Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Some New Biologically Active Benzothiazole Derivatives Containing Benzimidazole and Imidazoline Moieties

  • Chaudhary, Manish (Analytical & Pharmaceutical Research Laboratory, Department of Chemistry, Government College Ajmer) ;
  • Pareek, Deepak (Analytical & Pharmaceutical Research Laboratory, Department of Chemistry, Government College Ajmer) ;
  • Pareek, Pawan K. (Department of Pure and Applied Chemistry, M. D. S. University) ;
  • Kant, Ravi (Hygia Institutes of Pharmaceutical Education and Research) ;
  • Ojha, Krishan G. (Department of Pure and Applied Chemistry, M. D. S. University) ;
  • Pareek, Arun (Analytical & Pharmaceutical Research Laboratory, Department of Chemistry, Government College Ajmer)
  • Received : 2010.06.30
  • Accepted : 2010.11.02
  • Published : 2011.01.20
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Abstract

Synthesis of N-(1H-benzimidazol-2-yl)-6-substituted-1,3-benzothiazol-2-amines and 6-substituted-N-(4,5-dihydro-1H-imidazol-2-yl)-1,3-benzothiazol-2-amines by the reaction of substituted 2-aminobenzothiazoles with carbon disulphide and methyl iodide followed by the reaction with o-phenylene diamine/ethylene diamine are reported. All the synthesized compounds were characterized by elemental analysis, IR spectra and $^1H$ NMR spectral studies. The potent antibacterial and entomological (antifeedant, acaricidal, contact toxicity and stomach toxicity) activities of the synthesized compounds were investigated.

