Research Reviews

Antitubercular drugs: advances in nitrogen containing heterocyclic compounds and some other derivatives

987 Views316 Downloads4 Citations

PDF

Abstract

Tuberculosis (TB) caused by Mycobacterium tuberculosis is an infectious disease. Control of TB is complicated by difficulties in the long-course chemotherapy treatment, the inability to eliminate latent microbes, and the increasing emergence of Multidrug Resistant (MDR) strains of M. tuberculosis. New anti-TB drugs are urgently needed, including developments of short-term treatments to minimize the emergence of drug resistance and new drugs to treat multidrug resistant tuberculosis and to eliminate the latent microbes. Many new structural anti-TB agents exhibited promising activities against susceptible and resistant strains of M. tuberculosis. The diarylquinoline with superior anti-tuberculotic activity and encouraging results of nitroimidazopyrans and oxazolidinones have generated considerable excitement.

References

  1. Asif, M., Study of clinically used and recently developed antimycobacterial agents. Orient Pharm Exp Med 2012, 12, 15-34.
  2. http://dx.doi.org/10.1007/s13596-011-0020-8 DOI: https://doi.org/10.1007/s13596-011-0020-8
  3. Zhang, Y.; Post-Martens, K.; Denkin, S., New drug candidates and therapeutic targets for tuberculosis therapy. Drug Discov Today 2006, 11, 21-27.
  4. http://dx.doi.org/10.1016/S1359-6446(05)03626-3 DOI: https://doi.org/10.1016/S1359-6446(05)03626-3
  5. Hasan, S.; Daugelat, S.; Rao, P. S.; Schreiber, M., Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. PLoS Comput Biol 2006, 2, e61.
  6. http://dx.doi.org/10.1371/journal.pcbi.0020061 DOI: https://doi.org/10.1371/journal.pcbi.0020061
  7. Zhang, Y., Persistent and dormant tubercle bacilli and latent tuberculosis. Front Biosci 2004, 9, 1136-1156.
  8. http://dx.doi.org/10.2741/1291 DOI: https://doi.org/10.2741/1291
  9. Dye, C., Global epidemiology of tuberculosis. Lancet 2006, 367, 938-940.
  10. http://dx.doi.org/10.1016/S0140-6736(06)68384-0 DOI: https://doi.org/10.1016/S0140-6736(06)68384-0
  11. Asif, M., Recent Efforts for the Development of Antitubercular Drug Containing Diazine Ring. Med Chem 2012, 2, 151-167. DOI: https://doi.org/10.4172/2161-0444.1000133
  12. Blumberg, H.; Burman, W.; Chaisson, R.; Daley, C.; Etkind, S.; Friedman, L.; Fujiwara, P.; Grzemska, M.; Hopewell, P.; Iseman, M., American Thoracic Society/Centers for Disease Control and Prevention/Infectious Diseases Society of America: treatment of tuberculosis. Am J Resp Crit Care Med 2003, 167, 603.
  13. http://dx.doi.org/10.1164/rccm.167.4.603 DOI: https://doi.org/10.1164/rccm.167.4.603
  14. Asif, M., Mini review on Ethmabutol and its some analogues as antitubercular agents. Elixir Pharm 2012, 53, 11774-11778.
  15. Asif, M., Study of currently used antimycobacterials, their analogoues and recently developed agents. Indian Drugs 2012, 49, 5-19. DOI: https://doi.org/10.53879/id.49.07.p0005
  16. Zhang, Y.; Amzel, L., Tuberculosis drug targets. Curr Drug Targets 2002, 3, 131-154.
  17. http://dx.doi.org/10.2174/1389450024605391 DOI: https://doi.org/10.2174/1389450024605391
  18. Asif, M.; Siddiqui, A. A.; Husain, A., Quinolone derivatives as antitubercular drugs. Med Chem Res 2013, 22, 1029-1042.
  19. http://dx.doi.org/10.1007/s00044-012-0101-3 DOI: https://doi.org/10.1007/s00044-012-0101-3
  20. Asif, M., A review on potent antitubercular agent isoniazid and its Analogues. Int J Pharm Chem 2013, 2, 110-120.
  21. http://dx.doi.org/10.7439/ijpc.v2i4.755 DOI: https://doi.org/10.7439/ijpc.v2i4.755
