Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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One Pot Synthesis of Substituted [1,2,4]-Triazolo [1',2':1,2]pyrimido [6,5-b]-quinoline and Its Antibacterial Activity

  • Joshi, Ratnadeep S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mandhane, Priyanka G. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Chate, Asha V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Khan, Wajid (Department of Microbiology, Maulana Azad College) ;
  • Gill, Charansingh H. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Received : 2010.03.02
  • Accepted : 2010.06.30
  • Published : 2010.08.20
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Abstract

A convenient synthesis of substituted [1,2,4]-triazolo [1',2':1,2]pyrimido[6,5-b]-quinoline 4(a-i) from substituted 2-chloroquinoline-3-carbaldehyde 1(a-i) and 4H-1,2,4-triazol-3-amine 2 by using $SiO_2/K_2CO_3$ under microwave irradiation. This method affords the [1,2,4]-Triazolo [1',2':1,2]pyrimido[6,5-b]-quinoline 4(a-i) under the influence of microwave irradiation in solvent-free conditions within short span (12 - 20 min), & gaves excellent yields (89 - 95%). All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against control drugs.

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References

  1. Chen, Y. L.; Fang, K. C.; SheuHsu, J. Y.; Tzeng, S. L. J. Med. Chem. 2001, 44, 2374. https://doi.org/10.1021/jm0100335
  2. Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021. https://doi.org/10.1016/S0223-5234(00)01175-2
  3. Doube, D.; Blouin, M.; Brideau, M. C.; Chan, C.; Desmarais, S.; Eithier, D.; Agueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Tagari, P.; Young, R. N. Bio. & Med. Chem. Letts. 1998, 8, 1255. https://doi.org/10.1016/S0960-894X(98)00201-7
  4. Larsen, R. D.; Corley, E. G.; King, A. O.; Carrol, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. J. Org. Chem. 1996, 61, 3398. https://doi.org/10.1021/jo952103j
  5. Bringmann, G.; Reichert, Y.; Kane, V. Tetrahedron 2004, 60, 3539. https://doi.org/10.1016/j.tet.2004.02.060
  6. Ko, T. C.; Hour, M. J.; Lien, J. C.; Teng, C. M.; Lee, K. H.; Kuo, S. C.; Huang, L. J. Bioorg. & Med. Chem. Letts. 2001, 11, 279. https://doi.org/10.1016/S0960-894X(00)00652-1
  7. Ferrarini, P. L.; Mori, C.; Badwneh, M.; Manera, C.; Martinelli, A.; Miceli, M.; Ramagnoli, F.; Saccomanni, G. J. Hetero. Chem. 1997, 34, 1501. https://doi.org/10.1002/jhet.5570340520
  8. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129. https://doi.org/10.1021/jm00040a003
  9. Bolognese, A.; Correale, G.; Manfra, M.; Sposito, A.; Novellino, E.; Lavecchi, A. J. Med. Chem. 2008, 51, 8148. https://doi.org/10.1021/jm8007689
  10. Baraldi, P. G.; Tabrizi, M. A.; Preti, D.; Bovero, A.; Fruttarolo, F.; Romagnoli, R.; Zaid, N. Al.; Moorman, A. R.; Varani, K.; Borea, P. A. J. Med. Chem. 2005, 48, 5001. https://doi.org/10.1021/jm050125k
  11. Gopal, M.; Shahabuddin, M. S.; Inamdar, S. R. Proc. Ind. Acad. Sci. (Chem. Sci.) 2002, 114(6), 687. https://doi.org/10.1007/BF02708861
  12. Dominguez, J.; Lobo, D. G. Eur. J. Med. Chem. 2001, 36, 555. https://doi.org/10.1016/S0223-5234(01)01245-4
  13. Dominguez, J.; Basante, W.; Charris, J.; Riggione, F. Farmaco 1996, 51, 407.