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References

  1. Besson, T.; Benetau, V.; Guillard, J.; Leonce, S.; Pfeiffer, B. J. Med. Chem. 1999, 34, 1053. https://doi.org/10.1016/S0223-5234(99)00130-0
  2. Caleta, I.; Gridisa, M.; Mrovs, S. D.; Cetina, M.; Tralic, K. V.; Pavelic, K. Il Farmaco. 2004, 59, 297. https://doi.org/10.1016/j.farmac.2004.01.008
  3. Suvarna, K.; Swain, S, P.; Gandhi, A, M. Indian J. Pharm. Sci. 2007, 69(1), 46. https://doi.org/10.4103/0250-474X.32107
  4. Shastry, C. S.; Joshi, S. D.; Aravind, M. B.; Veerapur, V. P. Ind. J. Het. Chem. 2003, 13, 57.
  5. Yilidiz-Oren, I.; Yalcin, I.; Aki-Sener, E.; Ucar, Turk, N. Eur. J. Med. Chem. 2004, 39, 291. https://doi.org/10.1016/j.ejmech.2003.11.014
  6. Latrofa, A.; Franco, M.; Lopedota, A.; Rosato, A.; Carone, D.; Vitali, C. Il Farmaco. 2005, 60, 291. https://doi.org/10.1016/j.farmac.2005.01.010
  7. Kaur, H.; Kumar, S.; Singh, I.; Saxena, K. K.; Kumar, A. Digest J. Nanomaterials and Biostructures 2010, 5(1), 67.
  8. Oketani, K.; Nagakura, N.; Harada, K. T. Eur. J. Pharmacol. 2001, 422, 209. https://doi.org/10.1016/S0014-2999(01)01022-6
  9. Paramashivappa, R.; Phani, K. P.; Rao, P. V. S.; Rao, S. Bioorg. Med. Chem. Lett. 2003, 13, 657. https://doi.org/10.1016/S0960-894X(02)01006-5
  10. Nagarajan, S, R.; De, C. G. A.; Getman, D. P.; Lu, H. F.; Sikorski, J. A.; Walker, J. L. Bioorg. Med. Chem. Lett. 2003, 11, 4769. https://doi.org/10.1016/j.bmc.2003.07.001
  11. Florence, D.; Antonio, A.; Carole, D, G.; Maxime, R.; Erik, D. C.; Pierre, T. Eur. J. Med. Chem. 2004, 39, 685. https://doi.org/10.1016/j.ejmech.2004.04.006
  12. Yang, B. Q.; Yang, P. H.; Zhu, A. L. Chinese Chemical letters 2003, 14(9), 901.
  13. Saggu, J. S.; Sharma, R.; Dureja, H.; Kumar, V. J. Indian Inst. Sci. 2002, 82, 177.
  14. Ayhan, K. G.; Kus, C.; Coban, T.; Can, Eke, B. J. Enzyme Inhib. Med. Chem. 2004, 19(2), 129. https://doi.org/10.1080/1475636042000202017
  15. Tewari, A. K.; Mishra, A. Indian J. Chem. 2006, 45(B), 489.
  16. Mahajan, S. S.; Nandre, R. G. Indian J. Chem. 2006, 45(B), 1759.
  17. Le, H. T.; Lemaire, I. B.; Gilbert, A. K.; Jolicoeur, F.; Yang, L.; Leduc, N. JPET 2004, 309, 146. https://doi.org/10.1124/jpet.103.060772
  18. Rao, A.; Chimirri, A.; Ferro, S.; Monforte. A. M.; Monforte, P.; Zappala, M. ARKIVOC 2004, 147.
  19. Navarrete, V. G.; Cedillo, R.; Hernandez, C. A.; Yepez, L.; Valdez, J.; Morales. R.; Coryes, R.; Catillo, R. Bioorg. Med. Chem. Letter 2001, 11(2), 187. https://doi.org/10.1016/S0960-894X(00)00619-3
  20. Evers, D. L.; Gloria, K.; Ptak, R. G.; Emmer, B. T.; Shin, D.; Drach, J. C. Antimicrobial agents & chemotherapy 2004, 48(10), 3918. https://doi.org/10.1128/AAC.48.10.3918-3927.2004
  21. Kilcigil, G. A.; Altanlar, N. Turk. J. Chem. 2006, 30, 223.
  22. Nawrocka, W. Boll Chim. Farm. 1996, 135(1), 18.
  23. Rivara, M.; Zuliani, V.; Cocconcelli, G.; Morini, G, V.; Comini, M.; Rivara, S. Bioorg. Med. Chem. Lett. 2006, 14(5), 1413. https://doi.org/10.1016/j.bmc.2005.09.063
  24. Shaya, Y. A. R.; Ahmed, M. S.; Elsharief, Saied, M. E. K.; Abdulkhaliq, M. A. A. Heteroatom Chem. 2006, 17(7), 634. https://doi.org/10.1002/hc.20244
  25. Shaya, Y. A. R.; Ahmed, M. S.; Elsharief, Saied, M. E. K.; Abdulkhaliq, M. A. A. Chem-Inform. 2007, 38, 12.
  26. Pandey, J.; Tiwari, V. K.; Verma, S. S.; Chaturvedi, V.; Bhatnagar, S.; Sinha, S.; Gaikwad, A. N.; Tripathi, R. P. Eur. J. Med. Chem. 2009, 44, 3350 https://doi.org/10.1016/j.ejmech.2009.02.013
  27. Dahiya, R.; Kumar, A. E. J. Chem. 2008, 5, 1133. https://doi.org/10.1155/2008/161783
  28. Banfi, E.; Scialino, G.; Zampieri, D.; Mamolo, M. G.; Vio, L.; Ferrone, M.; Fermeglia, M.; Paneni, M. S.; Pricl, S. J. Antimicrob. Chemother. 2006, 58, 76. https://doi.org/10.1093/jac/dkl182
  29. Ulusoy, N.; Gursu, E.; Ozkirimil, S.; Ekinci, A. C.; Dikici, I. Indian J. Chem. 2003, 42(B), 2853. https://doi.org/10.1021/ie020787x
  30. Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; Clercq, E. D.; Balzarini, J. Eur. J. Med. Chem. 2009, 44(6), 2347. https://doi.org/10.1016/j.ejmech.2008.08.010
  31. Atia, A. J. K. Molecules 2009, 14, 2431. https://doi.org/10.3390/molecules14072431
  32. Ojha, K. G.; Jain, S. K.; Gupta, R. R. Synth. Commun. 1979, 9(6), 457. https://doi.org/10.1080/00397917908060947
  33. Gupta, R. R.; Ojha, K. G.; Kumar; M. J. Heterocycl. Chem. 1980, 17, 1325. https://doi.org/10.1002/jhet.5570170638
  34. Cruickshank, R.; Duguid, J. P.; Marmion, B. P.; Swam, H. A. The Practice of Medical Microbiology, 12th Ed.; Churchill Livingstone: London, 1975; p 544.
  35. Shelton, A. M.; Robertson, J. L.; Tang, J. D. J. Econ., Entomol. 1993, 86(9), 697. https://doi.org/10.1093/jee/86.3.697
  36. Jinfeng, H.; Pei, L.; Xueyan, S.; Xiwu, G. J. Insect. Sci. 2008, 8(3), 9.
  37. Leonardi, M. G.; Cappelloza, S.; Ianne, P.; Cappelloza, L.; Parenti, P.; Giordana, B. Compedium of Biochemistry and Physiology 1996, 113(B), 361.
  38. Ludvik, G. F. J. Econ. Entomol. 1953, 46, 364. https://doi.org/10.1093/jee/46.2.364

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