The structures of the new compounds 4l, 4m, 5c, 5e, 5g, 5h, and 5j–5m were confirmed by IR, NMR, MS, and elemental analysis. The antimicrobial activities of the compounds against Pseudomonas syringae pv. lachrymans (Smith et Bryan) Young, Dye & Wilkie, Botrytis cinerea Pers., and Sphaerotheca fusca Blum. were examined. Some of the compounds showed good antifungical activity against Sphaerotheca fusca Blum.

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References

  1. Verma A, Saraf S K. 4-Thiazolidinone-a biologically active scaffold. Eur J Med Chem, 2008, 43: 897–905

    Article  CAS  Google Scholar 

  2. Singh S P, Parmar S S, Raman K, Stenberg V I. Chemistry and biological activity of thiazolidinones. Chem Rev, 1981, 81: 175–203

    Article  CAS  Google Scholar 

  3. Frances C B. 4-Thiazolidinone. Chem Rev, 1961, 61: 463–521

    Article  Google Scholar 

  4. Rawal R K, Tripathi R, Katti S B, Pannecouque C, De Clercq E. Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Eur J Med Chem, 2008, 43: 2800–2806

    Article  CAS  Google Scholar 

  5. Rawal R K, Tripathi R, Katti S B, Pannecouque C, De Clercq E. Design, synthesis, and evaluation of 2-aryl-3-heteroaryl-1, 3-thiazolidin-4-ones as anti-HIV agents. Bioorg Med Chem, 2007, 15: 1725–1731

    Article  CAS  Google Scholar 

  6. Rawal R K, Prabhakar Y S, Katti S B, De Clercq E. 2-(Aryl)-3-furan-2-yl methyl-thiazolidin-4-ones as selective HIV-RT Inhibitors. Bioorg Med Chem, 2005, 13: 6771–6776

    Article  CAS  Google Scholar 

  7. Rao A, Balzarini J, Carbone A, Chimirri A, De Clercq E, Monforte A M, onforte P, Pannecouque C, Zappalà M. 2-(2,6-Dihalophenyl)-3-(pyrimidin-2-yl)-1,3-thiazolidin-4-ones as non-nucleoside HIV-1 reverse transcriptase inhibitors. Antivir Res, 2004, 63: 79–84

    Article  CAS  Google Scholar 

  8. Barreca M L, Chimirri A, De Clercq E, De Luca L, Monforte A M, Monforte P, Rao A, Zappalà M. Anti-HIV agents: design and discovery of new potent RT inhibitors. IlFarmaco, 2003, 58: 259–263

    Article  CAS  Google Scholar 

  9. Barreca M L, Balzarini J, Chimirri A, De Clercq E, De Luca L, Höltje H D, Höltje M, Monforte A M, Monforte P, Pannecouque C, Rao A, Zappalà M. Design, synthesis, structure-activity relationships, and molecular modeling studies of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents. J Med Chem, 2002, 45: 5410–5413

    Article  CAS  Google Scholar 

  10. Rao A, Carbone A, Chimirri A, De Clercq E, Monforte A M, Monforte P, Pannecouque C, Zappalà M. Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-(thi)one derivatives. IlFarmaco, 2002, 57: 747–751

    Article  CAS  Google Scholar 

  11. Barreca M L, Chimirri A, De Luca L, Monforte A M, Monforte P, Rao A, Zappalà M. Balzarini J, De Clercq E, Pannecouque C, Witvrouw M. Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents. Bioorg Med Chem Lett, 2001, 11: 1793–1796

    Article  CAS  Google Scholar 

  12. Garino C, Tomita T, Pietrancosta N, Laras Y, Rosas R, Herbette G, Maigret B, Quéléever G, Iwatsubo T, Kraus J L. Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human β-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays. J Med Chem, 2006, 49: 4275–4285

    Article  CAS  Google Scholar 

  13. Jia Z Z, Wu Y H, Huang W R, Zhang P L, Song Y H, Woolfrey J, Sinha U, Arfsten A E, Edwards S T, Hutchaleelaha A, Hollennbach S J, Lambing J L, Scarborough R M, Zhu B Y. 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 3: Design, synthesis and SAR of orally bioavailable benzamidine-P4 inhibitors. Bioorg Med Chem Lett, 2004, 14: 1229.1234

    Google Scholar 

  14. Sharma S, Singh T, Mittal R, Saxena K K, Srivastava V K, Kumar A. A study of anti-inflammatory activity of some novel α-amino naphthalene and β-amino naphthalene derivatives. Arch Pharm Chem Life Sci, 2006, 339: 145–152

    Article  CAS  Google Scholar 

  15. Matharu B K, Manraov M R, Kaul V K. Synthesis and nematicidal activity of 4-thiazolidinones. Indian J of Heterocyclic Chem, 2005, 339: 95–96

    Google Scholar 

  16. Solankee A, Patel J, Kapadia K, Thakor I, Upadhyay K. Synthesis and antimicrobial activity of some new 2-(3′-phenoxy phenyl)-3-aryl-5-methyl-4-thiazolidinones. Asian J Chem, 2002, 14: 718–722

    CAS  Google Scholar 

  17. Chen H, Bai J, Zhao L, Yuan X G, Li X L, Cao K Q. Microwave assisted synthesis and antibacterial study of 3-naphthyl-2-[(un) substituted phenyl]-1,3-thiazolidin-4-ones. Chinese J Org Chem, 2008, 28: 1092–1096 (in Chinese)

    CAS  Google Scholar 

  18. Zhou D Q. Experimental Microbiology Handbook. Shanghai: Shanghai Science and Technology Press, 1986

    Google Scholar 

  19. Zhang S H. The study of fungicidal bioassay method. Acta Scientiarum Naturalium Universitatis Nankaiensis (Natural Science Edition), 2000, 33: 37–40 (in Chinese)

    Google Scholar 

  20. Hao Y J, Wang W L, Li C Y, Wang Y. Improvement on bioassay methods of sphareotheca fuliginea. Tianjin Agricultural Sciences, 2005, 11: 37–40 (in Chinese)

    Google Scholar 

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Correspondence to Hua Chen or Xiaoliu Li.

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Chen, H., Li, Y., Bai, J. et al. Microwave-assisted synthesis and antimicrobial activities of 2-aryl-3-(naphthalene-1 or 2-yl)-1,3-thiazolidin-4-ones. Front. Chem. Eng. China 3, 186–191 (2009). https://doi.org/10.1007/s11705-009-0004-0

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