Antitubercular drug development: Current status and research strategies

Mini-Reviews in Medicinal Chemistry

Volumn 13, Issue 11, 2013, Pages 1664-1684

  Barot, Kuldipsinh P ^a   Nikolova, Stoyanka ^b   Ivanov, Illiyan ^b   Ghate, Manjunath D ^a  

^a NIRMA UNIVERSITY   (India)

^b UNIVERSITY OF PLOVDIV   (Bulgaria)

Author keywords

Molecular targets; Novel agents in evaluation phase; Novel antitubercular agents; Novel heterocyclic molecules; Tuberculosis

Indexed keywords

6, 7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO [2, 1 B] [1, 3] OXAZINE; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; 7 (7 AMINO 7 METHYL 5 AZASPIRO [2.4] HEPTAN 5 YL) 6 FLUORO 1 (2 FLUOROCYCLOPROPYL) 1, 4 DIHYDRO 8 METHOXY 4 OXO 3 QUINOLINECARBOXYLIC ACID; 7 (7 AMINO 7 METHYL 5 AZASPIRO[2.4]HEPTAN 5 YL) 6 FLUORO 1 (2 FLUOROCYCLOPROPYL) 1,4 DIHYDRO 8 METHOXY 4 OXO 3 QUINOLINECARBOXYLIC ACID; AMINOSALICYLIC ACID; AZD 5847; BDM 31343; BEDAQUILINE; BTZ 043; CAPREOMYCIN; CYCLOSERINE; DELAMANID; DNB 1; ETHAMBUTOL; ETHIONAMIDE; GATIFLOXACIN; GOLOTIMOD; ISONIAZID; KANAMYCIN; LEVOFLOXACIN; LL 3858; LL 385843; METRONIDAZOLE; MOXIFLOXACIN; N (2 ADAMANTYL) N' GERANYLETHYLENEDIAMINE; NITAZOXANIDE; OPC 6768344; PYRAZINAMIDE; RIFALAZIL; RIFAMPICIN; RIFAPENTINE; SQ 10945; SQ 609; SQ 60947; STREPTOMYCIN; SUDOTERB; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ABSENCE OF SIDE EFFECTS; ARTICLE; BACTERIAL GROWTH; DISEASE ASSOCIATION; DRUG MEGADOSE; EXTENSIVELY DRUG RESISTANT TUBERCULOSIS; GROWTH INHIBITION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MINIMUM INHIBITORY CONCENTRATION; MOLECULARLY TARGETED THERAPY; MULTIDRUG RESISTANT TUBERCULOSIS; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PHASE 3 CLINICAL TRIAL (TOPIC); PHYSICAL CHEMISTRY; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS; UNSPECIFIED SIDE EFFECT;

ANTITUBERCULAR AGENTS; CLINICAL TRIALS AS TOPIC; CYTOCHROME P-450 ENZYME SYSTEM; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE, MULTIPLE, BACTERIAL; HETEROCYCLIC COMPOUNDS; HUMANS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84888020621     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/13895575113139990076     Document Type: Article

References (132)

1. World Health Organization, Global Tuberculosis Control, 2011, ISBN 978 92 4 1564380.
2. Nuermberger, E.; Grosset, J. Pharmacokinetic and pharmacodynamic issues in the treatment of mycobacterial infections. Eur. J. Clin. Microbiol. Infect. Dis, 2005, 23, 243-255.
3. Moran, N. WHO issues another gloomy tuberculosis report. Nat. Med, 1996, 2, 377.
4. De Blic, J. Tuberculosis, a worldwide urgency. Arch. Pediatr, 2005, 2, 73.
5. Farmer, P.; Bayona, J.; Beccera, M.; Furin, J.; Henry, C.; Hiarr, H.; Kim, J. Y.; Nardell, E.; Shin, S. The dilemma of MDR-TB in the global era. Int. J. Tuberc. Lung Dis, 1998, 2, 869-876.
6. Turenne, C. Y.; Tschetter, L.; Wolfe, J.; Kabani, A. Necessity of quality-controlled 16S rRNA gene sequence databases: identifying nontuberculous Mycobacterium species. J. Clin. Microbiol, 2001, 39, 3637-3648.
