Synthesis of novel 1,2,3-triazole derivatives of isoniazid and their in vitro and in vivo antimycobacterial activity evaluation

European Journal of Medicinal Chemistry

Volumn 81, Issue , 2014, Pages 301-313

  Kumar, Deepak ^a   Beena, ^a   Khare, Garima ^a   Kidwai, Saqib ^b   Tyagi, Anil K ^a   Singh, Ramandeep ^b   Rawat, Diwan S ^a  

^a UNIVERSITY OF DELHI   (India)

^b Vaccine and Infectious Disease Research Centre   (India)

Author keywords

Antimycobacterial; In vivo; Isoniazid; LL 3858; MDR TB; TDR TB

Indexed keywords

1 AZIDOPROPANE; 1,2,3 TRIAZOLE DERIVATIVE; 4 (2 AZIDOETHOXY) BENZALDEHYDE; 4 (2 BROMOETHOXY) BENZALDEHYDE; 4 (PROP 2 YNYLOXY)BENZALDEHYDE; 4 [(1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]BENZALDEHYDE; 4 [(1 BUTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]BENZALDEHYDE; 4 [(1 ISOPROPYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]; 4 [(1 PENTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]BENZALDEHYDE; 4 [(1 PROPYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]BENZALDEHYDE; 4 [2 (4 BUTYL 1H 1,2,3 TRIAZOL 1 YL)ETHOXY] BENZALDEHYDE; 4 [2 [4 (1 HYDROXYCYCLOHEXYL) 1H 1,2,3 TRIAZOL 1 YL]ETHOXY] BENZALDEHYDE; 4 [2 [4 (4 TOLYLOXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]ETHOXY] BENZALDEHYDE; 4 [2 [4 (HYDROXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]ETHOXY] BENZALDEHYDE; 4 [2 [4 (PHENOXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]ETHOXY] BENZALDEHYDE; 4 [2 [4 (PYRIDIN 2 YL) 1H 1,2,3 TRIAZOL 1 YL]ETHOXY] BENZALDEHYDE; 4 [2 [4 [(4 CHLOROPHENOXY)METHYL] 1H 1,2,3 TRIAZOL 1 YL] ETHOXY]BENZALDEHYDE; 4 [3 (4 BUTYL 1H 1,2,3 TRIAZOL 1 YL)PROPOXY]BENZALDEHYDE; 4 [3 (4 PROPYL 1H 1,2,3 TRIAZOL 1 YL)PROPOXY]BENZALDEHYDE; 4 [3 [4 (1 HYDROXYCYCLOHEXYL) 1H 1,2,3 TRIAZOL 1 YL] PROPOXY]BENZALDEHYDE; 4 [3 [4 (4 TOLYLOXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]PROPOXY] BENZALDEHYDE; 4 [3 [4 (HYDROXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]PROPOXY] BENZALDEHYDE; 4 [3 [4 (PHENOXYMETHYL) 1H 1,2,3 TRIAZOL 1 YL]PROPOXY] BENZALDEHYDE; 4 [3 [4 [(4 CHLOROPHENOXY)METHYL] 1H 1,2,3 TRIAZOL 1 YL] PROPOXY]BENZALDEHYDE; ISONIAZID; N' [4 [2 [4 [(4 CHLOROPHENOXY)METHYL]1H 1,2,3 TRIAZOL 1 YL]ETHOXY]BENZYLIDENE] ISONICOTINOHYDRAZIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1 [2 (4 FORMYLPHENOXY)ETHYL] 1H 1,2,3 TRIAZOL 4 YL]METHYL PROPIONATE; [1 [3 (4 FORMYLPHENOXY)PROPYL] 1H 1,2,3 TRIAZOL 4 YL] METHYL PROPIONATE; TRIAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMYCOBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DOSE INCREASE; DRUG MEGADOSE; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; LUNG; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; SPLEEN; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUBERCULOSIS, PULMONARY;

ANIMALS; ANTITUBERCULAR AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ISONIAZID; MICE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; TUBERCULOSIS, PULMONARY;

EID: 84901369757     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.005     Document Type: Article

References (71)

