RESEARCH ARTICLE

 

Synthesis, characterization and antimicrobial studies of some novel 1,3,4-thiadiazolium-2-thiolate derivatives

 

 

Shahrukh T. Asundaria; Shreyas A. Patel; Kalpesh M. Mehta; Keshav C. Patel^*

Department of Chemistry, Veer Narmad South Gujarat University, Udhana-Magdalla Road, Surat, 395007 (Gujarat) India

 

 

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ABSTRACT

In this study, ten new 5-substituted-3-[4,6-di(morpholine-4-yl)-1,3,5-triazine-2-yl]-1,3,5-thiadiazolium-2-thiolate 6(a-j) were prepared via a five step procedure from the starting material 1,3,5-triazine (1). Structures of all synthesized compounds were confirmed by spectral data and elemental analyses. Newly synthesized compounds were tested for their antibacterial and antifungal activities against some important bacterial and fungal species. Some of the compounds were found to be moderately active against the tested organisms.

Keywords: Thiadiazol, s-triazine, mesoionic, NMR spectroscopy, IR spectroscopy

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Full text available only in PDF format.

 

Acknowledgements

The authors are thankful to Atul Limited, Valsad and Ami Organics, Sachin, for providing some useful chemicals.

 

References

1 R.F. Rodrigues, E.F. da Silva, Á. Echevarria, R. Fajardo-Bonin, VF. Amaral, L.L. Leon, M.M. Canto-Cavalheiro, Eur. J. Med. Chem., 2007, 42, 1039-1043.         [ Links ]

2 S.A. de Morais, C.R. da Silva Morais, P.F. de Athayde Filho, B.F. Lira, R.S.T. Rocha do Nascimento, J. Therm. Anal. Colorim., 2009, 97, 437-441.         [ Links ]

3 W. Kozminski, J. Jazwinski, L. Stefaniak, G.A. Webb, Magnet. Reson. Chem., 1994, 32, 746-748.         [ Links ]

4 B.F. Lira, P.F. de Athayde Filho, J. Miller, A.M. Simas, A. de Farias Dias, M.J. Vieira, Molecules, 2002, 7, 791-800.         [ Links ]

5 A. Shuki, M. Jiro, A. Naomitsu, B. Yasuo, J. Chem. Soc., Perkin. Trans. I, 1995, 1989-1991.         [ Links ]

6 J.C. Cardoso, S.M.S.C. Cadena, A. Zampronio, A.M.S. Arruda, E.G.S. Carnieri, A. Echevarria, J. Constantin, A. Bracht, M.B.M. Oliveira, Drug Develop. Res., 2004, 61, 207-217.         [ Links ]

7 P.Z. Hu, J.G. Wang, L.F. Ma, B.T. Zhao, L.Y. Wang, Acta. Cryst., 2006, E62, o350-o351.         [ Links ]

8 A. Senff-Ribeiro, A. Echevarria, E.F. Silva, C.R. C. Franco, S.S. Veiga, M.B.M. Oliveira, British J. Cancer, 2004, 91, 297-304.         [ Links ]

9 P.F. de Athayde Filho, B.P. Howe, J. Miller, Met. Based Drugs, 2000, 7, 55-55.         [ Links ]

10 J.C. Kappel, T.S. Yokum, G. Barany, J. Comb. Chem, 2004, 6, 746-752.         [ Links ]

11 T.G. Stewart, L.B. Kier, J. Pharm. Sci., 1965, 54, 731-734.         [ Links ]

12 L.B. Kier, M.C. Dodda, P. Sapko, T.G. Stewart, Nature, 1964, 204, 697-697.         [ Links ]

13 A. Senff-Ribeiro, A. Echevarria, E.F. Silva, S.S. Veiga, M.B.M. Oliveira, Anti-cancer Drugs, 2004, 15, 269-275.         [ Links ]

