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Open AccessArticle

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

by Chang-Jiang Qiao 1,2, Xiao-Kui Wang 2, Fei Xie 2, Wu Zhong 2,* and Song Li 1,2,*
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
Molecules 2015, 20(12), 22272-22285; https://doi.org/10.3390/molecules201219846
Received: 3 November 2015 / Revised: 4 December 2015 / Accepted: 7 December 2015 / Published: 11 December 2015
(This article belongs to the Section Medicinal Chemistry)
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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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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