Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and antibacterial activity of some new 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Abstract

An efficient, synthesis of some new 1-aroyl-3-(substituted-2-benzothiazolyl)-thioureas is reported. Substituted anilines were treated with potassium thiocyanate and bromine in acidic medium to afford the corresponding 2-amino-benzothiazoles (2a–e). Treatment of the latter with suitably substituted aroyl isocyanates, produced in situ by reaction of corresponding aroyl chlorides with thiocyanate in acetone, afforded the 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas (3a–k). The structures were confirmed by physical, IR, NMR, and mass spectral data. The synthesized compounds (2a–d, 3a–k) were assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and were found to exhibit moderate to potent activity towards the tested microorganisms, as compared to the standard drugs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. R. S. Zeng, J. P. Zou, S. J. Zhi, et al.; Organic Lett., 61, 1657 (2003).

    Article  CAS  Google Scholar 

  2. A. Saeed, M. J. Parvez; Heterocycl. Chem., 43, 1027 (2006).

    CAS  Google Scholar 

  3. R. Lakhan and B. J. Ral; J. Chem. Eng. Data, 31, 501 (1986).

    Article  CAS  Google Scholar 

  4. V. K. Jain and J. T. Rao; J. Inst. Chem. (India), 75, 24 (2003).

    CAS  Google Scholar 

  5. O. J. D’Cruz, T. K. Venkatachalam, F. M. Uckun, Biol Reprod., 63, 196 (2000).

    Article  PubMed  CAS  Google Scholar 

  6. A. S. Galabov, B. S. Galabov, N. A. Neykova, J. Med. Chem. 23, 1048 (1980).

    Article  PubMed  CAS  Google Scholar 

  7. (a) L. Doub, L. M. Richardson, et al., J. Am. Chem. Soc., 80, 2205 (1958). (b) A. C. Glasser, R. M. Doughty, J. Pharm. Sci., 51, 1031 (1962).

    Article  CAS  Google Scholar 

  8. (a) G. Vasilev, Z. Tomaleva, Arch. Phytopathol. Pflanzenshuts, 9, 309 (1973). (b) G. Krause; R. Franke; G. N. Vasilev, Biochem. Physiol. Pflanz., 174, 128 (1979).

    Article  CAS  Google Scholar 

  9. G. Vasilev, L. Iliev, R. Vasilev, Mekh Gerbits 187 (1971); Chem. Deistviya Abstr., 86, 5117d (1977).

  10. T. K. Venkatachalam et al., Bioorg. Med. Chem., 11, 1095 (2003).

    Article  PubMed  CAS  Google Scholar 

  11. T. K. Venkatachalam, E. A. Sudbeck, C. Mao, F. M. Uckun, Bioorg Med Chem Lett, 10, 2071 (2000).

    Article  PubMed  CAS  Google Scholar 

  12. D. V. Krylsky, K. S. Shikhaliev, A. S. Solovyev, Chem. Heterocycl. Cmpd., 37, 524 (2001).

    Article  CAS  Google Scholar 

  13. T. Kaneto, H. Kuroda, T. Ueda, J. Pharm. Soc. Jpn., 75, 298 (1955); Abstr., 56, 1776c (1956).

    Google Scholar 

  14. T. Noguchi, S. Ohkuma, S. Kosaka, Proc. 2 nd Int. Cong. Pesticide Chem., New York, 5, 263 (1972).

    CAS  Google Scholar 

  15. C. J. Pegat, K. Kinser, R. L. Stone, D. C. Delong, J. Med. Chem., 12, 1010 (1969).

    Article  Google Scholar 

  16. P. P. Dixit, V. J. Patil, et al.; Eur. J. Med. Chem., 41, 423 (2006).

    Article  PubMed  CAS  Google Scholar 

  17. Y. X. Gong, Z. Y. Wang, Z. W. Zhang, et al., Chin. J. Org. Chem., 26(3): 360 (2006); P. V. Tale, P. Shirish, P. G. Deshmukh, Heteroatom Chem., 17, 306 (2006).