7. Dover. L. G.; Coxon, G. D. Current status and research strategies in tuberculosis drug development. J. Med. Chem, 2011, 54, 6157-6165.
8. Collins, K. R.; Quinones-Mateu, M. E.; Toossi, Z.; Arts, E. J. Impact of tuberculosis on HIV-1 replication, diversity, and disease progression. AIDS Rev, 2002, 4, 165-176.
9. Cardona, P. J.; Ruiz-Manzano, J. On the nature of Mycobacterium tuberculosis-latent bacilli. Eur. Respir. J, 2004, 24, 1044-1051.
10. Wayne, L. G. Dormancy of Mycobacterium tuberculosis and latency of disease. Eur. J. Clin. Microbiol. Infect. Dis, 1994, 13, 908-914.
11. Villemagne, B.; Crauste, C.; Flipo, M.; Baulard, A. R.; Déprez, B.; Willand, N. Tuberculosis: the drug development pipeline at a glance. Eur. J. Med. Chem, 2012, 51, 1-16.
12. Dye, C.; Williams, B. G. The population dynamics and control of tuberculosis. Science, 2010, 328, 856-861.
13. Zhang, Y. The magic bullets and tuberculosis drug targets. Annu. Rev. Pharmacol. Toxicol, 2005, 45, 529-564.
14. Garcia, A. B.; Palacios, J. J.; Ruiz, M. J.; Barluenga, J.; Aznar, F.; Cabal, M. P.; Garcia, J. M.; Diaz, N. Strong in vitro activities of two new rifabutin analogs against multidrug-resistant Mycobacterium tuberculosis. Antimicrob. Agents Chemother, 2010, 54, 5363-5365.
15. Koul, A.; Arnoult, E.; Lounis, N.; Guillemont, J.; Andries, K. The challenge of new drug discovery for tuberculosis. Nature, 2011, 469, 483-490.
16. Siddiqi, M. I.; Kumar, A. Review of knowledge for rational design and identification of anti tubercular compounds. Expert Opin. Drug Dis, 2009, 4, 1005-1015.
17. Cole, S. T.; Phillip, W.; Heym, B. Mechanisms of drug resistance in Mycobacterium tuberculosis. Curr. Top. Microbiol. Immunol, 1996, 215, 49-69.
18. Peirs, P.; De Wit, L.; Braibant, M.; Huygen, K. A serine/threonine protein kinase from Mycobacterium tuberculosis. Eur. J. Biochem, 1997, 244, 604-612.
19. Sakaya, S. M.; Contreras, M. S.; Dirlam, J. P.; Connell, O.; Hayashi, S. F.; Santoro, S. L.; Kamicker, B. J. Synthesis and structure-activity relationships of thiotetronic acid analogues of thiolactomycin. Bioorg. Med. Chem. Lett, 2001, 11, 2751-2754.
20. Keil, J. G.; Godfrey, J. C.; Cron, M. J.; Hooper, I. R.; Nettleton, D. E.; Price, K. E.; Schmitz, H. Structure-activity relationships in chemically modified coumermycin. Pure Appl. Chem, 1971, 28, 571-601.
21. Ducati, R. G. The resumption of consumption-a review on tuberculosis. Tuber. Review, 2006, 101, 697-714.
22. Kremer, L.; Besra, G. S. Re-emergence of tuberculosis: strategies and treatment. Expert Opin. Investig. Drugs, 2002, 11, 153-157.
23. Rosas Taraco, A. G. Mycobacterium tuberculosis upregulates coreceptors CCR5 and CXCR4 while HIV modulates CD14 favoring concurrent infection. AIDS Res. Hum. Retroviruses, 2006, 22, 45-51.
24. Goletti, D. Effect of Mycobacterium tuberculosis on HIV replication. Role of immune activation. J. Immunol, 1996, 157, 1271-1278.
25. Protopopova, M.; Hanrahan, C.; Nikonenko, B.; Samala, R.; Chen, P.; Gearhart, J.; Einck, L.; Nacy, C. A. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1, 2-ethylenediamines. J. Antimicrob. Chemother, 2005, 56, 968-974.
26. Boshoff, H. I.; Mariani, F. The transcriptional responses of Mycobacterium tuberculosis to inhibitors of metabolism: novel insights into drug mechanisms of action. J. Biol. Chem, 2004, 279, 40174-40184.
