Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units

Bioorganic and Medicinal Chemistry Letters

Volumn 27, Issue 23, 2017, Pages 5190-5196

  Choi, Peter J ^a   Sutherland, Hamish S ^a   Tong, Amy S T ^a   Blaser, Adrian ^a   Franzblau, Scott G ^c   Cooper, Christopher B ^d   Lotlikar, Manisha U ^d   Upton, Anna M ^d   Guillemont, Jerome ^e   Motte, Magali ^e   Queguiner, Laurence ^e   Andries, Koen ^f   Van den Broeck, Walter ^f   Denny, William A ^a,b   Palmer, Brian D ^a,b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT   (United States)

^e Janssen Laboratories   (France)

^f JANSSEN RESEARCH FOUNDATION   (Belgium)

Author keywords

Bedaquiline; Bedaquiline analogues; Drug development; Tuberculosis

Indexed keywords

BEDAQUILINE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; PYRIDINE DERIVATIVE; THIOPHENE DERIVATIVE; POTASSIUM CHANNEL HERG; QUINOLINE DERIVATIVE; TUBERCULOSTATIC AGENT;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG BIOAVAILABILITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; LIPOPHILICITY; LIVER MICROSOME; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SUZUKI REACTION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; HALF LIFE TIME; IC50; METABOLISM; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM TUBERCULOSIS; ORAL DRUG ADMINISTRATION; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ADMINISTRATION, ORAL; ANIMALS; ANTITUBERCULAR AGENTS; DIARYLQUINOLINES; ERG1 POTASSIUM CHANNEL; HALF-LIFE; HETEROCYCLIC COMPOUNDS; HUMANS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MICROSOMES, LIVER; MYCOBACTERIUM TUBERCULOSIS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85032286366     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2017.10.042     Document Type: Article

References (20)

1. Sreeramareddy, C.T., Panduru, K.V., Menten, J., Van den Ende, J., Time delays in diagnosis of pulmonary tuberculosis: a systematic review of literature. BMC Infect Dis, 9, 2009, 91.
2. World Health Organization global tuberculosis report 2016. ISBN 978 92 4 156539 4. < http://www.who.int>; Accessed August 30th 2017.
3. Koul, A.N., Dendouga, N., Vergauwen, K., et al. Diarylquinolines target subunit c of mycobacterial ATP synthase. Nat Chem Biol 3 (2007), 323–324.
4. Diacon, A.H., Donald, P.R., Pym, A., et al. Antimicrob Agents Chemother 56 (2012), 3271–3276.
5. Guillemont, J.E.G., Meyer, C., Poncelet, A., Bourdrez, X., Andries, K., Future Med Chem 3 (2011), 1345–1360.
6. Svensson, E.M., Murray, S., Karlsson, M.O., Dooley, K.E., J Antimicrob Chemother 70 (2015), 1106–1114.
7. Prescribing information for bedaquiline. Retrieved August 30th 2017. < http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf>.
8. Chen, M., Borlak, J., Tong, W., Hepatology 58 (2013), 388–396.
9. Kakkar, A.K., Dahiya, N., Tuberculosis 94 (2014), 357–362.
10. Tong, A.S.T., Choi, P.J., Blaser, A., et al. ACS Med Chem Lett 8 (2017), 1019–1024, 10.1016/j.bmc.2017.09.025.
11. Guillemont JEG, Dorange I, Motte MMS, Andries KJ, Koul A. WO 2008/068268 A1; June 2008.
12. Smith, J.A., Jones, R.K., Booker, G.W., Pyke, S.M., J Org Chem 73 (2008), 8880–8892.
13. Jung, J.-K., Johnson, B.R., Duong, T., et al. J Med Chem 50 (2007), 1445–1448.
14. Chen, X.-T., Pitis, P., Liu, G., et al. J Med Chem 56 (2013), 8019–8031.
15. Dorsch D, Schadt O, Stieber F, Blaukat, A. WO 2009143945 A1; 12 Mar 2009.
16. Collins, L.A., Franzblau, S.G., Antimicrob Agents Chemother 41 (1997), 1004–1009.
17. Cho, S.H., Warit, S., Wan, B., Hwang, C.H., Pauli, G.F., Franzblau, S.G., Antimicrob Agents Chemother 51 (2007), 1380–1385.
18. Palmer, B.D., Thompson, A.M., Sutherland, H.S., et al. J Med Chem 53 (2010), 282–294.
19. Falzari, K., Zhu, Z., Pan, D., Liu, H., Hongmanee, P., Franzblau, S.G., Antimicrob Agents Chemother 49 (2005), 1447–1454.
20. FDA briefing package on Sirturo™ (NDA 204-384). < https://wayback.archive-it.org/7993/20170405204607/https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/Anti-InfectiveDrugsAdvisoryCommittee/UCM329258.pdf>; Accessed 30th August 2017.