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

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.

Keywords

microwave-assisted synthesis / naphthyl / thiazolidin-4-one / antimicrobial

References

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

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

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

[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

[5] Rawal R K, Tripathi R, Katti S B, Pannecouque C, De Clercq E. Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti- HIV-1 agents. Bioorg Med Chem, 2007, 15: 3134-3142

[6] 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

[7] 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

[8] Rao A, Balzarini J, Carbone A, Chimirri A, De Clercq E, Monforte A M, Monforte 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

[9] 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

[10] 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

[11] 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

[12] 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

[13] 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

[14] 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

[15] 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

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

[17] 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

[18] 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)

[19] Zhou D Q. Experimental Microbiology Handbook. Shanghai: Shanghai Science and Technology Press, 1986

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

[21] 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)

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag Berlin Heidelberg