27. Nikonenko, B. V.; Protopopova, M.; Samala, R.; Einck, L.; Nacy, C. A. Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs. Antimicrob. Agents Chemother, 2007, 51, 1563-1565.
28. Ashtekar, D. R.; Costa-Perira, R.; Nagrajan, K.; Vishvanathan, N.; Bhatt, A. D.; Rittel, W. In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. Antimicrob. Agents Chemother, 1993, 37, 183-186.
29. Stover, C. K.; Warrener, P.; VanDevanter, D. R.; Sherman, D. R.; Arain, T. M.; Langhorne, M. H.; Anderson, S. W.; Towell, J. A. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature, 2000, 405, 962-966.
30. Barry, C. E.; Boshoff, H. I.; Dowd, C. S. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr. Pharm. Des, 2004, 10, 3239-3262.
31. Manjunatha, U. H.; Boshoff, H.; Dowd, C. S.; Zhang, L.; Albert, T. J.; Norton, J. E. Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U. S. A, 2005, 103, 431-436.
32. Sasaki, H.; Haraguchi, Y.; Itotani, M.; Kuroda, H.; Hashizume, H.; Tomishige, T. Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2, 3-dihydroimidazo[2, 1-b]oxazoles. J. Med. Chem, 2006, 49, 7854-7860.
33. 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.
34. Huitric, E.; Verhasselt, P.; Andries, K.; Hoffner, S. E. In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor. Antimicrob. Agents Chemother, 2007, 51, 4202-4204.
35. Pfyffer, G. E.; Auckenthaler, R.; Van Embden, J. D.; Van Soolingen, D. Mycobacterium canettii, the smooth variant of M. tuberculosis, isolated from a Swiss patient exposed in Africa. Emerg. Infect. Dis, 1998, 4, 631-4.
36. Lenaerts, A. J.; Gruppo, V.; Marietta, K. S.; Johnson, C. M.; Driscoll, D. K.; Tompkins, N. M. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models. Antimicrob. Agents Chemother, 2005, 49, 2294-2301.
37. Nantermet, G.; Barrow, J. C.; Lindsley, S. R.; Young, M.; Mao, S.; Carroll, S. Imidazole acetic acid TAFIa inhibitors: SAR studies centered around the basic P(1)(') group. Bioorg. Med. Chem. Lett, 2004, 14, 2141-2145.
38. Nakamura, T.; Kakinuma, H.; Umemiya, H; Amada, H.; Miyata, N. Imidazole derivatives as new potent and selective 20-HETE synthase inhibitors. Bioorg. Med. Chem. Lett, 2004, 14, 333-336.
39. Roman, G.; Riley, J. G.; Vlahakis, J. Z.; Kinobe, R. T.; Brien, F. Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: effect of halogen substitution in the phenyl ring. Bioorg. Med. Chem, 2007, 15, 3225-3234.
40. Su Han, M.; Kim, D. H. Effect of zinc ion on the inhibition of carboxypeptidase A by imidazole-bearing substrate analogues. Bioorg. Med. Chem. Lett, 2001, 11, 1425-1427.
41. Silva, G. A.; Costa, L. M. M.; Brito, F. C. F.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorg. Med. Chem, 2004, 12, 3149-3158.
42. Savini, L.; Chiasserini, L.; Travagli, V.; Pellerano, C.; Novellino, E.; Consentino, S.; Pisano, M. B. New alpha-(N)-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur. J. Med. Chem, 2004, 39, 113-122.
43. Abdel Aziz, H. A.; Mekawey, A. A. I.; Dawood, K. M. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur. J. Med. Chem, 2009, 44, 3637-3644.
44. Bekhit, A. A.; Hymete, A.; El-Din, A.; Bekhit, A.; Damtew, A.; Aboul-Enein, H. Y. Pyrazoles as promising scaffold for the synthesis of anti-inflammatory and/or antimicrobial agent: a review. Mini. Rev. Med. Chem, 2010, 10, 1014-1033.
45. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. A new series of PDGF receptor tyrosine kinase inhibitors: 3-substituted quinoline derivatives. J. Med. Chem, 1994, 37, 2129-2137.
