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Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity.


ABSTRACT: Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl)piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core.

SUBMITTER: Sun D 

PROVIDER: S-EPMC2756498 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity.

Sun Dianqing D   Scherman Michael S MS   Jones Victoria V   Hurdle Julian G JG   Woolhiser Lisa K LK   Knudson Susan E SE   Lenaerts Anne J AJ   Slayden Richard A RA   McNeil Michael R MR   Lee Richard E RE  

Bioorganic & medicinal chemistry 20090409 10


Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl)piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropy  ...[more]

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