Recent advances on isoniazide derivatives

Anti-Infective Agents in Medicinal Chemistry

Volumn 7, Issue 1, 2008, Pages 12-31

  Vinsova, Jarmila ^a   Imramovsky, Ales ^a   Jampilek, Josef ^b   Monreal, Juana Ferriz ^a   Dolezal, Martin ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b Zentiva Prague   (Czech Republic)

Author keywords

Antimycobacterial activity; Isoniazide; Isoniazide derivatives; M. tuberculosis; Multidrug resistance; Structure activity relationships

Indexed keywords

5 (3 CHLOROBENZYLIDENE) 2 (ISONICOTINOYLHYDRAZINO) IMIDAZOLINE 4 ONE; ACYLTRANSFERASE; CHELATE; CIPROFLOXACIN; COBALT ISONIAZID CHELATE; COPPER ISONIAZID CHELATE; ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADPH); FATTY ACID SYNTHASE; GLUTAMATE SYNTHASE (NADH); HYDRAZIDE DERIVATIVE; HYDRAZONE DERIVATIVE; ISONIAZID; ISONIAZID DERIVATIVE; ISONIAZID NICKLE CHELATE; KATG PROTEIN; N2 CYCLOHEXYLIDENYL ISONICOTINIC ACID HYDRAZIDE; PYRAZINAMIDE; PYRIDOXAL ISONICOTINOYLHYDRAZONE; PYRIDOXINE; PYRROLE DERIVATIVE; QUINOLONE; THIAZOLIDINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

AFRICA; ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; BACTERIAL STRAIN; BACTERIAL VIRULENCE; CONFORMATIONAL TRANSITION; DRUG ANALYSIS; DRUG CONFORMATION; EASTERN EUROPE; EUROPE; HUMAN; MULTIDRUG RESISTANCE; MYCOBACTERIUM TUBERCULOSIS; QUANTITATIVE ANALYSIS; REVIEW; SOUTHEAST ASIA; STRAIN DIFFERENCE; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS; WESTERN HEMISPHERE;

EID: 41149118879     PISSN: 18715214     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152108783329780     Document Type: Review

References (85)