46. Aguinaldo, V. M.; Dalangin Mallari, A. P.; Macabeo, L.; Byrne, F.; Abe, T.; Yamauchi, S. G.; Franzblau, N. Quinoline alkaloids from Lunasia amara inhibit Mycobacterium tuberculosis H37Rv in vitro. Int. J. Antimicrob. Agents, 2007, 29, 45-47.
47. Lamichhane, G.; Zignol M, Blades NJ, Geiman DE, Dougherty A, Grosset J, Broman KW, Bishai WR. A postgenomic method for predicting essential genes at subsaturation levels of mutagenesis: application to Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U. S. A, 2003, 100, 7213-7218.
48. Sassetti, C. M. Genes required for mycobacterial growth defined by high density mutagenesis. Mol. Microbiol, 2003, 48, 77-84.
49. Sassetti, C. M.; Rubin, E. J. Genetic requirements for mycobacterial survival during infection. Proc. Natl. Acad. Sci. U. S. A, 2003, 100, 12989-12994.
50. McKinney, J. D.; Hönerzu Bentrup, K.; Muñoz-Elías, E. J.; Miczak, A.; Chen, B.; Chan, W. T. Persistence of Mycobacterium tuberculosis in macrophages and mice requires the glyoxylate shunt enzyme isocitrate lyase. Nature, 2000, 406, 735-738.
51. Park, H. D.; Guinn, K. M.; Harrell, M. I.; Liao, R.; Voskuil, M. I.; Tompa, M. Rv3133c/dosR is a transcription factor that mediates the hypoxic response of Mycobacterium tuberculosis. Mol. Microbiol, 2003, 48, 833-843.
52. Gerdes, K.; Christensen, S. K.; Løbner-Olesen, A. Prokaryotic toxin-antitoxin stress response loci. Nat. Rev. Microbiol, 2005, 3, 371-382.
53. Engelberg-Kulka, H; Sat, B.; Reches, M.; Amitai, S.; Hazan, R. Bacterial programmed cell death systems as targets for antibiotics. Trends Microbiol, 2004, 12, 66-71.
54. Ujjinamatada, R. K.; Baier, A.; Borowski, P.; Hosmane, R. S. An analogue of AICAR with dual inhibitory activity against WNV and HCV NTPase/helicase: synthesis and in vitro screening of 4-carbamoyl-5-(4, 6-diamino-2, 5-dihydro-1, 3, 5-triazin-2-yl)imidazole-1-beta-D-ribofuranoside. Bioorg. Med. Chem. Lett, 2007, 17, 2285-2288.
55. Zhang, Y.; Wade, M. M.; Scorpio, A.; Zhang, H.; Sun, Z. Mode of action of pyrazinamide: disruption of Mycobacterium tuberculosis membrane transport and energetics by pyrazinoic acid. J. Antimicrob. Chemother, 2003, 52, 790-795.
56. Zhang, Y.; Scorpio, A.; Nikaido, H.; Sun, Z. Role of acid pH and deficient efflux of pyrazinoic acid in unique susceptibility of Mycobacterium tuberculosis to pyrazinamide. J. Bacteriol, 1999, 181, 2044-2049.
57. Zhang, Y. The magic bullets and tuberculosis drug targets. Annu. Rev. Pharmacol. Toxicol, 2005, 45, 529-564.
58. Mitchison, D. A. The search for new sterilizing anti-tuberculosis drugs. Front. Biosci, 2004, 9, 1059-1072.
59. Butcher, E. C.; Berg, E. L.; Kunkel, E. J. Systems biology in drug discovery. Nat. Biotechnol, 2004, 22, 1253-1259.
60. Borisy, A. A.; Elliott, P. J.; Hurst, N. W.; Lee, M. S.; Lehar, J.; Price, E. R. Systematic discovery of multicomponent therapeutics. Proc. Natl. Acad. Sci. U. S. A, 2003, 100, 7977-7982.
61. Donald, P. R. The assessment of new anti-tuberculosis drugs for a paediatric indication. Int. J. Tuberc. Lung D, 2007, 11, 1162-1165.
62. Donald, P. R.; Schaaf, H. S. Old and new drugs for the treatment of tuberculosis in children. Paediatr. Respir. Rev, 2007, 8, 134-141.
