Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation

Organic and Biomolecular Chemistry

Volumn 13, Issue 12, 2015, Pages 3610-3624

  Munagala, Gurunadham ^a,b   Yempalla, Kushalava Reddy ^a,b   Singh, Samsher ^a,b   Sharma, Sumit ^a,b   Kalia, Nitin Pal ^a   Rajput, Vikrant Singh ^a,b   Kumar, Sunil ^a,b   Sawant, Sanghapal D ^a,b   Khan, Inshad Ali ^a,b   Vishwakarma, Ram A ^a,b   Singh, Parvinder Pal ^a,b  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

SCAFFOLDS;

ACTIVE COMPOUNDS; MEDICINAL CHEMISTRY; MYCOBACTERIUM TUBERCULOSIS; NITROIMIDAZOLES; NOVEL SERIES; RESISTANT STRAINS; STRUCTURE ACTIVITY RELATIONSHIPS; SYNERGISTIC EFFECT;

PHARMACOKINETICS;

MYCOBACTERIUM TUBERCULOSIS;

CYTOCHROME P450; ISOENZYME; OXAZOLE DERIVATIVE; TUBERCULOSTATIC AGENT;

ANIMAL; BAGG ALBINO MOUSE; CELL DEATH; CHEMISTRY; DISEASE MODEL; DRUG COMBINATION; DRUG EFFECTS; HEPG2 CELL LINE; HUMAN; INTRANASAL DRUG ADMINISTRATION; METABOLISM; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ADMINISTRATION, INTRANASAL; ANIMALS; ANTITUBERCULAR AGENTS; CELL DEATH; CYTOCHROME P-450 ENZYME SYSTEM; DISEASE MODELS, ANIMAL; DRUG THERAPY, COMBINATION; HEP G2 CELLS; HUMANS; ISOENZYMES; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; OXAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84925070989     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob00054h     Document Type: Article

References (34)

