Design, synthesis and biological evaluation of novel isoniazid derivatives with potent antitubercular activity

European Journal of Medicinal Chemistry

Volumn 81, Issue , 2014, Pages 119-138

  Martins, Filomena ^a   Santos, Susana ^a   Ventura, Cristina ^a,b   Elvas Leitão, Ruben ^a,c   Santos, Lídia ^a,f   Vitorino, Susana ^a,g   Reis, Marina ^a,b   Miranda, Vanessa ^a,h   Correia, Henrique F ^a   Aires De Sousa, João ^d   Kovalishyn, Vasyl ^d,i   Latino, Diogo A R S ^a,d   Ramos, Jorge ^e   Viveiros, Miguel ^e  

^a UNIVERSITY OF LISBON   (Portugal)

^b Instituto Superior de Educação e Ciências ISEC   (Portugal)

^c INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

^d DEPARTAMENTO DE QUÍMICA   (Portugal)

^e UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^f DEPARTAMENTO DE CIÊNCIA DOS MATERIAIS   (Portugal)

^g IMPERIAL COLLEGE LONDON   (United Kingdom)

^h INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

ⁱ INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

Antitubercular activity; Isoniazid derivatives; Mycobacterium tuberculosis; QSARs; Resistance; Synthesis

Indexed keywords

2 HYDRAZINOISONICOTINOHYDRAZIDE; HYDRAZIDE; ISONIAZID; ISONIAZID DERIVATIVE; METHYL 4 [(ISONICOTINOYLHYDRAZONE)METHYL]BENZOATE; N' (4 PHENOXYBENZYLIDENE)ISONICOTINOHYDRAZIDE; N' (4 PHENYLCYCLOHEXYL)ISONICOTINOHYDRAZIDE; N' (4 PHENYLCYCLOHEXYLIDENE)ISONICOTINOHYDRAZIDE; N' CYCLOPENTYLIDENEISONICOTINOHYDRAZIDE; N' DECANOYLISONICOTINOHYDRAZIDE; NITROGEN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; CYTOTOXICITY ASSAY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; IN VITRO STUDY; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RANDOM FOREST; VERO CELL LINE; ANALOGS AND DERIVATIVES; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CHLOROCEBUS AETHIOPS; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTITUBERCULAR AGENTS; CERCOPITHECUS AETHIOPS; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ISONIAZID; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 84900555653     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.04.077     Document Type: Article

References (117)