63. Andries, K.; Verhasselt, P.; Guillemont, J.; Gohlmann, H. W.; Neefs, J. M.; Winkler, H.; Van Gestel, J.; Timmerman, P.; Zhu, M.; Lee, E.; Williams, P. A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis. Science, 2005, 307, 223-227.
64. Stover, C. K.; Warrener, P.; VanDevanter, D. R.; Sherman, D. R.; Arain, T. M.; Langhorne, M. H.; Anderson, S. W.; Towell, J. A.; Yuan, Y. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature, 2000, 405, 962-966.
65. Jia, L.; Tomaszewski, J. E.; Hanrahan, C.; Coward, L.; Noker, P.; Gorman, G.; Nikonenko, B.; Protopopova, M. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br. J. Pharmacol, 2005, 144, 80-87.
66. Matsumoto, M.; Hashizume, H.; Tomishige, T.; Kawasaki, M.; Tsubouchi, H.; Sasaki, H.; Shimokawa, Y.; Komatsu, M. OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med, 2006, 3, 466.
67. Amaral, L.; Boeree, M. J.; Gillespie, S. H.; Udwadia, Z. F.; Van Soolingen, D. Thioridazine cures extensively drug-resistant tuberculosis (XDR-TB) and the need for global trials is now! Int. J. Antimicrob. Agents, 2010, 35, 524-526.
68. Bogatcheva, E.; Hanrahan, C.; Nikonenko, B.; Santos, G. D. I.; Reddy, V.; Chen, P.; Barbosa, F.; Einck, L.; Nacy, C.; Protopopova, M. Identification of SQ609 as a lead compound from a library of dipiperidines. Bioorg. Med. Chem. Lett, 2011, 7, 15.
69. Koga, T.; Fukuoka, T.; Doi, N.; Harasaki, T.; Inoue, H.; Hotoda, H.; Kakuta, M.; Muramatsu, Y.; Yamamura, N.; Hoshi, M.; Hirota, T. Activity of capuramycin analogues against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium intracellulare in vitro and in vivo. J. Antimicrob. Chemother, 2004, 54, 755-760.
70. De Carvalho, L. P.; Lin, G.; Jiang, X.; Nathan, C. Nitazoxanide kills replicating and nonreplicating Mycobacterium tuberculosis and evades resistance. J. Med. Chem, 2009, 52, 5789-5792.
71. Flores, A. R.; Parsons, L. M.; Pavelka, M. S. Genetic analysis of the beta-lactamases of Mycobacterium tuberculosis and Mycobacterium smegmatis and susceptibility to beta-lactam antibiotics. Microbiology, 2005, 151, 521-532.
72. Hugonnet, J. E.; Tremblay, L. W.; Boshoff, H. I. Meropenemclavulanate is effective against extensively drug-resistant Mycobacterium tuberculosis. Science, 2009, 323, 1215-1218.
73. Makarov, V.; Manina, G.; Mikusova, K.; Mollmann, U.; Ryabova, O.; Saint-Joanis, B.; Dhar, N.; Pasca, M. R.; Buroni, S.; Lucarelli, A. P. Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis. Science, 2009, 324, 801-804.
74. Al-Balas, Q.; Anthony, N. G.; Al-Jaidi, B.; Alnimr, A.; Abbott, G.; Brown, A. K.; Taylor, R. C.; Besra, G. S. Identification of 2-aminothiazole-4-carboxylate derivatives active against Mycobacterium tuberculosis H37Rv and the beta-ketoacyl-ACP synthase mtFabH. PloS One, 2009, 4, 5617.
75. Ananthan, S.; Faaleolea, E. R.; Goldman, R. C.; Hobrath, J. V.; Kwong, C. D.; Laughon, B. E.; Maddry, J. A.; Mehta, A.; Rasmussen, L. High-throughput screening for inhibitors of Mycobacterium tuberculosis H37Rv. Tuberculosis, 2009, 89, 334-353.
76. Lenaerts, A. J.; Hoff, D.; Aly, S.; Ehlers, S.; Andries, K.; Cantarero, L.; Orme, I. M.; Basaraba, R. J. Location of persisting mycobacteria in a Guinea pig model of tuberculosis revealed by r207910. Antimicrob. Agents Chemother, 2008, 51, 3338-3345.