  22. Eswaran, S.; Adhikari, A. V.; Ajay Kumar, R., New 1, 3-oxazolo [4, 5-c] quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties. Eur J Med Chem 2010, 45, 957-966.
  23. http://dx.doi.org/10.1016/j.ejmech.2009.11.036
  24. http://dx.doi.org/10.1016/j.ejmech.2010.04.022
  25. Eswaran, S.; Adhikari, A. V.; Chowdhury, I. H.; Pal, N. K.; Thomas, K., New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties. Eur J Med Chem 2010, 45, 3374-3383.
  26. http://dx.doi.org/10.1016/j.ejmech.2009.11.036 DOI: https://doi.org/10.1016/j.ejmech.2009.11.036
  27. http://dx.doi.org/10.1016/j.ejmech.2010.04.022 DOI: https://doi.org/10.1016/j.ejmech.2010.04.022
  28. Gonalves, R. S.; Kaiser, C. R.; Lourenco, M.; de Souza, M. V.; Wardell, J. L.; Wardell, S. M.; da Silva, A. D., Synthesis and antitubercular activity of new mefloquine-oxazolidine derivatives. Eur J Med Chem 2010, 45, 6095-6100.
  29. http://dx.doi.org/10.1016/j.ejmech.2010.09.024 DOI: https://doi.org/10.1016/j.ejmech.2010.09.024
  30. Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pak, D.; He, R.; Franzblau, S. G., Synthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs. Bioorg Med Chem Lett 2010, 20, 1263-1268.
  31. http://dx.doi.org/10.1016/j.bmcl.2009.11.105 DOI: https://doi.org/10.1016/j.bmcl.2009.11.105
  32. Kini, S. G.; Bhat, A. R.; Bryant, B.; Williamson, J. S.; Dayan, F. E., Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives. Eur J Med Chem 2009, 44, 492-500.
  33. http://dx.doi.org/10.1016/j.ejmech.2008.04.013 DOI: https://doi.org/10.1016/j.ejmech.2008.04.013
  34. Yang, C.-L.; Tseng, C.-H.; Chen, Y.-L.; Lu, C.-M.; Kao, C.-L.; Wu, M.-H.; Tzeng, C.-C., Identification of benzofuro [2, 3- b] quinoline derivatives as a new class of antituberculosis agents. Eur J Med Chem 2010, 45, 602-607.
  35. http://dx.doi.org/10.1016/j.ejmech.2009.10.050 DOI: https://doi.org/10.1016/j.ejmech.2009.10.050
  36. Wube, A. A.; Hfner, A.; Thomaschitz, C.; Blunder, M.; Kollroser, M.; Bauer, R.; Bucar, F., Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4 (1 H)-quinolones. Bioorg Med Chem 2011, 19, 567-579.
  37. http://dx.doi.org/10.1016/j.bmc.2010.10.060 DOI: https://doi.org/10.1016/j.bmc.2010.10.060
  38. De Logu, A.; Palchykovska, L. H.; Kostina, V. H.; Sanna, A.; Meleddu, R.; Chisu, L.; Alexeeva, I. V.; Shved, A. D., Novel N-aryl-and N-heteryl phenazine-1-carboxamides as potential agents for the treatment of infections sustained by drug-resistant and multidrug-resistant Mycobacterium tuberculosis. Int J Antimicrob Ag 2009, 33, 223-229.
  39. http://dx.doi.org/10.1016/j.ijantimicag.2008.09.016 DOI: https://doi.org/10.1016/j.ijantimicag.2008.09.016
  40. Vicente, E.; Prez-Silanes, S.; Lima, L. M.; Ancizu, S.; Burguete, A.; Solano, B.; Villar, R.; Aldana, I.; Monge, A., Selective activity against Mycobacterium tuberculosis of new quinoxaline 1, 4-di- N-oxides. Bioorg Med Chem 2009, 17, 385-389.
  41. http://dx.doi.org/10.1016/j.bmc.2008.10.086 DOI: https://doi.org/10.1016/j.bmc.2008.10.086
  42. Rao, S. S.; Raghunathan, R.; Ekambaram, R.; Raghunathan, M., In vitro activities of the newly synthesised ER-2 against clinical isolates of Mycobacterium tuberculosis susceptible or resistant to antituberculosis drugs. Int J Antimicrob Ag 2009, 34, 451-453.
  43. http://dx.doi.org/10.1016/j.ijantimicag.2009.06.014 DOI: https://doi.org/10.1016/j.ijantimicag.2009.06.014
  44. Turan-Zitouni, G.; zdemir, A.; Asim Kaplancikli, Z.; Benkli, K.; Chevallet, P.; Akalin, G., Synthesis and antituberculosis activity of new thiazolylhydrazone derivatives. Eur J Med Chem 2008, 43, 981-985.
  45. http://dx.doi.org/10.1016/j.ejmech.2007.07.001 DOI: https://doi.org/10.1016/j.ejmech.2007.07.001