1. Beena, and D.S. Rawat Med. Res. Rev. 33 2013 693 764
2. http://whqlibdoc.who.int/publications/2011/9789241564380-eng.pdf.
3. http://whoindia.org/en/Section3/Section123.htm.
4. R.A.M. Breen, L. Swaden, J. Ballinger, and M.C.I. Lipman Drugs 66 2006 2299 2308
5. S. Swaminathan, C. Padmapriyadarsini, and G. Narendran Clin. Infect. Dis. 50 2010 1377 1386
6. M.R. Masjedi, P. Farnia, S. Sorooch, M.V. Pooramiri, S.D. Mansoori, A.Z. Zarifi, V.A. Akbar, and S. Hoffner Clin. Infect. Dis. 43 2006 841 847
7. A.S. Albanna, and D. Menzies Drugs 71 2011 815 825
8. G.B. Migliori, G. De Iaco, G. Besozzi, R. Centis, and D.M. Cirillo Euro Surveill. 12 2007 E070517.1
9. A.A. Velayati, M.R. Masjedi, P. Farnia, P. Tabarsi, J. Ghanavi, and A.H. ZiaZarifi Chest 136 2009 420 425
10. K. Rowland Nature News 2012 http://www.nature.com/news/totally-drug- resistant-tb-emerges-in-india-1.9797
11. S. Loewenberg Lancet 379 2012 205
12. A.S. Fauci J. Infect. Dis. 197 2008 1493 1498
13. P. Ahirrao Mini-Rev. Med. Chem. 8 2008 1441 1451
14. http://www.newtbdrugs.org/pipeline.php.
15. B. Villemagne, C. Crauste, M. Flipo, A.R. Baulard, B. Deprez, and N. Willand Eur. J. Med. Chem. 51 2012 1 16
16. A.M. Ginsberg Tuberculosis 90 2010 162 167
17. S.T. Cole, and G. Riccardi Curr. Opin. Microbiol. 14 2011 570 576
18. A.H. Diacon, P.R. Donald, A. Pym, M. Grobusch, R.F. Patientia, R. Mahanyele, N. Bantubani, R. Narasimooloo, T. De Marez, R. van Heeswijk, N. Lounis, P. Meyvisch, K. Andries, and D.F. McNeeley Antimicrob. Agents Chemother. 56 2012 3271 3276
19. R. Mahajan Int. J. App. Basic Med. Res. 3 2013 1 2
20. M.S. Butler, M.A. Blaskovich, and M.A. Cooper J. Antibiot. 66 2013 571 591
21. H.A. Offe, W. Siefken, and G. Domagk Naturwissenschaften 39 1952 118
22. E. Grunberg, and R.J. Schnitzer Proc. Soc. Exp. Biol. Med. 84 1953 220
23. Y. Zhang, B. Heym, B. Allen, D. Young, and S. Cole Nature 358 1992 591 593
24. X. Zhao, H. Yu, S. Yu, F. Wang, J.C. Sacchettini, and R.S. Magliozzo Biochemistry 45 2006 4131 4140
25. M. Nguyen, C. Claparols, J. Bernadou, and B. Meunier Chem. Bio. Chem. 2 2001 877 883
26. R. Maccari, R. Ottana, F. Monforte, and M.G. Vigorita Antimicrob. Agents Chemother. 46 2002 294 299
27. T.H. Manjashetty, P. Yogeeswari, and D. Sriram Bioorg. Med. Chem. Lett. 21 2011 2125 2128
28. A.V. Ramani, A. Monika, V.L. Indira, G. Karyavardhi, J. Venkatesh, V.U. Jeankumar, T.H. Manjashetty, P. Yogeeswari, and D. Sriram Bioorg. Med. Chem. Lett. 22 2012 2764 2767
29. M.J. Hearn, M.H. Cynamon, M.F. Chen, R. Coppins, J. Davis, H.J. Kang, A. Noble, B.T. Sekine, M.S. Terrot, D. Trombino, M. Thai, E.R. Webster, and R. Wilson Eur. J. Med. Chem. 44 2009 4169 4178
30. E. Vavrikova, S. Polanc, M. Kocevar, K. Horvati, S. Bosze, J. Stolarikova, K. Vavrova, and J. Vinsova Eur. J. Med. Chem. 46 2011 4937 4945
31. E. Vavrikova, S. Polanc, M. Kocevar, J. Kosmrlj, K. Horvati, S. Bosze, J. Stolarikova, A. Imramovsky, and J. Vinsova Eur. J. Med. Chem. 46 2011 5902 5909
32. N. Boechat, V.F. Ferreira, S.B. Ferreira, M.L.G. Ferreira, F.C. Silva, M.M. Bastos, M.S. Costa, M.C.S. Lourenco, A.C. Pinto, A.U. Krettli, A.C. Aguiar, B.M. Teixeira, N.V. Silva, P.R.C. Martins, F.A.F.M. Bezerra, A.L.S. Camilo, G.P. Silva, and C.C.P. Costa J. Med. Chem. 54 2011 5988 5999
33. P. De, G.K. Yoya, P. Constant, F.B. Belval, H. Duran, N. Saffon, M. Daffe, and M. Baltas J. Med. Chem. 54 2011 1449 1461
34. S.K. Arora, N. Sinha, S. Jain, R.S. Upadhayaya, G. Jain, S. Ajay, R.K. Sinha, International Patent 2004 WO/2004/026828.
35. http://www.ctri.nic.in/Clinicaltrials/pmaindet2.php?trialid=922.
36. http://www.newtbdrugs.org/project.php?id=155.