77. Matsumoto, M.; Hashizume, H.; Tsubouchi, H.; Sasaki, H.; Itotani, M.; Kuroda, H.; Tomishige, T.; Kawasaki, M.; Komatsu, M. Screening for novel antituberculosis agents that are effective against multidrug resistant tuberculosis. Curr. Top. Med. Chem, 2008, 7, 499-507.
78. Brandish, P. E.; Kimura, K. I.; Inukai, M.; Southgate, R.; Lonsdale, J. T.; Bugg, T. D. Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: inhibition of phospho-N-acetylmuramylpentapeptide translocase from Escherichia coli. Antimicrob. Agents Chemother, 1996, 40, 1640-1644.
79. Da Silva, A. D.; De Almeida, M. V.; De Souza, M. V. N. Biological activity and synthetic metodologies for the preparation of fluoroquinolones, a class of potent antibacterial agents. Curr. Med. Chem, 2003, 10, 21.
80. De Souza, M. V.; Vasconcelos, T. A.; Cardoso, S. H.; De Almeida, M. V. Fluoroquinolones: an important class of antibiotics against tuberculosis. Curr. Med. Chem, 2006, 13, 455.
81. Ema, C. R. Recent status of tuberculosis. Drug Disc. Today, 2008, 23, 13.
82. Pletz, M. W. R.; De Roux, A.; Roth, A.; Neuman, K. H.; Mauch, H.; Lode, H. Early bactericidal activity of moxifloxacin in treatment of pulmonary tuberculosis: a prospective, randomized study. Antimicrob. Agents Chemother, 2004, 48, 780.
83. Tripathi, R. P.; Tewari, N.; Dwivedi, N.; Tiwari, V. K. Fighting tuberculosis: an old disease with new challenges. Med. Res. Rev, 2005, 25, 93.
84. Sudre, P.; Ten Dam, G.; Kochi, A. Tuberculosis: a global overview of the situation today. Bull. World Health Organ, 1992, 70, 149.
85. Corbett, E. L.; Watt, C. J.; Walker, N.; Maher, D.; Williams, B. G.; Raviglione, M. C.; Dye, C. The growing burden of tuberculosis: global trends and interactions with the HIV epidemic. Arch. Intern. Med, 2003, 163, 1009-1021.
86. Koul, E.; Arnoult, N.; Lounis, J.; Guillemont, K. Adries. The challenge of new drug discovery for tuberculosis. Nature, 2011, 469, 483-489.
87. Sacchettini, J. C.; Rubin, E. J.; Freundlich, J. S. Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis. Nature Rev. Microbiol, 2008, 6, 41.
88. Schiemann, K.; Finsinger, D.; Zenke, F.; Amendt, C.; Knöchel, T.; Bruge, D.; Buchstaller, H. P.; Emde, U.; Stähle, W.; Anzali, S. The discovery and optimization of hexahydro-2H-pyrano[3, 2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5. Bioorg. Med. Chem. Lett, 2010, 20, 1491-1495.
89. Kumar, S.; Srivastava, G.; Gupta, V.; Chaturvedi, S. Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent. ACS Comb. Sci, 2011, 13, 65-71.
90. Kantevari, S.; Patpi, S. R.; Sridhar, B.; Yogeeswari, P.; Sriram, D. Synthesis and antitubercular evaluation of novel substituted aryl and thiophenyl tethered dihydro-6H-quinolin-5-ones. Bioorg. Med. Chem. Lett, 2011, 14, 1214-1217.
91. Sriram, D.; Yogeeswari, P.; Dinakaran, M.; Banerjee, D.; Bhat, P.; Gadhwal, S. Discovery of novel antitubercular 2, 10-dihydro-4aHchromeno[3, 2-c]pyridin-3-yl derivatives. Eur. J. Med. Chem, 2010, 45, 120.
92. Sriram, D.; Yogeeswari, P.; Devakaram, R. V. Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg. Med. Chem, 2006, 14, 3113-3118.
93. Eswaran, S.; Adhikari, A. V.; Chowdhury, I. H.; Pal, N. K.; Thomas, K. D. New quinoline derivatives: synthesis and investigation of antibacterial and antituberculosis properties. Eur. J. Med. Chem, 2010, 45, 3374-3383.