  46. Turan-Zitouni, G.; Kaplanc?kl?, Z. A.; zdemir, A., Synthesis and antituberculosis activity of some N-pyridyl- N?-thiazolylhydrazine derivatives. Eur J Med Chem 2010, 45, 2085-2088.
  47. http://dx.doi.org/10.1016/j.ejmech.2010.01.017 DOI: https://doi.org/10.1016/j.ejmech.2010.01.017
  48. Sankar, C.; Pandiarajan, K., Synthesis and anti-tubercular and antimicrobial activities of some 2r, 4 c-diaryl-3-azabicyclo [3.3. 1] nonan-9-one N-isonicotinoylhydrazone derivatives. Eur J Med Chem 2010, 45, 5480-5485.
  49. http://dx.doi.org/10.1016/j.ejmech.2010.08.024 DOI: https://doi.org/10.1016/j.ejmech.2010.08.024
  50. Bairwa, R.; Kakwani, M.; Tawari, N. R.; Lalchandani, J.; Ray, M. K.; Rajan, M. G. R.; Degani, M. S., Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents. Bioorg Med Chem Lett 2010, 20, 1623-1625.
  51. http://dx.doi.org/10.1016/j.bmcl.2010.01.031 DOI: https://doi.org/10.1016/j.bmcl.2010.01.031
  52. Correia, C.; Carvalho, M. A.; Proena, M. F., Synthesis and in vitro activity of 6-amino-2, 9-diarylpurines for Mycobacterium tuberculosis. Tetrahedron 2009, 65, 6903-6911.
  53. http://dx.doi.org/10.1016/j.tet.2009.06.065 DOI: https://doi.org/10.1016/j.tet.2009.06.065
  54. Khoje, A. D.; Kulendrn, A.; Charnock, C.; Wan, B.; Franzblau, S.; Gundersen, L.-L., Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring. Bioorg Med Chem 2010, 18, 7274-7282.
  55. http://dx.doi.org/10.1016/j.bmc.2010.08.016 DOI: https://doi.org/10.1016/j.bmc.2010.08.016
  56. Singh, K.; Singh, K.; Wan, B.; Franzblau, S.; Chibale, K.; Balzarini, J., Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity. Eur J Med Chem 2011, 46, 2290-2294.
  57. http://dx.doi.org/10.1016/j.ejmech.2011.03.010 DOI: https://doi.org/10.1016/j.ejmech.2011.03.010
  58. Gasse, C.; Douguet, D.; Huteau, V.; Marchal, G.; Munier-Lehmann, H.; Pochet, S., Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: Synthesis and in vitro anti-mycobacterial activity. Bioorg Med Chem 2008, 16, 6075-6085.
  59. http://dx.doi.org/10.1016/j.bmc.2008.04.045 DOI: https://doi.org/10.1016/j.bmc.2008.04.045
  60. Odell, L. R.; Nilsson, M. T.; Gising, J.; Lagerlund, O.; Muthas, D.; Nordqvist, A.; Karln, A.; Larhed, M., Functionalized 3-amino-imidazo [1, 2-a] pyridines: A novel class of drug-like Mycobacterium tuberculosis glutamine synthetase inhibitors. Bioorg Med Chem Lett 2009, 19, 4790-4793.
  61. http://dx.doi.org/10.1016/j.bmcl.2009.06.045 DOI: https://doi.org/10.1016/j.bmcl.2009.06.045
  62. Fassihi, A.; Azadpour, Z.; Delbari, N.; Saghaie, L.; Memarian, H. R.; Sabet, R.; Alborzi, A.; Miri, R.; Pourabbas, B.; Mardaneh, J.; Mousavi, P.; Moeinifard, B.; Sadeghi-aliabadi, H., Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides. Eur J Med Chem 2009, 44, 3253-3258.
  63. http://dx.doi.org/10.1016/j.ejmech.2009.03.027 DOI: https://doi.org/10.1016/j.ejmech.2009.03.027
  64. Mantu, D.; C?t?lina Luca, M.; Moldoveanu, C.; Zbancioc, G.; Mangalagiu, I. I., Synthesis and antituberculosis activity of some new pyridazine derivatives. Part II. Eur J Med Chem 2010, 45, 5164-5168.
  65. http://dx.doi.org/10.1016/j.ejmech.2010.08.029 DOI: https://doi.org/10.1016/j.ejmech.2010.08.029
  66. Gzel, .; Karal?, N.; Salman, A., Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg Med Chem 2008, 16, 8976-8987.
  67. http://dx.doi.org/10.1016/j.bmc.2008.08.050 DOI: https://doi.org/10.1016/j.bmc.2008.08.050
  68. Karal?, N.; Grsoy, A.; Kandemirli, F.; Shvets, N.; Kaynak, F. B.; zbey, S.; Kovalishyn, V.; Dimoglo, A., Synthesis and structureantituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem 2007, 15, 5888-5904.