1. World Health Organization Global Tuberculosis Report 2013 2013 World Health Organization Geneva, Switzerland http://www.who.int/tb/publications/ global-report/en/index.html (last accessed 06.02.14.)
2. http://www.who.int/tb/publications/factsheets/en/ (last accessed 06.02.14.).
3. G.B. Migliori, G. De Iaco, G. Besozzi, R. Centis, and D.M. Cirillo First tuberculosis cases in Italy resistant to all tested drugs Eurosurveillance 12 2007
4. A.A. Velayati, M.R. Masjedi, P. Farnia, P. Tabarsi, J. Ghanavi, A.H. ZiaZarifi, and S.E. Hoffner Emergence of new forms of totally drug-resistant tuberculosis bacilli super extensively drug-resistant tuberculosis or totally drug-resistant strains in Iran Chest 136 2009 420 425
5. Z.F. Udwadia, R.A. Amale, K.K. Ajbani, and C. Rodrigues Totally drug-resistant tuberculosis in India Clinical Infectious Diseases 54 2012 579-U156
6. WHO The Stop TB Strategy, 2010. http://www.who.int/tb/strategy/stop-tb- str ategy/en/index.html (last accessed 11.04.13.).
7. Global Plan to Stop TB 2011-2015 Stop TB Partnership and World Health Organization 2010 World Health Organization Geneva (last accessed 11.04.13.) http://www.stoptb.org/global/plan/
8. A. Koul, E. Arnoult, N. Lounis, J. Guillemont, and K. Andries The challenge of new drug discovery for tuberculosis Nature 469 2011 483 490
9. S. Munack, V. Leroux, K. Roderer, M. Ökvist, A. van Eerde, L.L. Gundersen, U. Krengel, and P. Kast When inhibitors do not inhibit: critical evaluation of rational drug design targeting chorismate mutase from Mycobacterium tuberculosis Chemistry & Biodiversity 9 2012 2507 2527
10. C. Lienhardt, M. Raviglione, M. Spigelman, R. Hafner, E. Jaramillo, M. Hoelscher, A. Zumla, and J. Gheuens New drugs for the treatment of tuberculosis: needs, challenges, promise, and prospects for the future The Journal of Infectious Diseases 205 2012 S241 S249
11. H. Tomioka, Y. Tatano, K. Yasumoto, and T. Shimizu Recent advances in antituberculous drug. Development and novel drug target Expert Review of Respiratory Medicine 2 2008 455 471
12. B. Villemagne, C. Crauste, M. Flipo, A.R. Baulard, B. Déprez, and N. Willand Tuberculosis: the drug development pipeline at a glance European Journal of Medicinal Chemistry 51 2012 1 16
13. A. Zumla, P. Nahid, and S.T. Cole Advances in the development of new tuberculosis drugs and treatment regimens Nature Reviews. Drug Discovery 12 2013 388 404
14. FDA, U.S. Foods and Drugs Administration, Press Release of Dec. 31, 2012.
15. HIV-HCV-TB Pipeline Report, Drugs, Diagnostics, Vaccines & Preventive Technologies, Update February 2013. http://www.pipelinereport.org/browse/tb- treatments/bedaquiline-tmc207 (last accessed 13.02.13.).
16. Briefing document Anti-Infective Drugs Advisory Committee Meeting November 2013 Jansson Pharmaceutical Company of Johnson & Johnson http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/ Drugs/Anti-InfectiveDrugsAdvisoryCommittee/UCM329260.pdf (last accessed 11.04.13.)
17. J. Bernstein, W.A. Lott, B.A. Steinberg, and H.L. Yale Chemotherapy of experimental tuberculosis.5. Isonicotinic acid hydrazide (Nydrazid) and related compounds American Review of Tuberculosis 65 1952 357 364
18. C. Vilchèze, and W.R. Jacobs Jr. The mechanism of isoniazid killing: clarity through the scope of genetics Annual Review of Microbiology 61 2007 35 50 (Pubitemid 350058198)
19. F. Bardou, C. Raynaud, C. Ramos, M.A. Lanéelle, and G. Lanéelle Mechanism of isoniazid uptake in Mycobacterium tuberculosis Microbiology (Reading, U.K.) 144 1998 2539 2544 (Pubitemid 28457163)