1. World Health Organization, Global Tuberculosis Report 2012, Technical Report from the World Health Organization, Geneva, Switzerland, 2012
2. S. Loewenberg India reports cases of totally drug-resistant tuberculosis Lancet 2012 379 205
3. D. Boccia C. A. Evans A new era for global tuberculosis control Lancet 2011 378 1293
4. K. Lonnroth, E. Jaramillo, B. Williams, C. Dye and M. Raviglione, in Tuberculosis: The Role of Risk Factors and Social Determinants, ed., E. Blas, and, A. S. Kurup, World Health Organization, WHO Press, Switzerland, 2010, p. 220
5. World Health Organization (WHO), Treatment of tuberculosis: Guidelines for national programmes, WHO Press, Geneva, Switzerland, 4th edn, 2009
6. C. E. Barry H. I. Boshoff C. S. Dowd Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis Curr. Pharm. Des. 2004 10 3239
7. L. G. Wayne H. A. Sramek Metronidazole is bactericidal to dormant cells of Mycobacterium tuberculosis Antimicrob. Agents Chemother. 1994 38 2054
8. K. Nagarajan R. G. Shankar S. Rajappa S. J. Shenoy R. Costa-Pereira Nitroimidazole XXI 2,3-dihtdro-6-nitroimidazo [2,1-b] oxazoles with antitubercular activity Eur. J. Med. Chem. 1989 24 631
9. D. R. Ashtekar R. Costa-Perira K. Nagrajan N. Vishvanathan A. D. Bhatt W. Rittel In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis Antimicrob. Agents Chemother. 1993 37 183
10. C. K. Stover P. Warrener D. R. VanDevanter D. R. Sherman T. M. Arain M. H. Langhorne S. W. Anderson J. A. Towell Y. Yuan D. N. McMurray B. N. Kreiswirth C. E. Barry W. R. Baker A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis Nature 2000 405 962
11. W. A. Denny B. D. Palmer The nitroimidazooxazines (PA-824 and analogs): structure-activity relationship and mechanistic studies Future Med. Chem. 2010 2 1295
12. H. Sasaki Y. Haraguchi M. Itotani H. Kuroda H. Hashizume T. Tomishige M. Kawasaki M. Matsumoto M. Komatsu H. Tsubouchi 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
13. M. Matsumoto H. Hashizume T. Tomishige M. Kawasaki H. Tsubouchi H. Sasaki Y. Shimokawa M. Komatsu OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice PLoS Med. 2006 3 466
14. N. J. Ryan J. H. Lo Delamanid: first global approval Drugs 2014 74 1041
15. Drug Discovery & Development. EMA Recommends Two New Tuberculosis treatments. November 22, 2013
16. C. E. Barry D. C. Crick M. R. McNeil Targeting the formation of the cell wall core of M. tuberculosis Infect. Disord.: Drug Targets 2007 7 182
17. E. C. Rivers R. L. Mancera New anti-tuberculosis drugs with novel mechanisms of action Curr. Med. Chem. 2008 15 1956
18. I. Kmentova H. S. Sutherland B. D. Palmer A. Blaser S. G. Franzblau B. Wan Y. Wang Z. Ma W. A. Denny A. M. Thompson Synthesis and Structure-Activity Relationships of Aza- and Diazabiphenyl Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6, 7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824) J. Med. Chem. 2010 53 8421
19. A. M. Thompson H. S. Sutherland B. D. Palmer I. Kmentova A. Blaser S. G. Franzblau B. Wan Y. Wang Z. Ma W. A. Denny Synthesis and Structure-Activity Relationships of Varied Ether Linker Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo-[2,1-b][1,3]oxazine (PA-824) J. Med. Chem. 2011 54 6563
20. B. D. Palmer A. M. Thompson H. S. Sutherland A. Blaser I. Kmentova S. G. Franzblau B. Wan Y. Wang Z. Ma W. A. Denny Synthesis and structure-activity studies of biphenyl analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2, 1-b][1,3]oxazine (PA-824) J. Med. Chem. 2010 53 282
21. H. S. Sutherland A. Blaser I. Kmentova S. G. Franzblau B. Wan Y. Wang Z. Ma B. D. Palmer W. A. Denny A. Thompson Synthesis and Structure-activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains J. Med. Chem. 2010 53 855
22. P. Kim L. Zhang U. H. Manjunatha R. Singh S. Patel J. Jiricek T. H. Keller H. I. Boshoff C. E. Barry III C. S. Dowd Structure-activity relationships of antitubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles J. Med. Chem. 2009 52 1317
23. P. Kim S. Kang H. I. Boshoff J. Jiricek M. Collins R. Singh U. H. Manjunatha P. Niyomrattanakit L. Zhang M. Goodwin T. Dick T. H. Keller C. S. Dowd C. E. Barry III Structure activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships J. Med. Chem. 2009 52 1329
24. V. Sudarsanam K. Nagarajan T. George S. J. Shenoy V. V. Iyer A. P. Kaulgud Nitroimidazoles: Part XI-Some Halonitro & Dinitroimidazoles Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1982 21 1022
25. 37Rv (ATCC 27294) Strain J. Med. Chem. 2011 54 5988
26. F. Himo T. Lovell R. Hilgraf V. V. Rostovtsev L. Noodleman K. B. Sharpless V. V. Fokin Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates J. Am. Chem. Soc. 2005 127 210
27. S. Sharma M. Kumar S. Sharma A. Nargotra S. Koul I. A. Khan Piperine as an inhibitor of Rv1258c, a putative multidrug efflux pump of Mycobacterium tuberculosis J. Antimicrob. Chemother. 2010 65 1694
28. C. Sala N. Dhar R. C. Hartkoorn M. Zhang Y. H. Ha P. Schneider S. T. Cole Simple model for testing drugs against nonreplicating Mycobacterium tuberculosis Antimicrob. Agents Chemother. 2010 54 4150
29. M. Zhang C. Sala R. C. Hartkoorn N. Dhar A. F. Losana S. T. Cole Streptomycin -starved Mycobacterium tuberculosis 18b, a drug discovery tool for latent tuberculosis Antimicrob. Agents Chemother. 2012 56 4150
30. A. M. Upton S. Cho T. J. Yang Y. Kim Y. Wang Y. Lu B. Wang J. Xu K. Mdluli Z. Ma S. G. Franzblau In vitro and in vivo activity against M. tuberculosis of the nitroimidazole TBA-354 Antimicrob. Agents Chemother. 2015 59 136
31. th ICAAC, 2006
32. B. D. Rakesh D. F. Bruhn M. S. Scherman L. K. Woolhiser D. B. Madhura M. Maddox A. P. Singh R. B. Lee J. G. Hurdle M. R. McNeil A. J. Lenaerts B. Meibohm R. E. Lee Pentacyclic Nitrofurans withIn Vivo Efficacy and Activity against Non replicating Mycobacterium tuberculosis PLoS One 2014 9 1
33. W. C. Dorsey P. B. Tchounwou D. Sutton Mitogenic and cytotoxic effects of pentachlorophenol to AML 12 mouse hepatocytes Int. J. Environ. Res. Public Health 2004 1 100
34. C. L. Crespi V. P. Miller B. W. Penman Microplate plate assays for inhibition of human drug metabolizing cytochrome P450 Anal. Biochem. 1997 248 188