  69. http://dx.doi.org/10.1016/j.bmc.2007.05.063 DOI: https://doi.org/10.1016/j.bmc.2007.05.063
  70. Kamal, A.; Shetti, R. V. C. R. N. C.; Azeeza, S.; Ahmed, S. K.; Swapna, P.; Reddy, A. M.; Khan, I. A.; Sharma, S.; Abdullah, S. T., Anti-tubercular agents. Part 5: Synthesis and biological evaluation of benzothiadiazine 1,1-dioxide based congeners. Eur J Med Chem 2010, 45, 4545-4553.
  71. http://dx.doi.org/10.1016/j.ejmech.2010.07.015 DOI: https://doi.org/10.1016/j.ejmech.2010.07.015
  72. Termentzi, A.; Khouri, I.; Gaslonde, T.; Prado, S.; Saint-Joanis, B.; Bardou, F.; Amanatiadou, E. P.; Vizirianakis, I. S.; Kordulakova, J.; Jackson, M.; Brosch, R.; Janin, Y. L.; Daff, M.; Tillequin, F.; Michel, S., Synthesis, biological activity, and evaluation of the mode of action of novel antitubercular benzofurobenzopyrans substituted on A ring. Eur J Med Chem 2010, 45, 5833-5847.
  73. http://dx.doi.org/10.1016/j.ejmech.2010.09.048 DOI: https://doi.org/10.1016/j.ejmech.2010.09.048
  74. Santos, J. L.; Yamasaki, P. R.; Chin, C. M.; Takashi, C. H.; Pavan, F. R.; Leite, C. Q. F., Synthesis and in vitro anti Mycobacterium tuberculosis activity of a series of phthalimide derivatives. Bioorg Med Chem 2009, 17, 3795-3799.
  75. http://dx.doi.org/10.1016/j.bmc.2009.04.042 DOI: https://doi.org/10.1016/j.bmc.2009.04.042
  76. Yoya, G. K.; Bedos-Belval, F.; Constant, P.; Duran, H.; Daff, M.; Baltas, M., Synthesis and evaluation of a novel series of pseudo-cinnamic derivatives as antituberculosis agents. Bioorg Med Chem Lett 2009, 19, 341-343.
  77. http://dx.doi.org/10.1016/j.bmcl.2008.11.082 DOI: https://doi.org/10.1016/j.bmcl.2008.11.082
  78. D'Oca, C. D. R. M.; Coelho, T.; Marinho, T. G.; Hack, C. R. L.; da Costa Duarte, R.; da Silva, P. A.; D'Oca, M. G. M., Synthesis and antituberculosis activity of new fatty acid amides. Bioorg Med Chem Lett 2010, 20, 5255-5257.
  79. http://dx.doi.org/10.1016/j.bmcl.2010.06.149 DOI: https://doi.org/10.1016/j.bmcl.2010.06.149
  80. Palomino, J. C.; Ramos, D. F.; da Silva, P. A., New anti-tuberculosis drugs: strategies, sources and new molecules. Curr Med Chem 2009, 16, 1898-1904.
  81. http://dx.doi.org/10.2174/092986709788186066 DOI: https://doi.org/10.2174/092986709788186066
  82. Rivers, E. C.; Mancera, R. L., New anti-tuberculosis drugs in clinical trials with novel mechanisms of action. Drug Discov Today 2008, 13, 1090-1098.
  83. http://dx.doi.org/10.1016/j.drudis.2008.09.004 DOI: https://doi.org/10.1016/j.drudis.2008.09.004
  84. Shi, R.; Sugawara, I., Development of new anti-tuberculosis drug candidates. Tohoku J Exp Med 2010, 221, 97-106.
  85. http://dx.doi.org/10.1620/tjem.221.97 DOI: https://doi.org/10.1620/tjem.221.97
  86. Asif, M., A review of antimycobacterial drugs in development. Mini Rev Med Chem 2012, 12, 1404-1418.
  87. http://dx.doi.org/10.2174/13895575112091404 DOI: https://doi.org/10.2174/13895575112091404
  88. http://dx.doi.org/10.2174/138955712804586657 DOI: https://doi.org/10.2174/138955712804586657
  89. Janin, Y. L., Antituberculosis drugs: ten years of research. Bioorg Med Chem 2007, 15, 2479-2513.
  90. http://dx.doi.org/10.1016/j.bmc.2007.01.030 DOI: https://doi.org/10.1016/j.bmc.2007.01.030

Author information

Rights and permissions

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

About this article

Cite this article

(1)
Asif, M. Antitubercular Drugs: Advances in Nitrogen Containing Heterocyclic Compounds and Some Other Derivatives. J Pharm Chem 2014, 1 (2), 37-43. https://doi.org/10.14805/jphchem.2014.art15.
Received
April 15, 2014
Published
July 28, 2014
Section
Research Reviews
Pages
37-43

Keywords