20. D.A. Mitchison, and J.B. Selkon The bactericidal activities of antituberculous drugs American Review of Tuberculosis 74 1956 109 116
21. F.G. Winder, and P.B. Collins Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis Journal of General Microbiology 63 1970 41 48
22. K. Johnsson, and P.G. Schultz Mechanistic studies of the oxidation of isoniazid by the catalase peroxidase from Mycobacterium tuberculosis Journal of the American Chemical Society 116 1994 7425 7426 (Pubitemid 24274243)
23. B.F. Lei, C.J. Wei, and S.C. Tu Action mechanism of antitubercular isoniazid - activation Mycobacterium tuberculosis KatG, isolation, and characterization of InhA inhibitor The Journal of Biological Chemistry 275 2000 2520 2526
24. R. Rawat, A. Whitty, and P.J. Tonge The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: adduct affinity and drug resistance Proceedings of the National Academy of Sciences of the United States of America 100 2003 13881 13886 (Pubitemid 37499160)
25. Y. Zhang, B. Heym, B. Allen, D. Young, and S. Cole The catalase peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis Nature 358 1992 591 593
26. D. Machado, J. Perdigão, J. Ramos, I. Couto, I. Portugal, C. Ritter, E.C. Boettger, and M. Viveiros High level resistance to isoniazid and ethionamide in multidrug resistant Mycobacterium tuberculosis of the Lisboa family is associated with InhA double mutations Journal of Antimicrobial Chemotherapy 68 2013 1728 1732
27. M. Viveiros, M. Martins, L. Rodrigues, D. Machado, I. Couto, J. Ainsa, and L. Amaral Inhibitors of mycobacterial efflux pumps as potential boosters for anti-tubercular drugs Expert Review of Anti-infective Therapy 10 2012 983 998
28. D. Machado, I. Couto, J. Perdigão, L. Rodrigues, I. Portugal, P. Baptista, B. Veigas, L. Amaral, and M. Viveiros Contribution of efflux to the emergence of isoniazid and multidrug resistance in Mycobacterium tuberculosis Plos One 7 2012 e34538
29. R.Z. Pellicani, A. Stefanachi, M. Niso, A. Carotti, F. Leonetti, O. Nicolotti, R. Perrone, F. Berardi, S. Cellamare, and N.A. Colabufo Potent galloyl-based selective modulators targeting multidrug resistance associated protein 1 and P-glycoprotein Journal of Medicinal Chemistry 55 2012 424 436
30. M.H. Hazbón, M. Brimacombe, M.B. del Valle, M. Cavatore, M.I. Guerrero, M. Varma-Basil, H. Billman-Jacobe, C. Lavender, J. Fyfe, L. García-García, C.I. León, M. Bose, F. Chaves, M. Murray, K.D. Eisenach, J. Sifuentes-Osornio, M.D. Cave, A.P. de León, and D. Alland Population genetics study of isoniazid resistance mutations and evolution of multidrug-resistant Mycobactetium tuberculosis Antimicrobial Agents and Chemotherapy 50 2006 2640 2649 (Pubitemid 44198682)
31. H. van de Waterbeemd, and E. Gifford ADMET in silico modelling: towards prediction paradise? Nature Reviews. Drug Discovery 2 2003 192 204 (Pubitemid 37361664)
32. L.C. Yee, and Y.C. Wei Current modeling methods used in QSAR/QSPR M. Dehmer, K. Varmuza, D. Bonchev, Statistical Modeling of Molecular Descriptors in QSAR/QSPR 2012 Wiley-VCH Verlag GmbH & Co. KGaA Weinhein
33. R.V.C. Guido, G. Oliva, and A.D. Andricopulo Virtual screening and its integration with modern drug design technologies Current Medicinal Chemistry 15 2008 37 46 (Pubitemid 351234626)
34. K.K. Chohan, S.W. Paine, and N.J. Waters Advancements in predictive in silico models for ADME Current Chemical Biology 2 2008 215 228
35. C. Ventura, and F. Martins Application of quantitative structure-activity relationships to the modeling of antitubercular compounds. 1. The hydrazide family Journal of Medicinal Chemistry 51 2008 612 624 (Pubitemid 351252289)