37. G. Biagi, G. Dell'Omodarme, M. Ferretti, I. Giorgi, O. Livi, and V. Scartoni Farmaco 45 1990 1181 1192
38. K. Dabak, O. Sezer, A. Akar, and O. Anac Eur. J. Med. Chem. 38 2003 215 218
39. E. Banfi, G. Scialino, D. Zampieri, M.G. Mamolo, L. Vio, M. Ferrone, M. Fermeglia, M.S. Paneni, and S. Pricl J. Antimicrob. Chemother. 58 2006 76 84
40. B.S. Holla, M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali, and N.S. Kumari Eur. J. Med. Chem. 40 2005 1173 1178
41. A.J. Srivastava, S. Swarup, V.K. Saxena, and B.L. Chowdhury J. Indian Chem. Soc. 68 1991 103 104
42. R.J. Singh Rasayan J. Chem. 2 2009 706 708
43. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenco, J.C. Hamel, R.D. Schaadt, D. Stapertand, and B.H. Yagi J. Med. Chem. 43 2000 953 970
44. Z.Y. Zhang, Y. Liu, and S. Yang Pharm. Sin. 26 1991 809 814
45. A.C. Cunha, J.M. Figueiredo, J.L.M. Tributino, A.L.P. Miranda, H.C. Castro, R.B. Zingali, C.A.M. Fraga, M.C.B.V. de Souza, V.F. Ferreira, and E.J. Barreiro Bioorg. Med. Chem. 11 2003 2051 2059
46. Q. Zhang, Y. Peng, X.I. Wang, S.M. Keenan, S. Arora, and W.J. Welsh J. Med. Chem. 50 2007 749 754
47. K.H. Bechet, W. Draber, and K. Regal Drugs Germ 15 1972 79 82
48. M.D. Kakwani, N.H.P. Desai, A.C. Lele, M. Ray, M.G.R. Rajan, and M.S. Degani Bioorg. Med. Chem. Lett. 21 2011 6523 6526
49. B. Meunier Acc. Chem. Res. 41 2008 69 77
50. V. Pokrovskaya, and T. Baasov Expert Opin. Drug Discov. 5 2010 883 902
51. L.F. Tietze, H.P. Bell, and S. Chandrasekhar Angew. Chem. Int. Ed. 42 2003 3996 4028
52. M.C. Joshi, G.S. Bisht, and D.S. Rawat Bioorg. Med. Chem. Lett. 17 2007 3226 3230
53. H. Atheaya, S.I. Khan, R. Mamgain, and D.S. Rawat Bioorg. Med. Chem. Lett. 18 2008 1446 1449
54. Beena, N. Kumar, R.K. Rohilla, N. Roy, D.S. Rawat, and Bioorg Med. Chem. Lett. 19 2009 1396 1398
55. N. Kumar, S.I. Khan, Beena, G. Rajalakshmi, P. Kumaradhas, and D.S. Rawat Bioorg. Med. Chem. 17 2009 5632 5638
56. S. Manohar, S.I. Khan, and D.S. Rawat Bioorg. Med. Chem. Lett. 20 2010 322 325
57. D. Kumar, S. Joshi, R.K. Rohilla, N. Roy, and D.S. Rawat Bioorg. Med. Chem. Lett. 20 2010 893 895
58. D. Kumar, R.K. Rohilla, N. Roy, and D.S. Rawat Chem. Biol. Int. 1 2011 263 278
59. N. Kumar, S.I. Khan, H. Atheaya, R. Mamgain, and D.S. Rawat Eur. J. Med. Chem. 46 2011 2816 2827
60. M. Sharma, P. Joshi, N. Kumar, S. Joshi, R.K. Rohilla, N. Roy, and D.S. Rawat Eur. J. Med. Chem. 46 2011 480 487
61. S. Manohar, U.C. Rajesh, S.I. Khan, B.L. Tekwani, and D.S. Rawat ACS Med. Chem. Lett. 3 2012 555 559
62. Beena, S. Joshi, N. Kumar, S. Kidwai, R. Singh, and D.S. Rawat Arch. Pharm. Chem. Life Sci. 345 2012 896 901
63. Beena, D. Kumar, and D.S. Rawat Bioorg. Med. Chem. Lett. 23 2013 641 645
64. D. Kumar, K.K. Raj, M. Bailey, T. Alling, T. Parish, and D.S. Rawat Bioorg. Med. Chem. Lett. 23 2013 1365 1369
65. M.J. Khoshkholgh, S. Balalaie, R. Gleiter, and F. Rominger Tetrahedron 6 2008 10924 10929
66. M.V.B. Dias, I.B. Vasconcelos, A.M.X. Prado, V. Fadel, L.A. Basso, W.F. de Azevedo, and D.S. Santos J. Struct. Biol. 159 2007 369 380
67. R.C. Hartkoorn, C. Sala, J. Neres, F. Pojer, S. Magnet, R. Mukherjee, S. Uplekar, S. Boy-Rottger, K.H. Altmann, and S.T. Cole EMBO Mol. Med. 4 2012 1032 1042
68. Maestro, version 9.6 2014 Schrödinger LLC New York
69. M. Harel, D.M. Quinn, H.K. Nair, I. Silman, and J.L. Sussman J. Am. Chem. Soc. 118 1996 2340
70. G. Kryger, I. Silman, and J.L. Sussman Structure 7 1999 297
71. F.C. Bernstein, T.F. Koetzle, G.J. Williams, E.F. Meyer Jr., M.D. Brice, J.R. Rodgers, O. Kennard, T. Shimanouchi, and M. Tasumi J. Mol. Biol. 12 1977 535