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Mar. Drugs 2016, 14(11), 206; doi:10.3390/md14110206

Chiral Alkyl Halides: Underexplored Motifs in Medicine

Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305, USA
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Author to whom correspondence should be addressed.
Academic Editor: Miguel O. Mitchell
Received: 24 September 2016 / Revised: 21 October 2016 / Accepted: 31 October 2016 / Published: 4 November 2016
(This article belongs to the Special Issue Marine Organohalides)
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Abstract

While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems. A number of chlorinated compounds in the pharmaceutical and food industries, as well as a growing number of halogenated marine natural products showing unique bioactivity, illustrate the role that chiral alkyl halides can play in drug discovery. Through a series of case studies, we demonstrate in this review that these motifs can indeed be stable under physiological conditions, and that halogenation can enhance bioactivity through both steric and electronic effects. Our hope is that, by placing such compounds in the minds of the chemical community, they may gain more traction in drug discovery and inspire more synthetic chemists to develop methods for selective halogenation. View Full-Text
Keywords: alkyl halide; stereochemistry; lipophilicity; anesthetic; clindamycin; corticosteroid; pimecrolimus; sucralose; halomon; lapachone; astins; forazoline alkyl halide; stereochemistry; lipophilicity; anesthetic; clindamycin; corticosteroid; pimecrolimus; sucralose; halomon; lapachone; astins; forazoline
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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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Gál, B.; Bucher, C.; Burns, N.Z. Chiral Alkyl Halides: Underexplored Motifs in Medicine. Mar. Drugs 2016, 14, 206.

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