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

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.

SUBMITTER: Qiao CJ

PROVIDER: S-EPMC6331863 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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

Qiao Chang-Jiang CJ Wang Xiao-Kui XK Xie Fei F Zhong Wu W Li Song S

Molecules (Basel, Switzerland) 20151211 12

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 combine ...[more]

PMID: 26690407

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