94. Eswaran, S.; Adhikari, A. V.; Chowdhury, I. C.; Pal, N. K. Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents. Bioorg. Med. Chem. Lett, 2010, 20, 1040-1044.
95. Dye, C.; Scheele, S.; Pathania, V. Consensus statement. Global burden of tuberculosis: estimated incidence, prevalence, and mortality by country. WHO Global Surveillance and Monitoring Project. J. Am. Med. Assoc, 1999, 282, 677-686.
96. Silva, G. A.; Costa, L. M. M.; Brito, F. C. F.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorg. Med. Chem, 2004, 12, 3149-3158.
97. Savini, L.; Chiasserini, L.; Travagli, V.; Pellerano, C.; Novellino, E.; Consentino, S.; Pisano, M. B. New alpha-(N)-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur. J. Med. Chem, 2004, 39, 113-122.
98. Abdel Aziz, H. A.; Mekawey, A. A. I.; Dawood, K. M. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur. J. Med. Chem, 2009, 44, 3637-3644.
99. Bekhit, A. A.; Hymete, A.; Damtew, A.; Aboul-Enein, H. Y. Pyrazoles as promising scaffold for the synthesis of antiinflammatory and/or antimicrobial agent: a review. Mini. Rev. Med. Chem, 2010, 10, 1014-1033.
100. Sharma, S.; Sharma, P. K.; Kumar, N.; Dudhe, R. A review on various heterocyclic moieties and their antitubercular activity. Biomed. Pharmacother, 2011, 65, 244-251.
101. Ali, M. A.; Shaharyar, M.; Siddiqui, A. A. Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives. Eur. J. Med. Chem, 2007, 42, 268-75.
102. Blair, I. A.; Timoco, R. M.; Brodie, M. J.; Clarc, R. A.; Dollery, T.; Timbrell, J. A. Plasma hydrazine concentrations in man after isoniazid and hydralazine administration. Hum Toxicol, 1985, 4, 195.
103. Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur. J. Med. Chem, 2009, 44, 4244-8.
104. Khalafi-Nezhad, A.; Rad, M. N. S.; Mohbatkar, H.; Asrari, Z.; Hemmateenejad, B. Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg. Med. Chem, 2005, 13, 1931-8.
105. Evans, B. E.; Rittle, K. E.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F. Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists. J. Med. Chem, 1998, 31, 2235-46.
106. Brændvang, M.; Gundersen, L. L. Selective anti-tubercular purines: synthesis and chemotherapeutic properties of 6-aryl-and 6-heteroaryl-9-benzylpurines. Bioorg. Med. Chem, 2005, 13, 6360-73.
107. Shindikar, A. V.; Viswanathan, C. L. Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv. Bioorg. Med. Chem. Lett, 2005, 15, 1803-6.
108. Cozarelli, N. R. Benjamin Franklin and Timothy Folger's First Printed Chart of the Gulf Stream. Science, 1980, 207, 643.
109. Tomioka, H. Prospects for development of new antimycobacterial drugs. J. Infect. Chemother, 2000, 6, 8-20.
110. Braendvang M, Bakken V, Gundersen LL. Synthesis, structure, and antimycobacterial activity of 6-[1(3H)-isobenzofuranylidenemethyl] purines and analogs. Bioorg. Med. Chem, 2009, 17, 6512-6516.
111. Ancizu, S.; Moreno, E.; Solano, B.; Villar, R.; Burguete, A.; Torres, E. New 3-methylquinoxaline-2-carboxamide 1, 4-di-Noxide derivatives as anti-Mycobacterium tuberculosis agents. Bioorg. Med. Chem, 2010, 18, 2713-9.
112. Vicente, E.; Villar, R.; Pérez-Silanes, S.; Aldana, I.; Goldman, R. C.; Mong, A. Quinoxaline 1, 4-di-N-oxide and the potential for treating tuberculosis. Infect. Disord. Drug Targets, 2011, 11, 196-204.
113. Lilienkampf, A.; Pieroni, M.; Franzblau, S. G.; Bishai, W. R.; Kozikowski, A. P. Derivatives of 3-isoxazolecarboxylic acid esters: a potent and selective compound class against replicating and nonreplicating Mycobacterium tuberculosis. Curr. Top. Med. Chem, 2012, 12, 729-34.
