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Molecules 2015, 20(12), 22272-22285; doi:10.3390/molecules201219846

Asymmetric Synthesis and Absolute Configuration Assignment of a New Type of Bedaquiline Analogue

1
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016, China
2
Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, 27 Taiping Road, Beijing 100850, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 3 November 2015 / Revised: 4 December 2015 / Accepted: 7 December 2015 / Published: 11 December 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [2003 KB, uploaded 11 December 2015]   |  

Abstract

Bedaquiline is the first FDA-approved new chemical entity to fight multidrug-resistant tuberculosis in the last forty years. Our group replaced the quinoline ring with a naphthalene ring, leading to a new type of triarylbutanol skeleton. An asymmetric synthetic route was established for our bedaquiline analogues, and the goal of assigning their absolute configurations was achieved by comparison of experimental and calculated electronic circular dichroism spectra, and was confirmed by the combined use of circular dichroism and NMR spectroscopy. View Full-Text
Keywords: antituberculosis; asymmetric synthesis; bedaquiline analogues; absolute configuration assignment antituberculosis; asymmetric synthesis; bedaquiline analogues; absolute configuration assignment
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Qiao, C.-J.; Wang, X.-K.; Xie, F.; Zhong, W.; Li, S. Asymmetric Synthesis and Absolute Configuration Assignment of a New Type of Bedaquiline Analogue. Molecules 2015, 20, 22272-22285.

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