36. V. Kovalishyn, J. Aires-de-Sousa, C. Ventura, R.E. Leitão, and F. Martins QSAR modeling of antitubercular activity of diverse organic compounds Chemometrics and Intelligent Laboratory Systems 107 2011 69 74
37. C. Ventura, D. Latino, F. Martins, Comparison of multiple linear regressions and neural networks based QSAR models for the design of new antitubercular compounds, European Journal of Medicinal Chemistry 70 (2013) 831-845.
38. P. Gramatica, P. Pilutti, and E. Papa Validated QSAR prediction of OH tropospheric degradation of VOCs: splitting into training-test sets and consensus modeling Journal of Chemical Information and Computer Science 44 2004 1794 1802
39. G. Klopman, D. Fercu, and J. Jacob Computer-aided study of the relationship between structure and antituberculosis activity of a series of isoniazid derivatives Chemical Physics 204 1996 181 193 (Pubitemid 126317426)
40. J.K. Seydel, K.J. Schaper, E. Wempe, and H.P. Cordes Mode of action and quantitative structure-activity correlations of tuberculostatic drugs of isonicotinic-acid hydrazide type Journal of Medicinal Chemistry 19 1976 483 492
41. S. Mohamad, P. Ibrahim, and A. Sadikun Susceptibility of Mycobacterium tuberculosis to isoniazid and its derivative, 1-isonicotinyl-2-nonanoyl hydrazine: investigation at cellular level Tuberculosis 84 2004 56 62 (Pubitemid 38082933)
42. A. De Logu, V. Onnis, B. Saddi, C. Congiu, M.L. Schivo, and M.T. Cocco Activity of a new class of isonicotinoylhydrazones used alone and in combination with isoniazid, rifampicin, ethambutol, para-aminosalicylic acid and clofazimine against Mycobacterium tuberculosis The Journal of Antimicrobial Chemotherapy 49 2002 275 282 (Pubitemid 34162617)
43. D. Sriram, P. Yogeeswari, and K. Madhu Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones Bioorganic & Medicinal Chemistry Letters 15 2005 4502 4505 (Pubitemid 41253883)
44. P. Prathipati, N.L. Ma, and T.H. Keller Global Bayesian models for the prioritization of antitubercular agents Journal of Chemical Information and Modeling 48 2008 2362 2370
45. B. Bottari, R. Maccari, F. Monforte, R. Ottana, E. Rotondo, and M.G. Vigorita Isoniazid-related copper(II) and nickel(TI) complexes with antimycobacterial in vitro activity. Part 9 Bioorganic & Medicinal Chemistry Letters 10 2000 657 660 (Pubitemid 30186672)
46. J. Bernstein, W.P. Jambor, W.A. Lott, F. Pansy, B.A. Steinberg, and H.L. Yale Chemotherapy of experimental tuberculosis.6. Derivatives of isoniazid American Review of Tuberculosis 67 1953 354 365
47. N. Georgieva, and V. Gadjeva Isonicotinoylhydrazone analogs of isoniazid: relationship between superoxide scavenging and tuberculostatic activities Biochemistry (Moscow) 67 2002 588 591 (Pubitemid 34719964)
48. M.C.D. Lourenço, M.D. Ferreira, M.V.N. de Souza, M.A. Peralta, T.R.A. Vasconcelos, and M.D.M.O. Henriques Synthesis and anti-mycobacterial activity of (E)-N′-(monosubstituted-benzylidene)isonicotinohydrazide derivatives European Journal of Medicinal Chemistry 43 2008 1344 1347 (Pubitemid 351753033)
49. M.J. Hearn, M.H. Cynamon, M.F. Chen, R. Coppins, J. Davis, H.J.O. Kang, A. Noble, B. Tu-Sekine, M.S. Terrot, D. Trombino, M. Thai, E.R. Webster, and R. Wilson Preparation and antitubercular activities in vitro and in vivo of novel schiff bases of isoniazid European Journal of Medicinal Chemistry 44 2009 4169 4178