114. Pathak, R. B.; Chovatia, P. T.; Parekh, H. H. Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives. Bioorg. Med. Chem. Lett, 2012, 22, 5129-5133.
115. Kunes, J.; Bazant, J.; Pour, M.; Waisser, K.; Slosárek, M.; Janota, J. Quinazoline derivatives with antitubercular activity. Farmaco, 2000, 55, 725-729.
116. Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur. J. Med. Chem, 2009, 44, 4244-4248.
117. Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; De Clercq, E. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur. J. Med. Chem, 2009, 44, 2347-2353.
118. Zampieri, D.; Mamolo, M. G.; Vio, L.; Banfi, E.; Scialino, G.; Fermeglia, M. Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P450(14DM) by molecular docking and MM/PBSA method. Bioorg. Med. Chem. Lett, 2007, 15, 7444-7458.
119. Olender, D.; Zwawiak, J.; Lukianchuk, V.; Lesyk, R. Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. Eur. J. Med. Chem, 2009, 44, 645-652.
120. Puratchikodya, A.; Doble, M. Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4, 5-diphenyl-1Himidazoles. Bioorg. Med. Chem. Lett, 2007, 15, 1083-1090.
121. Achar, K. C. S.; Hosamani, K. M.; Seetharamareddy, H. R. In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. Eur. J. Med. Chem, 2010, 45, 2048-2054.
122. Gupta, P.; Hameed, S.; Jain, R. Ring-substituted imidazoles as a new class of anti-tuberculosis agents. Eur. J. Med. Chem, 2004, 39, 805-814.
123. Jyoti, P.; Vinod, T. K.; Shyam, V. S.; Vinita, C.; Bhatnagar, S.; Sinha, S. Synthesis and antitubercular screening of imidazole derivatives. Eur. J. Med. Chem, 2009, 44, 3350-3355.
124. Congiu, C.; Cocco, M. T.; Onnis, V. Design, synthesis, and in vitro antitumor activity of new 1, 4-diarylimidazole-2-ones and their 2-thione analogues. Bioorg. Med. Chem. Lett, 2008, 18, 989-993.
125. Tonelli, M.; Simone, M.; Tasso, B.; Novelli, F.; Boido, V. Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives. Bioorg. Med. Chem. Lett, 2010, 18, 2937-2953.
126. Machutta, C. A.; Bommineni, G. R.; Luckner, S. R.; Kapilashrami, K.; Ruzsicska, B.; Simmerling, C.; Kisker, C.; Tonge, J. Slow onset inhibition of bacterial beta-ketoacyl-acyl carrier protein synthases by thiolactomycin. J. Biol. Chem, 2010, 285, 6161-6169.
127. Ngo, L. T.; Okogun, J. I.; Folk, W. R. 21st century natural product research and drug development and traditional medicines. Nat. Prod. Rep, 2013, 30, 584-92.
128. Tewari, N.; Tiwari V. K.; Mishra, R. C.; Tripathi, R. P. Synthesis and bioevaluation of glycosyl ureas as alpha-glucosidase inhibitors and their effect on mycobacterium. Bioorg. Med. Chem, 2003, 11, 2911.
129. Santo, R. D.; Costi, R.; Artico, M.; Massa, S.; Lampis, G.; Deidda, D. Pyrrolnitrin and related pyrroles endowed with antibacterial activities against Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett, 1998, 8, 2931.
130. Boruwa, J.; Kalita, B.; Barua, N. C.; Borah, J. C.; Mazumder, S.; Thakur, D. Synthesis, absolute stereochemistry and molecular design of the new antifungal and antibacterial antibiotic produced by Streptomyces sp. 201. Bioorg. Med. Chem. Lett, 2004, 14, 3571.
131. Kobayashi, J.; Cheng, J. F.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T. Ascididemin, a novel pentacyclic aromatic alkaloid with potent antileukemic activity from the okinawan tunicate didemnum sp. Tetrahedron Lett, 1988, 29, 1177.
132. Sayed, K. A. E.; Bartyzel, P.; Shen, X.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Marine Natural Products as Antituberculosis Agents. Tetrahedron, 2000, 56, 949.