1. http://www.who.int/mediacentre/factsheets/fs104/en/ (15 November 2006).
2. Koch, R. Berliner Klin. Wochenschr., 1882, 19, 221.
3. Cole, S.T.; Brosch, R.; Parkhill J.; Garnier, T.; Churcher, C.; Hartus. D.; Gordon, S.V.; Eiglmeier, N.K.; Gas, C.; Barry, E.; Tekaia F.; Badcock, K.; Baham, D.; Brown D.; Chillingworth, T.; Conner, R.; Davies, R.; Delvin, K.; Feltwell, T.; Gentles, S.; Hamlin, N.; Holroyd, S.; Hornsby, T.; Jagels, K.; Krogh, A.; McLean, J.; Moule, S.; Murphy, L.; Olivek, K.; Osborne, J.; Quail, M.A.; Rajandream, M.A.; Rogers, J.; Rutter, S.; Server, K.; Skeleton, J.; Squares, R.; Squares, S.; Sulston, J.E.; Tailor, K.; Whitehead, S.; Barrell, B.G. Nature, 1998, 393, 537.
4. http://genolist.pasteur.fr/TubercuList/ (15 November 2006)
5. Hong, X.; Hopfinger, A.J. Biomacromolecules, 2004, 5, 1066.
6. Brennan, P.J. Annu. Rev. Biochem., 1995, 64, 29.
7. http://www.CHEMSOC.ORG/chembytes/ezine/1998/evans.htm (15 November 2006)
8. Baum, R.M. Chem. Eng. News, 2005, 83, 76.
9. Fox, H.H. Science, 1952, 116, 129.
10. Bernstein, J.W.; Lott, W.A.; Steinberg, B.A.;Yale, H.L. Am. Rev. Tuberc., 1952, 65, 357.
11. Whitney, J.B.; Wainberg, M.A. McGill J. Med., 2002, 6, 114.
12. Chang, G.; Spencer, R.H; Lee, A.T.; Barclay, M.T.; Rees, D.C. Science, 1998, 282, 2220.
13. Benetton, S.A.; Kedor-Hackmann, E.R.M.; Santoro, M.I.R.M.; Borges, V.M. Talanta, 1998, 47, 639.
14. Wang, J.Y.; Burger, R.M.; Drlica, K. Antimicrob. Agents Chemother., 1998, 42, 709.
15. Bardou, F.; Raynaud, C.; Ramos, C.; Laneelle; M.A.; Lancelle, G. Microbiology, 1998, 144, 2539.
16. Zabinski, R.F.; Blanchard, J.S. J. Am. Chem. Soc., 1997, 119, 2331.
17. Bodiguel, J.; Nagy, J.M.; Brown, K.A.; Jamart-Grégoire, B. J. Am. Chem. Soc., 2001, 123, 3832.
18. Mduli, K.; Sherman, D.; Hickey, M.; Kreiswirth, B.; Morris, S., Stover, C.K.; Barry, C.E. J. Infect. Dis., 1996, 174, 1085.
19. Wild, I.; van Helden, E.H.; Hon, D.; Lombard, C.; van Helden, P. Antimicrob. Agents Chemother., 1999, 43, 975.
20. Sherman, D.R, Mdiuli, K.; Hickey, M.J.; Barry, C.E.; Stover, C.K. Biofactors, 1999, 10, 211.
21. Samson, N.S.; Vrielink, A. Acc. Chem. Res., 2003, 36, 713.
22. Pope, H. Am. Rev. Antituberc., 1953, 68, 938.
23. Takayama, K.; Schnoes, H.K.; Amstrong, E.L.; Boyle, R. W. J. Lipid Res., 1975, 16, 308.
24. Banerje, A.; Dubnau, E.; Quemard, A.; Balasubramanian, V.; Um, K.S.; Wilson, T.; Collins, D.; de Lisle, G.; Jacobs, Jr. W.R. Science, 1994, 263, 227.
25. Dessen, A.; Quemard, A.; Blanchard, J.S.; Jacobs Jr, W.R.; Sacchettini, J.C. Science, 1995, 267, 1638.
26. Lee, A.S.; Lim, S.I.; Tang, L.L.; Telenti, A.; Wong, S.Y. Antimicrob. Agents Chemother., 1999, 43, 2087.
27. Mdluli K.; Sladyen, R.A.; Zhu, Y.Q.; Ramaswamy, S.; Pan, X; Mead, D.; Crane, D.D.; Musser, J.M.; Barry, C.E. Science, 1998, 280, 1607.
28. Rozwarsky, D.A.; Grant, G.A.; Barton, D.H.R.; Jacobs; W.R., Jr.; Sacchettini, J.C. Science, 1998, 279, 98.