50. C.H. Andrade, L.D. Salum, M.S. Castilho, K.F.M. Pasqualoto, E.I. Ferreira, A.D. Andricopulo, Fragment-Based, and Classical Quantitative Structure-activity relationships for a series of hydrazides as antituberculosis agents Molecular Diversity 12 2008 47 59
51. https://www.collaborativedrug.com/pages/public-access (last accessed 13.02.13.).
52. http://www.talete.mi.it/products/dragon-description.htm (last accessed 20.05.13.).
53. http://www.molecular-networks.com/products/adrianacode (last accessed 12.04.13.).
54. J.A. Platts, D. Butina, M.H. Abraham, and A. Hersey Estimation of molecular linear free energy relation descriptors using a group contribution approach Journal of Chemical Information and Computer Science 39 1999 835 845
55. J.A. Platts, M.H. Abraham, D. Butina, and A. Hersey Estimation of molecular linear free energy relationship descriptors by a group contribution approach. 2. Prediction of partition coefficients Journal of Chemical Information and Computer Science 40 2000 71 80
56. M.H. Abraham, A. Ibrahim, A.M. Zissimos, Y.H. Zhao, J. Comer, and D.P. Reynolds Application of hydrogen bonding calculations in property based drug design Drug Discovery Today 7 2002 1056 1063
57. Molecular Modeling Pro Plus, version 6.2.5. www.chemistry-software.com.
58. ChemDraw Ultra,Version 11.0.1, © 1986-2007 CambridgeSoft
59. L. Breiman Random forests Machine Learning 45 2001 5 32 (Pubitemid 32933532)
60. R Development Core Team R: a Language and Environment for Statistical Computing 2004 R Foundation for Statistical Computing Vienna, Austria 3-900051-07-0 URL http://www.R-project.org (last accessed 20.05.13.). Fortran Original by Leo Breiman, Adele Cutler, R port by Andy Liaw and Matthew Wiener. (2004)
61. I.V. Tetko Neural network studies. 4. Introduction to associative neural networks Journal of Chemical Information and Computer Science 42 2002 717 728 (Pubitemid 35355281)
62. Organization for Economic Co-operation and Development (OECD) Environment Health and Safety Publications Series on Testing and Assessment, 69, Guidance Document on the Validation of (Quantitative) Structure-Activity Relationship [(Q)SAR] Models 2007 http://www.oecd.org/fr/env/ess/risques/ guidancedocumentsandreportsrelatedtoqsars.htm (last accessed 11.04.13.)
63. A. Tropsha, P. Gramatica, and V.K. Gombar The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models QSAR & Combinatorial Science 22 2003 69 77 (Pubitemid 36717473)
64. T.I. Netzeva, A.P. Worth, T. Aldenberg, R. Benigni, M.T.D. Cronin, P. Gramatica, J.S. Jaworska, S. Kahn, G. Klopman, C.A. Marchant, G. Myatt, N. Nikolova-Jeliazkova, G.Y. Patlewicz, R. Perkins, D.W. Roberts, T.W. Schultz, D.T. Stanton, J.J.M. van de Sandt, W.D. Tong, G. Veith, and C.H. Yang Current status of methods for defining the applicability domain of (quantitative) structure-activity relationships - the report and recommendations of ECVAM workshop 52, Atla-Altern Laboratory Animals 33 2005 155 173 (Pubitemid 40686385)
65. A. Gissi, D. Gadaleta, M. Floris, S. Olla, A. Carotti, E. Novellino, E. Benfenati, and O. Nicolotti An alternative QSAR-based approach for predicting the bioconcentration factor for regulatory purposes Altex-Alternatives to Animal Experimentation 31 2014 23 36
66. J. Jaworska, N. Nikolova-Jeliazkova, and T. Aldenberg QSAR applicability domain estimation by projection of the training set in descriptor space: a review Altex-Alternatives to Animal Experimentation 33 2005 445 459 (Pubitemid 41613738)
67. A. Tropsha Best practices for QSAR model development, validation, and exploitation Molecular Informatics 29 2010 476 488
