RESEARCH ARTICLE

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

  • Hua CHEN , 1 ,
  • Yanan LI 1 ,
  • Jie BAI 1 ,
  • Lian ZHAO 1 ,
  • Xiangguo YUAN 1 ,
  • Xiaoliu LI , 1,2 ,
  • Keqiang CAO 3
Expand
  • 1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China
  • 2. Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Ministry of Education, Hebei University, Baoding,071002, China
  • 3. College of Plant Protection,Agricultural University, Baoding, Hebei 071001, China

Received date: 28 Oct 2008

Accepted date: 29 Nov 2008

Published date: 05 Jun 2009

Copyright

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg

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.

Cite this article

Hua CHEN , Yanan LI , Jie BAI , Lian ZHAO , Xiangguo YUAN , Xiaoliu LI , Keqiang CAO . Microwave-assisted synthesis and antimicrobial activities of 2-aryl-3-(naphthalene-1 or 2-yl)-1,3-thiazolidin-4-ones[J]. Frontiers of Chemical Science and Engineering, 2009 , 3(2) : 186 -191 . DOI: 10.1007/s11705-009-0004-0

Acknowledgements

The financial supports from the National Natural Science Foundation of China (Grant No. 20672027), the Natural Science Foundation of Hebei (2005000106, 2008000588), the Research Foundation of the Ministry of Education of China (206013) and the Postdoctoral Foundation of China are gratefully acknowledged.
1
Verma A, Saraf S K. 4-Thiazolidinone-a biologically active scaffold. Eur J Med Chem, 2008, 43: 897-905

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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

DOI

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)

Outlines

/