29. Brindley, D.N.; Matsumura, S.; Bloch, K. Nature, 1999, 224, 666.
30. Vilcheze, C.; Morbidoni, H.R.; Wisbrod, T.R.; Iwamoto, H.; Kuo, M.; Sacchettini J.C.; Jacobs Jr, W.R. J. Bacteriol., 2000, 182, 4059.
31. Petrini, B.; Hoffner, S. Int. J. Antimicrob. Agents, 1999, 13, 93.
32. Telenti A., Honore N., Bernasconi C. March, J.; Ortega, A.; Heym, B.; Takiff, H.H.; Cole, S.T. J. Clin. Microbiol, 1997, 35, 719.
33. Heym, B.; Zang, Y.; Poulet, S.; Young, D.; Cole, S.T. J. Bacteriol., 1993, 175, 4255.
34. Sander, P.; Böttger, E.C. Chemotherapy, 1999, 45, 95.
35. Cohen, T.; Becerra, M.C.; Murray, M.B. Microbial Drug Resistance, 2004, 10, 280.
36. Ramaswamy, S.; Musser, J. Tubercle and Lung Disease, 1998, 79, 3.
37. Ofee, H.; Siefken, W.; Domagk, G. Z. Naturforsch. B. Chem. Sci., 1952, 7, 462.
38. Fujikawa, F., Hirai, K.; Hirayama, T.; Kumoto, K.; Matsuoka, M.; Toyoda, G.; Yasuda, S.; Osaki, M.; Naito, M.; Tsukuma, S.; Mabuchi, H. Yakugaku Zasshi, 1970, 90, 78.
39. Klopman, G; Fercu, D.; Jacob, J. Chem Phys., 1996, 204, 181.
40. Pasqualoto, K.F.M.; Ferreira, E.I.; Santos, O.A.; Hopfinger, A.J. J. Med. Chem., 2004, 47, 3755.
41. Seydel, J.K.; Schaper, K.J.; Wempe, E.; Cordes, H.P. J. Med. Chem., 1976, 19, 483.
42. Maccari, R.; Ottana, R.; Bottari, B.; Rotondo, E.; Vigorita, M. G. Bioorg. Med. Chem. Lett., 2004, 14, 5731.
43. Kakimoto, S.; Tone, I. J. Med. Chem., 1965, 8, 868.
44. Osman, S.A.A.; Abdalla, A.A.; Alaib, M.O. J. Pharm. Sci., 1983, 72, 68.
45. Kakimoto, S.; Tone, J. Med. Chem., 1965, 8, 878.
46. Suriyati, M.; Pazilah, I.; Amirin, S. Tuberculosis, 2004, 8, 56.
47. Desai, P.B. Orient. J. Chem., 1999, 15, 301.
48. Szymanska, E.; Kiec-Kononowicz, K. Farmaco, 2002, 57, 355.
49. Arora, S.K.; Sinha, N.; Jain, S.; Upadhayaya, R.S.; Jana, G.; Ajay, S.; Sinha, R.K. (Patent To Lupin Limited, India), Patent: WO, 2004, 26828; Chem Abstr. 140, 287261.
50. Vigorita, M.G.; Basile, M.; Zappala, C.; Gabbrielli, G.; Pizzimenti, F.C. Farmaco, 1992, 47, 893.
51. Mamolo, M.G.; Zampieri, D.; Vio, L.; Fermeglia, M.; Ferrone, M.; Pricl, S.; Scialino, G.; Banfi, E. Bioorg. Med. Chem., 2005, 13, 3797.
52. Bottari, B.; Maccari, R.; Monforte, F.; Ottana, R.; Rotondo, E.; Vigorita, M.G. Bioorg. Med. Chem. Lett., 2000, 10, 657.
53. Maccasi, R.; Ottana, R.; Monforte, F.; Vigorita, M.G. Antimicrob. Agents Chemother., 2002, 46, 294.
54. Georgieva, N.; Gadjeva, V. Biochemistry (Moscow), 2002, 67, 588.
55. Garcia-Garcia, A.; Galvez, J.; De, J.O. J.; Garcia-Domenech, R.; Munoz, C.; Guna, R.; Borras, R. J. Antimicrob. Chemother., 2003, 53, 65.
56. El-Shaaer, H.M.; Foltinova, P.; Lacova, M.; Chovancov A, J.; Stankovicova, H. Farmaco, 1998, 53, 224.
57. Buss, J.L.; Ponka, P. Biochim. Biophys. Acta, 2003, 1619, 177.
58. Hearn, M.J.; Cynamon, M.H. J. Antimicrob. Chemother., 2004, 53, 185.
59. Alagarsamy, V.; Venkateshperumal, R.; Sathyabhama, S.; Vaishnavapriya, S.; Sakkarapandi, S.; Revathi, S.; Kalaiselvi, R.; Balamurugan, J.; Sevukarajan, M. Indian J. Heterocycl. Chem., 2002, 11, 327.
