RESEARCH ARTICLE

 

A simple, rapid and efficient one-pot protocol for the synthesis of 2-substituted benzothiazole derivatives and their antimicrobial screening

 

 

Abdul Rauf^{I, *} ; Saloni Ganga^I; Shweta Sharma^I; Maryam Zahin^II

^IDepartment of Chemistry, Aligarh Muslim University, Aligarh 2002002, India
^IIDepartment of Agricultural Microbiology, Aligarh Muslim University, Aligarh 2002002, India

 

 

---

ABSTRACT

A rapid and efficient condensation reaction of 2-aminothiophenol with various fatty acids in solvent-free conditions with or without microwave irradiation was carried out to afford the corresponding 2-substituted benzothiazole derivatives in good to excellent yields. The structures of the new products were established by elemental analyses, IR, ¹H NMR, ¹³C NMR and mass spectral data. All the title compounds were screened for their antibacterial and antifungal activity. Most of the compounds exhibited good antimicrobial activity.

Keywords: Fatty acids, 2-substituted benzothiazole, 2-aminothiophenol, antimicrobial activity, microwave irradiation

---

 

 

Full text available only in pdf format.

 

Acknowledgements

The authors are grateful to the Chairman, Department of Chemistry, Aligarh Muslim University, for providing the necessary research facilities. We wish to give special thanks to Dr Iqbal Ahmad, Department of Agricultural Microbiology, AMU for antimicrobial activity of our compounds. We are also grateful to the Sophisticated Analytical Instrumentation Facility of the Central Drug Research Institute, Lucknow, India, for recording IR, NMR and mass spectra.

 

References

1 (a) T.D. Bradshaw, S. Wrigley, D.-F. Shi, R.J. Schultz, K.D. Paull and M. F. G. Stevens, Br. J. Cancer, 1998, 77, 745-752; (b) M.S. Chua, D.-F. Shi, S. Wrigley, T.D. Bradshaw, I. Hutchinson, P.N. Shaw, D.A. Barrett, L.A. Stanley andM.F.G. Stevens, J. Med. Chem., 1999, 42, 381-392; (c) C. O. Leong, M. Gasbell, E.A. Martin, R.T. Heydon, P.B. Farmer, M.C. Bibby, P.A. Cooper, J.A. Double, T.D. Bradshaw andM.F.G. Stevens, Br. J. Cancer, 2003, 88, 470-477.         [ Links ]

2 G.P. Gunwaradana, S. Kohmoto, S.P. Gunasekera, O.J. McConnell and F.E. Koehn, J. Am. Chem. Soc., 1988, 110, 4856-4858.         [ Links ]

3 J.F. Wolfe, T.D. Greenwood and J.M. Mulheron, Expert Opinion on Therapeutic Patents, 1998, 8, 361-381.         [ Links ]

4 http://www.freepatentonline.com/5955485.html (accessed August 2007).         [ Links ]

5 C.J. Pagent, K. Kisner, R.L. Stone and D.C. Delond, J. Med. Chem., 1969, 12, 1016-1018.         [ Links ]

6 S. Wang, G. Bao, Z. Lu, P. Wu and Z. Han, J. Mater. Sci., 2000, 35, 5873-5881.         [ Links ]

7 T. Deligeorgiev, Dyes and Pigments, 1990, 12, 243-248.         [ Links ]

8 D.W Hein, R.J. Alheim and J.J. Leavitt, J. Am. Chem. Soc., 1957, 79, 427-429.         [ Links ]

9 Y. Kanaoka, T. Hamada and O. Yonemitsu, Chem. Pharm. Bull., 1970, 18, 587-590.         [ Links ]

10 D.L. Boger, J. Org. Chem, 1978, 43, 2296-2297.         [ Links ]

11 I. Hutchinson, M.G.F. Stevens and A.D. Westwell, Tetrahedron Lett., 2000, 41, 425-428.         [ Links ]

12 Y.H. So and R. DeCaire, Synth. Commun., 1998, 28, 4123-4135.         [ Links ]

13 R.J. Perry and B.D. Wilson, Organometallics, 1994, 13, 3346-3350.         [ Links ]

14 S. Rudrawar, A. Kondaskar and A.K. Chakraborti, Synthesis, 2005, 15, 2521-2526 (the work cited in this reference deals with aromatic and various short-chain aliphatic carboxylic acids).         [ Links ]

15 R.H. Tale, Org. Lett, 2002, 4, 1641-1642.         [ Links ]

16 (a) C. Gabriel, S. Gabriel, E.H. Grant, B.S.J. Halstead and D.M. Mingos, Chem. Soc. Rev., 1998, 27, 213-223; (b) A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullete, P. Jacquult and D. Mathe, Synthesis, 1998, 27, 1213-1234.         [ Links ]

17 M. Kodomari, T. Tamaru and T. Aoyama, Synth. Commun., 2004, 37, 3029-3036.         [ Links ]

18 A. Ben-Alloum, S. Bakkas and M. Soufiaoui, Tetrahedron Lett., 1997, 38, 6395-6396.         [ Links ]

19 A.K. Chakraborti, C. Selvam, G. Kaur and S. Bhagat, Synthesis, 2004, 5, 851-855.         [ Links ]

20 J. Mustafa, M.S. Ahmad, Jr., A. Rauf and S.M. Osman, J.Am. Oil. Chem. Soc., 1984, 61, 555-558.         [ Links ]

21 A. Rauf and H. Parveen, J. Oleo. Sci., 2004, 53, 279-283.         [ Links ]

22 R. Agrawal, A. Rauf and M. Ahmad, J. Am. Oil. Chem. Soc., 1989, 66, 970-971.         [ Links ]

23 M.T. Saeed, J.Mustafa, A. Raufand S.M. Osman, J.Am. Oil. Chem. Soc, 1992, 69, 481-484.         [ Links ]

24 M.T. Saeed, J.Mustafa, A. RaufandS.M. Osman, J.Am. Oil. Chem. Soc., 1992, 69, 396-397.         [ Links ]

25 M.H. Ansari, M.T. Saeed and M. Ahmad, J. Chem. Res., Synop., 1990, 126-127.         [ Links ]

26 A. Rauf and S. Ahmad, J. Chem. Res., 2005, 407-409.         [ Links ]

27 S.M. Ahmed, F. Ahmad and S.M. Osman, J. Am. Oil. Chem. Soc, 1985, 62, 1578-1580.         [ Links ]

28 A. Rauf and H. Parveen, Indian J. Chem, 2005, 44B, 1273-1276.         [ Links ]

29 F.D. Gunstone, J. Chem. Soc., 1954, 1611-1616.         [ Links ]

30 A.W. Baur, W.M.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Path., 1966, 45, 493-496.         [ Links ]

 

 

Received 30 July 2007
Revised 31 August 2007
Accepted 14 May 2008

 

 

* To whom correspondence should be addressed. E-mail: abduloafchem@gmail.com