14 A. Kumar, S.K. Menon, Eur. J. Med. Chem., 2009, 44, 2178-2183.         [ Links ]

15 C. Zhou, J. Min, Z. Liu, A. Young, H. Desharzer, T. Gao, Y. Chang, N. Kallenbach., Bioorg. Med. Chem. Lett., 2008, 18, 1308-1311.         [ Links ]

16 X. Sun, Z. Cao, Y. Sun, Indus. Eng. Chem. Res., 2009, 48, 607-612.         [ Links ]

17 K. Srinivas, U. Srinivas, VJ. Rao, K. Bhanuprakash, K. Harikishor and U.S.N. Murthy, Bioorg. Med. Chem. Lett., 2005, 15, 1121-1123.         [ Links ]

18 D.H. Patel, K.H. Chikhalia, N.K. Shah, D.P. Patel, P.B. Kaswala, VM. Buha, J. Enz. Inhib. Med. Chem, 2010, 25, 121-125.         [ Links ]

19 A.V. Aksenov, I.V Aksenova, Chem. Heterocyclic Comp., 2009, 45, 130-150.         [ Links ]

20 N. Nishimura, A. Kato, Carbohyd. Res, 2001, 331, 77-82.         [ Links ]

21 B. Klenke, M. Stewart, M.P. Barrett, R. Brun, I.H. Gilbert, J. Med. Chem., 2001, 44, 3440-3452.         [ Links ]

22 N.C. Desai, J.J. Bhatt, B.R. Shah, P.B. Trivedi, N.K. Undavia, Indian J. Exp. Biol., 1996, 34, 584-587.         [ Links ]

23 S. Manohar, S.I. Khan, D.S. Rawat, Bioorg. Med. Chem. Lett., 2010, 20, 322-325.         [ Links ]

24 S.B. Katiyar, K. Srivastava, S.K. Puri, P.M.S. Chauhan, Bioorg. Med. Chem. Lett., 2005, 15, 4957-4960.         [ Links ]

25 Z. Nie, C. Perretta, P. Erickson, S. Margosiak, J. Lu, A. Averill, K.M. Yager, S. Chu., Bioorg. Med. Chem. Lett., 2007, 17, 4191-4195.         [ Links ]

26 Z. Nie, C. Perretta, P. Erickson, S. Margosiak, J. Lu, A. Averill, R. Almassy, S. Chu., Bioorg. Med. Chem. Lett., 2008, 18, 619-623.         [ Links ]

27 J.J. Jogul, B.V. Badami, J. Serb. Chem. Soc, 2006, 71, 851-860.         [ Links ]

28 G. Marcotrigiano, R. Battistuzzi, G.C. Pellacani, Can. J. Chem., 1972, 50, 2557-2560.         [ Links ]

29 T.T. Nguyen, Clays Clay Min., 1986, 34, 521-528.         [ Links ]

30 K.C. Patel, S.T. Asundaria, P.R. Patel, Int. J. Polym. Mat., 2010, 59, 118-133.         [ Links ]

31 H. Bader, E.R. Ruckel, F.X. Markley, C.G. Santangelo, P. Schickedantz, J. Org. Chem., 1965,30, 702-707.         [ Links ]

32 M.M. Tarpay, D.F. Welch, M.I. Marks, Antimicrob. Agents Chemo., 1980, 18, 579-581.         [ Links ]

33 C.A.G.N. Montalbetti, T.S. Coulter, M.K. Uddin, S.G. Reignier, F. Magaraci, C. Granas, C. Krog-Jensen, J. Felding, Tetrahedron Lett., 2006, 47, 5973-5975.         [ Links ]

34 F. Karci, N. Ertan, Dyes Pigments, 2002, 55, 99-108.         [ Links ]

 

 

Received 3 June 2010
Revised 12 July 2010
Accepted 2 September 2010

 

 

* To whom correspondence should be addressed. E-mail: drkeshavpatel@rediffmail.com and shahrukh_sun@rediffmail.com