68. P. Gramatica Principles of QSAR models validation: internal and external QSAR & Combinatorial Science 26 2007 694 701 (Pubitemid 46932857)
69. D. Livingstone A Practical Guide to Scientific Data Analysis 2009 Wiley & Sons Ltd Chichester
70. C. Kim, Y. Lee, and B.U. Park Cook's distance in local polynomial regression Statistics & Probability Letters 54 2001 33 40 (Pubitemid 33623400)
71. J.A. Díaz-García, and G. González-Farías A note on the Cook's distance Journal of Statistical Planning and Inference 120 2004 119 136 (Pubitemid 37445590)
72. A. Golbraikh, and A. Tropsha Beware of q2! Journal of Molecular Graphics and Modelling 20 2002 269 276
73. P.P. Roy, S. Paul, I. Mitra, and K. Roy On two novel parameters for validation of predictive QSAR models Molecules 14 2009 1660 1701
74. N. Chirico, and P. Gramatica Real external predictivity of QSAR models: how to evaluate it? Comparison of different validation criteria and proposal of using the concordance correlation coefficient Journal of Chemical Information and Modeling 51 2011 2320 2335
75. N. Chirico, and P. Gramatica Real external predictivity of QSAR models. Part 2. New intercomparable thresholds for different validation criteria and the need for scatter plot inspection Journal of Chemical Information and Modeling 52 2012 2044 2058
76. K. Roy, I. Mitra, S. Kar, P.K. Ojha, R.N. Das, and H. Kabir Comparative studies on some metrics for external validation of QSPR models Journal of Chemical Information and Modeling 52 2012 396 408
77. 2m metrics for validation of QSPR models Chemometrics and Intelligent Laboratory Systems 107 2011 194 205
78. I. Mitra, A. Saha, and K. Roy Exploring quantitative structure-activity relationship studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants Molecular Simulation 36 2010 1067 1079
79. L. Eriksson, J. Jaworska, A.P. Worth, M.T.D. Cronin, R.M. McDowell, and P. Gramatica Methods for reliability and uncertainty assessment and for applicability evaluation of classification- and regression-based QSARs Environmental Health Perspectives 111 2003 1361 1375 (Pubitemid 37021142)
80. N. Minovski, S. Zuperl, V. Drgan, and M. Novic Assessment of applicability domain for multivariate counter-propagation artificial neural network predictive models by minimum Euclidean distance space analysis: a case study Analytica Chimica Acta 759 2013 28 42
81. G. Palla, G. Predieri, P. Domiano, C. Vignali, and W. Turner Conformational behavior and E/Z isomerization of N-acyl and N-aroylhydrazones Tetrahedron 42 1986 3649 3654
82. E. Wyrzykiewicz, and D. Prukala Isomeric N-substituted hydrazones of 2-, 3- and 4-pyridinecarboxaldehydes Journal of Heterocyclic Chemistry 35 1998 381 387
83. E. Wyrzykiewicz, and A. Blaszczyk New isomeric N-substituted hydrazones of 2-, 3-and 4-pyridinecarboxaldehydes and methyl-3-pyridylketone Journal of Heterocyclic Chemistry 37 2000 975 981
84. A.M. Municio, and A. Ribera Sintesis De 2-Hidracino- Isonicotinoilhidracida Y Su N-Oxido Anales de la Real Sociedad Española de Física y Química B 59 1963 179 184
85. M.J. Hearn, Antimycobacterial Compounds and Method for Making the Same. USA Patent n° US 6,846,933 B1, 2005.
86. A. Rieche, G. Hilgetag, C. Bischoff, and H. Mucke Die Tuberkulostatische Wirksamkeit Von Inh-Acyl-Verbindungen Archiv der Pharmazie Bericht 295 1962 707 714
87. L.I. Giannola, G. Giammona, and R. Alotta Pro-drugs of isoniazid - synthesis and diffusion characteristics of acyl derivatives Pharmazie 47 1992 423 425