  14. Patel, R.; Desai, K.; Chikhalia, K. J. Ind. Chem. Soc. 2003, 80, 38.
  15. Birendra, N. G.; Jiban, C. S. K.; Jogendra, N. B. J. Hetero. Chem. 1984, 21, 1225. https://doi.org/10.1002/jhet.5570210460
  16. Kothari, P. J.; Mehlhoff, M. A.; Singh, S. P.; Parmar, S. S.; Stenberg, V. I. J. Hetero. Chem. 17, 1369. https://doi.org/10.1002/jhet.5570170703
  17. Kothari, P. J.; Singh, S. P.; Parmar S. S.; Stenberg, V. I. J. Hetero. Chem. 1980, 17, 1393. https://doi.org/10.1002/jhet.5570170709
  18. Sengupta, A. K.; Misra, H. K. Ind. Chem. Soc. 1981, 8, 508.
  19. Sarmah, S. C.; Bahel, S. C. J. Ind. Chem., Soc. 1982, 59, 877.
  20. Yanborisova, O. A.; Kolla, V. I.; Vikhareva, S. A. Dep. VINTI 1990, 13, 3119.
  21. Yanborisova, O, A.; Kolla, V. I.; Vikhareva, S. A. Kl him-Farm. Zh. 1991, 25(2), 24.
  22. Yanborisova, O. A.; Kon'shina, T. M.; Zaks, A. S. Khim-Farm. Zh. 1996, 30(3), 52.
  23. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025. https://doi.org/10.1021/cr940089p
  24. Smith, K., Ed., Solid Supports and Catalysts in Organic Synthesis; Ellis Horwood and PTR Prentice Hall: New York, 1992.
  25. Villemin, D.; Vlieghe, X. Sul. Letts. 1998, 21, 191.
  26. Laszlo, P. Preparative Chemistry Using Supported Reagents; Academic Press: 1987.
  27. Dewan, S. K.; Varma, U.; Malik, S. D. J. Chem. Res. (S) 1995, 21.
  28. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boulett, F.; JacKqualt, P.; Maine, D. D. Synthesis 1998, 1, 213.t: ks
  29. Petrov, K. A.; Chauzov, V. A.; Erokhina. Usp. Khim. 1974, 43, 2045.
  30. Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus; Elsevier: Amsterdam, 1967.
  31. Atmani, A.; Combret, J. C.; Malhiac, C.; Kajima, M. J. Tett. Letts. 2000, 41, 6045. https://doi.org/10.1016/S0040-4039(00)00922-9
  32. Clark, J. H. Acc. Chem. Res. 2002, 35, 791. https://doi.org/10.1021/ar010072a
  33. Miyazaki, T.; Tokubuchi, N.; Inoue, M.; Arita, M.; Mochida, I. Energy & Fuels 1998, 12, 870. https://doi.org/10.1021/ef970213i
  34. Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H.; Bioorg. & Med. Chem. Letts. 2008, 18, 4678. https://doi.org/10.1016/j.bmcl.2008.07.007
  35. Jadhav, G. R.; Shaikh, M. U.; Shingare, M. S.; Gill, C. H. J. Het. Chem. 2008, 45(1), 1287. https://doi.org/10.1002/jhet.5570450505
  36. Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Ghawalkar, A. R.; Nagargoje, D. R.; Shiradkar, M.; Gill. C. H. Bioorg. & Med. Chem. Letts. 2008, 16, 6244.
  37. Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Shiradkar, M.; Gill, C. H. Eur. J. Med. Chem. 2009, 44(9), 2930. https://doi.org/10.1016/j.ejmech.2008.12.001
  38. Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Gill, C. H. Ultrason. Sonochem. 2010, 17, 298. https://doi.org/10.1016/j.ultsonch.2009.08.015
  39. Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H. Tett. Letts. 2010, 51, 1490. https://doi.org/10.1016/j.tetlet.2010.01.031
  40. Kale, R. P.; Jadhav, G. R.; Shaikh, M. U.; Gill, C. H. Tett. Letts. 2009, 50, 1780. https://doi.org/10.1016/j.tetlet.2008.12.104
  41. Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Gill, C. H. Chin. Chem. Letts. 2009, 20(5), 535. https://doi.org/10.1016/j.cclet.2008.12.004
  42. Srivastava, A.; Singh, R. M. Ind. J. Chem. 2005, 44(B), 1868. https://doi.org/10.1021/ie049226r

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