Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents

ACS Medicinal Chemistry Letters

Volumn 6, Issue 10, 2015, Pages 1059-1064

  Yempalla, Kushalava Reddy ^a,b   Munagala, Gurunadham ^a,b   Singh, Samsher ^a,b   Kour, Gurleen ^a,b   Sharma, Shweta ^a   Chib, Reena ^a,b   Kumar, Sunil ^a,b   Wazir, Priya ^a   Singh, G D ^a   Raina, Sushil ^a   Bharate, Sonali S ^a   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

6 nitro 2,3 dihydroimidazooxazole; MTB H37Rv; multidrug resistant TB; Mycobacterium tuberculosis; structure activity relationship

Indexed keywords

4 AMINOPHENOL; DELAMANID; ISOTHIOCYANIC ACID DERIVATIVE; LEAD; NITROIMIDAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PHENYL ISOCYANATE; RIFAMPICIN; TUBERCULOSTATIC AGENT;

AGAR DILUTION; ANIMAL CELL; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BACTERIAL GROWTH; BACTERIAL LOAD; COLONY FORMING UNIT; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; HEPG2 CELL LINE; IN VITRO STUDY; IN VIVO STUDY; INFECTION; LIVER MICROSOME; MAXIMUM PLASMA CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PH; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; TREATMENT DURATION; VOLUME OF DISTRIBUTION;

EID: 84943806342     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00202     Document Type: Article

References (22)

1. Ditiu, L. A new era for global tuberculosis control Lancet 2011, 378, 1293 10.1016/S0140-6736(11)61567-5
2. Zumla, A.; Nahid, P.; Cole, S. T. Advances in the development of new tuberculosis drugs and treatment regimens Nat. Rev. Drug Discovery 2013, 12, 388-404 10.1038/nrd4001
3. Barry, C. E., 3rd; 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 10.2174/1381612043383214
4. 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, 2131-2144 10.1371/journal.pmed.0030466
5. Sasaki, H.; Haraguchi, Y.; Itotani, M.; Kuroda, H.; Hashizume, H.; Tomishige, T.; Kawasaki, M.; Matsumoto, M.; Komatsu, M.; Tsubouchi, H. 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 10.1021/jm060957y
6. Ryan, N. J.; Lo, J. H. Delamanid: first global approval Drugs 2014, 74, 1041-1045 10.1007/s40265-014-0241-5
7. 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.; McMurray, D. N.; Kreiswirth, B. N.; Barry, C. E.; Baker, W. R. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis Nature 2000, 405, 962-966 10.1038/35016103
8. Upton, A. M.; Cho, S.; Yang, T. J.; Kim, Y.; Wang, Y.; Lu, Y.; Wang, B.; Xu, J.; Mdluli, K.; Ma, Z.; Franzblau, S. G. In vitro and in vivo activities of the nitroimidazole TBA-354 against Mycobacterium tuberculosis Antimicrob. Agents Chemother. 2015, 59, 136-144 10.1128/AAC.03823-14
9. TB alliance drug, TBA-354, enters phase-I clinical trials, 2015. http://www.newtbdrugs.org/blog/tb-alliance-drugtba-354-enters-phase-i-clinical-trials/
10. Barry, C. E.; Crick, D. C.; McNeil, M. R. Targeting the formation of the cell wall core of M. tuberculosis Infect. Disord.: Drug Targets 2007, 7, 182-202 10.2174/187152607781001808
11. Rivers, E. C.; Mancera, R. L. New anti-tuberculosis drugs with novel mechanisms of action Curr. Med. Chem. 2008, 15, 1956-1967 10.2174/092986708785132906
12. Kmentova, I.; Sutherland, H. S.; Palmer, B. D.; Blaser, A.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A.; Thompson, A. M. 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, 8421-8439 10.1021/jm101288t
13. Lakshminarayana, S. B.; Boshoff, H. I.; Cherian, J.; Ravindran, S.; Goh, A.; Jiricek, J.; Nanjundappa, M.; Nayyar, A.; Gurumurthy, M.; Singh, R.; Dick, T.; Blasco, F.; Barry, C. E., 3rd; Ho, P. C.; Manjunatha, U. H. Pharmacokinetics-pharmacodynamics analysis of bicyclic 4-nitroimidazole analogs in a murine model of tuberculosis PLoS One 2014, 9, e105222 10.1371/journal.pone.0105222
14. Kmentova, I.; Sutherland, H. S.; Palmer, B. D.; Blaser, A.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A.; Thompson, A. M. 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, 8421-8439 10.1021/jm101288t
15. Palmer, B. D.; Thompson, A. M.; Sutherland, H. S.; Blaser, A.; Kmentova, I.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A. 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, 282-294 10.1021/jm901207n
16. Sutherland, H. S.; Blaser, A.; Kmentova, I.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Palmer, B. D.; Denny, W. A.; Thompson, A. M. Synthesis and structure-activity relationships of antitubercular 2-nitroimidazooxazines bearing heterocyclic side chains J. Med. Chem. 2010, 53, 855-866 10.1021/jm901378u
17. Thompson, A. M.; Sutherland, H. S.; Palmer, B. D.; Kmentova, I.; Blaser, A.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A. 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, 6563-6585 10.1021/jm200377r
18. Kim, P.; Kang, S.; Boshoff, H. I.; Jiricek, J.; Collins, M.; Singh, R.; Manjunatha, U. H.; Niyomrattanakit, P.; Zhang, L.; Goodwin, M.; Dick, T.; Keller, T. H.; Dowd, C. S.; Barry, C. E., 3rd Structure-activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships J. Med. Chem. 2009, 52, 1329-1344 10.1021/jm801374t
19. Kim, P.; Zhang, L.; Manjunatha, U. H.; Singh, R.; Patel, S.; Jiricek, J.; Keller, T. H.; Boshoff, H. I.; Barry, C. E., 3rd; Dowd, C. S. 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, 1317-1328 10.1021/jm801246z
20. Munagala, G.; Yempalla, K. R.; Singh, S.; Sharma, S.; Kalia, N. P.; Rajput, V. S.; Kumar, S.; Sawant, S. D.; Khan, I. A.; Vishwakarma, R. A.; Singh, P. P. 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 Org. Biomol. Chem. 2015, 13, 3610-3624 10.1039/C5OB00054H
21. McOmie, J. F. W.; Watts, M. L.; West, D. E. Demethylation of aryl methyl ethers by boron tribromide Tetrahedron 1968, 24, 2289-2292 10.1016/0040-4020(68)88130-X
22. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates J. Org. Chem. 2000, 65, 1158-1174 10.1021/jo991699y