88. C. Ràfols, E. Bosch, R. Ruiz, K.J. Box, M. Reis, C. Ventura, S. Santos, M.E. Araújo, and F. Martins Acidity and hydrophobicity of several new potential antitubercular drugs: isoniazid and benzimidazole derivatives Journal of Chemical & Engineering Data 57 2012 330 338
89. Y. Benadie, M. Deysel, D.G.R. Siko, V.V. Roberts, S. Van Wyngaardt, S.T. Thanyani, G. Sekanka, A.M.C. Ten Bokum, L.A. Collett, J. Grooten, M.S. Baird, and J.A. Verschoor Cholesteroid nature of free mycolic acids from M. tuberculosis Chemistry and Physics of Lipids 152 2008 95 103
90. M. Hall, E. Frank, G. Holmes, B. Pfahringer, P. Reutemann, and I.H. Witten The WEKA data mining software: an update SIGKDD Explorations 11 2009 10 18
91. A. Verloop, and J. Tipker Pharmaco chemistry library D. Hadzi, B. Jorman-Blazic, QSAR in Drug Design and Toxicology 1987 Elsevier Science Publishers BV Amsterdam 97 125
92. R.P. Verma, A. Kurup, S.B. Mekapati, and C. Hansch Chemical-biological interactions in human Bioorganic & Medicinal Chemistry 13 2005 933 948 (Pubitemid 40164580)
93. C.E. Barry, R.A. Slayden, A.E. Sampson, and R.E. Lee Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs Biochemical Pharmacology 59 2000 221 231 (Pubitemid 30001748)
94. T. Scior, and S.J. Garces-Eisele Isoniazid is not a lead compound for its pyridyl ring derivatives, isonicotinoyl amides, hydrazides, and hydrazones: a critical review Current Medicinal Chemistry 13 2006 2205 2219 (Pubitemid 44132610)
95. A. Punkvang, P. Saparpakorn, S. Hannongbua, P. Wolschann, A. Beyer, and P. Pungpo Investigating the structural basis of arylamides to improve potency against M. tuberculosis strain through molecular dynamics simulations European Journal of Medicinal Chemistry 45 2010 5585 5593
96. http://www.organic-chemistry.org/prog/peo/.
97. A.M. Matos, M. Reis, V. Miranda, L. Santos, S. Santos, F. Martins, C. Ventura, and M.S. Santos Lipophilicity of some active Mycobacterium tuberculosis isoniazid derivatives: a comparative study between octanol-water (log Po/w) and micelle-water (log Kp) partition coefficients Abstracts of the XXII International Symposium on Medicinal Chemistry, Berlin, Germany, 2012 2012 ChemMedChem Weinheim, Germany 328 Abstract P521
98. N.L. Wengenack, and F. Rusnak Evidence for isoniazid-dependent free radical generation catalyzed by Mycobacterium tuberculosis KatG and the isoniazid-resistant mutant KatG(S315T) Biochemistry-Us 40 2001 8990 8996 (Pubitemid 32709533)
99. R. Pierattelli, L. Banci, N.A.J. Eady, J. Bodiguel, J.N. Jones, P.C.E. Moody, E.L. Raven, B. Jamart-Gregoire, and K.A. Brown Enzyme-catalyzed mechanism of isoniazid activation in class I and class III peroxidases The Journal of Biological Chemistry 279 2004 39000 39009 (Pubitemid 39296061)
100. T. Deemagarn, X. Carpena, R. Singh, B. Wiseman, I. Fita, and P.C. Loewen Structural characterization of the Ser324Thr variant of the catalase-peroxidase (KatG) from Burkholderia pseudomallei Journal of Molecular Biology 345 2005 21 28 (Pubitemid 39572822)
101. X.B. Zhao, H. Yu, S.W. Yu, F. Wang, J.C. Sacchettini, and R.S. Magliozzo Hydrogen peroxide-mediated isoniazid activation catalyzed by Mycobacterium tuberculosis catalase-peroxidase (KatG) and its S315T mutant Biochemistry-Us 45 2006 4131 4140
102. X.B. Zhao, S.W. Yu, and R.S. Magliozzo Characterization of the binding of isoniazid and analogues to Mycobacterium tuberculosis catalase-peroxidase Biochemistry-Us 46 2007 3161 3170 (Pubitemid 46449138)
103. N.L. Wengenack, S. Todorovic, L. Yu, and F. Rusnak Evidence for differential binding of isoniazid by Mycobacterium tuberculosis KatG and the isoniazid-resistant mutant KatG(S315T) Biochemistry-Us 37 1998 15825 15834 (Pubitemid 28524754)