60. Vigorita, M.G.; Ottana, R.; Zappala, C.; Maccari, R.; Pizzimenti, F.C.; Gabbrielli, G. Farmaco, 1994, 49, 775.
61. Sriram, D.; Yogeeswari, P.; Madhu, K. Bioorg. Med. Chem. Lett., 2005, 15, 4502.
62. Sriram, D.; Yogeeswari, P.; Madhu, K. Bioorg. Med. Chem. Lett., 2006, 16, 876.
63. Bottari, B; Maccari, R; Monforte, F; Ottana, R; Vigorita, M.G.; Bruno, G; Nicolo, F; Rotondo, A.; Rotondo, E. Bioorg. Med. Chem., 2001, 9 2203.
64. Abou-Fadl, T.; Mohammed, F.A.H.; Hassan, E.A.S. Arch. Pharm. Res., 2003, 26, 778.
65. Sriram, D,; Aubry, A.; Yogeeswari, P.; Fisher, L.M. Bioorg. Med. Chem. Lett., 2006, 16, 2982.
66. Mamoto, G.M.; Vio, L.; Banfi, E. Farmaco, 1996, 51, 65.
67. Cocco, M.T.; Congiu, C.; Onnis, V.; Pusceddu, M.C.; Schivo, M.L.; De Logu, A. Eur. J. Med Chem., 1999, 34, 1071.
68. De Logu, A.; Onnis, V.; Saddi, B.; Congiu, C.; Schivo, M.L.; Cocco, M.T. J. Antimicrob. Chemother., 2002, 49, 275.
69. Glushkov, R.G.; Modnikova, G.A.; Lvov, A.I.; Krylova, L.Yu.; Pushkina, T.V.; Guskova, T.A.; Soloveva, N.P. Pharm. Chem. J., 2004, 38, 420.
70. Sinha, N.; Jain, S.; Tilekar, A.; Upadhayaya, R.S.; Kishore, N.; Jana, G.H.; Arora, S.K. Bioorg. Med. Chem. Lett., 2005, 15, 1573.
71. Shaharyar, M.; Siddiqui, A.A.; Ali, M.A.; Sriram, D.; Yogeeswari, P. Bioorg. Med. Chem. Lett., 2006, 16, 3947.
72. Bottari, B.; Maccari, R.; Monforte, F.; Ottana, R.; Rotondo, E.; Vigorita, M.G. Bioorg. Med. Chem. Lett., 2000, 10, 657.
73. Bottari, B.; Maccari, R.; Monforte, F.; Ottana, R.; Rotondo, E.; Vigorita, M.G. Bioorg. Med. Chem. Lett., 2001, 11, 301.
74. Maccari, R.; Ottana, R.; Bottari, B.; Rotondo, E.; Vigorita, M.G. Bioorg. Med. Chem. Lett., 2004, 14, 5731.
75. Maccari, R.; Ottana, R.; Monforte, F.; Vigorita, M.G. Antimicrob. Agents Chemother., 2002, 46, 294.
76. Maccari, R.; Ottana, R.; Vigorita, M.G. Bioorg. Med. Chem. Lett., 2005, 15, 2509.
77. Jampilek, J.; Dolezal, M.; Kunes, J.; Satinsky, D.; Raich, I. Curr. Org. Chem., 2005, 9, 49.
78. Dolezal, M.; Palek, L; Vinsova, J.; Buchta, V.; Jampilek, J.; Kralova, K. Molecules, 2006, 11, 242, http://www.mdpi.org/ molecules/papers/11040242.pdf.
79. Imramovsky, A.; Polanc, S. Chem. Listy, 2005, 99, 363.
80. Imramovsky, A.; Vinsova, J.; Polanc, S.; Jampilek, J. Chem. Listy, 2005, 99, 845.
81. Imramovsky, A.; Vinsova, J.; Monreal-Ferriz, J.; Dolezal, M.; Jampilek, J. Drugs Fut., 2006, 31 (Suppl. A), 60.
82. Imramovsky, A.; Polanc, S.; Vinsova, J.; Kocevar, M.; Jampilek, J.; Reckova, Z.; Kaustova, J. Bioorg. Med. Chem., 2007, 15, 2551.
83. Imramovsky, A.; Vinsova, J.; Jampilek, J. Chem. Listy, 2006, 100, 659.
84. Jampilek, J.; Imramovsky, A.; Vinsova, J.; Dohnal, J. Chem. Listy, 2006, 100, 660.
85. Jampilek, J.; Imramovsky, A.; Vinsova, J.; Dolezal, M.; In Book of Abstracts Drug Analysis 2006, May 16-19, 2006, Namur, Belgium, PE-09.