    CAS  Google Scholar 

  18. H. Suter and H. Zutter, Helv. Chim. Acta, 50, 1084 (1967).

    Article  PubMed  CAS  Google Scholar 

  19. P. Jimonet, F. Audiau, M. Barreau, et al., J. Med. Chem., 42, 2828 (1999).

    Article  PubMed  CAS  Google Scholar 

  20. S. N. Sawhney, S. K. Arora, J. V. Singh, Ind. J. Chem., 16B, 605 (1978).

    CAS  Google Scholar 

  21. G. Bensimon, L. Lacomblez, V. Meininger, New Engl. J. Med., 330, 585 (1994).

    Article  PubMed  CAS  Google Scholar 

  22. G. Foscolos, G. Tsatsas, A. Champagnac, M. Pommier, Ann. Pharm. Fr., 35, 295 (1977).

    PubMed  CAS  Google Scholar 

  23. V. G. Shirke, Bobade, R. P. Bhamaria, Ind. Drugs, 27, 350 (1990).

    CAS  Google Scholar 

  24. C. J. Paget, K. Kinser, R. L. Stone, D. C. Delong, J. Med. Chem., 12, 1061 (1969).

    Google Scholar 

  25. E. F. Domino, K. R. Unna, J. Kerwin, J. Pharmacol. Exp. Ther., 105, 486 (1952).

    PubMed  CAS  Google Scholar 

  26. F. Dessi, Y. Ben-Asi, Eur. J. Pharmacol., 250, 325 (1993).

    Article  PubMed  CAS  Google Scholar 

  27. J. Benavides, J. C. Camelin, N. Mitrani, Neuropharmacology, 24, 1085 (1985).

    Article  PubMed  CAS  Google Scholar 

  28. I. Hutchinson, S. A. Jennings, B. R. Vishnuvajjala, J. Med. Chem., 45, 744 (2002).

    Article  PubMed  CAS  Google Scholar 

  29. M. A. El-Sherbeny, Arzeneim. Forsch., 50, 848 (2000).

    CAS  Google Scholar 

  30. S. N. Pandeya, D. Sriram, P. Yogeeswari, J. P. Stables, Pharmazie, 56, 875 (2001).

    PubMed  CAS  Google Scholar 

  31. P. Yogeeswari, D. Sriram, V. Saraswat, et al., Eur. J. Pharm. Sci., 20, 341 (2003).

    Article  PubMed  CAS  Google Scholar 

  32. J. R. Dimmock, R. N. Puttucode, J. M. Smith, et al., J. Med. Chem., 39, 3984 (1996).

    Article  PubMed  CAS  Google Scholar 

  33. H. P. Kaufmann, Arch. Pharm., 266, 197 (1928).

    CAS  Google Scholar 

  34. A. Saeed, M. Parvez, Cent. Eur. J. Chem., 3, 780 (2005); A. Saeed, U. Florke, Acta Cryst., E62, 2403 (2006); A. Saeed, U. Florke, Acta Cryst., E62, 2530 (2006).

    Article  CAS  Google Scholar 

  35. J. G. Cappuccino, N. Sherman, in Microbiology: a Laboratory Manual, The Benjamin / Cummings Publishing Co. California (USA), pp. 247–251

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Quaid-I-Azam University, Islamabad, 45320, Pakistan

    Aamer Saeed & Hummera Rafique

  2. Department of Microbiology, Quaid-I-Azam University, Islamabad, 45320, Pakistan

    A. Hameed & S. Rasheed

Authors
  1. Aamer Saeed
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hummera Rafique
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Hameed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Rasheed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aamer Saeed.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saeed, A., Rafique, H., Hameed, A. et al. Synthesis and antibacterial activity of some new 1-aroyl-3-(substituted-2-benzothiazolyl)thioureas. Pharm Chem J 42, 191–195 (2008). https://doi.org/10.1007/s11094-008-0094-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-008-0094-x

Keywords

Search

Navigation