104. B. Heym, P.M. Alzari, N. Honore, and S.T. Cole Missense mutations in the catalase-peroxidase gene, Katg, are associated with isoniazid resistance in Mycobacterium tuberculosis Molecular Microbiology 15 1995 235 245
105. J.M. Musser, V. Kapur, D.L. Williams, B.N. Kreiswirth, D. vanSoolingen, and J.D.A. vanEmbden Characterization of the catalase-peroxidase gene (katG) and InhA locus in isoniazid-resistant and -susceptible strains of Mycobacterium tuberculosis by automated DNA sequencing: restricted array of mutations associated with drug resistance The Journal of Infectious Diseases 173 1996 196 202
106. R.A. Slayden, and C.E. Barry The genetics and biochemistry of isoniazid resistance in Mycobacterium tuberculosis Microbes and Infection 2 2000 659 669 (Pubitemid 30412577)
107. L. Powers, A. Hillar, and P.C. Loewen Active site structure of the catalase-peroxidases from Mycobacterium tuberculosis and Escherichia coli by extended X-ray absorption fine structure analysis Biochimica et Biophysica Acta 1546 2001 44 54 (Pubitemid 32217801)
108. Y.G. Jin, S.F. Chen, R. Xin, and Y.S. Zhou Monolayers of the lipid derivatives of isoniazid at the air/water interface and the formation of self-assembled nanostructures in water Colloid Surface B 64 2008 229 235
109. S.W. Yu, S. Girotto, C. Lee, and R.S. Magliozzo Reduced affinity for isoniazid in the S315T mutant of Mycobacterium tuberculosis KatG is a key factor in antibiotic resistance The Journal of Biological Chemistry 278 2003 14769 14775 (Pubitemid 36799801)
110. K.E. Dooley, C.D. Mitnick, M.A. DeGroote, E. Obuku, V. Belitsky, C.D. Hamilton, M. Makhene, S. Shah, J.C.M. Brust, N. Durakovic, and E. Nuermberger Resist-Tb, old drugs, new purpose: retooling existing drugs for optimized treatment of resistant tuberculosis Clinical Infectious Diseases 55 2012 572 581
111. I. Orme, J. Secrist, S. Anathan, C. Kwong, J. Maddry, R. Reynolds, A. Poffenberger, M. Michael, L. Miller, J. Krahenbuh, L. Adams, A. Biswas, S. Franzblau, D. Rouse, D. Winfield, J. Brooks, and T.D.S. Progra Search for new drugs for treatment of tuberculosis Antimicrobial Agents and Chemotherapy 45 2001 1943 1946 (Pubitemid 32591680)
112. F.R. Pavan, P.I.D. Maia, S.R.A. Leite, V.M. Deflon, A.A. Batista, D.N. Sato, S.G. Franzblau, and C.Q.F. Leite Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity European Journal of Medicinal Chemistry 45 2010 1898 1905
113. W. Vonsassen, M. Castroparra, E. Musch, and M. Eichelbaum Determination of isoniazid, acetylisoniazide, acetylhydrazine and diacetylhydrazine in biological-fluids by high-performance liquid-chromatography Journal of Chromatography 338 1985 113 122 (Pubitemid 15143956)
114. G.M. Sheldrick A short history of SHELX Acta Crystallographica A 64 2008 112 122
115. L.J. Farrugia WinGX suite for small-molecule single-crystal crystallography Journal of Applied Crystallography 32 1999 837 838 (Pubitemid 129794704)
116. S. Rusch-Gerdes, G.E. Pfyffer, M. Casal, M. Chadwick, and S. Siddiqi Multicenter laboratory validation of the BACTEC MGIT 960 technique for testing susceptibilities of Mycobacterium tuberculosis to classical second-line drugs and newer antimicrobials Journal of Clinical Microbiology 44 2006 688 692
117. B. Springer, K. Lucke, R. Calligaris-Maibach, C. Ritter, and E.C. Bottger Quantitative drug susceptibility testing of Mycobacterium tuberculosis by use of MGIT 960 and EpiCenter instrumentation Journal of Clinical Microbiology 47 2009 1773 1780