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Design and synthesis of stereochemically defined novel spirocyclic P2-ligands for HIV-1 protease inhibitors.


ABSTRACT: The synthesis of a series of stereochemically defined spirocyclic compounds and their use as novel P2-ligands for HIV-1 protease inhibitors are described. The bicyclic core of the ligands was synthesized by an efficient nBu 3SnH-promoted radical cyclization of a 1,6-enyne followed by oxidative cleavage. Structure-based design, synthesis of ligands, and biological evaluations of the resulting inhibitors are reported.

SUBMITTER: Ghosh AK 

PROVIDER: S-EPMC2745598 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Design and synthesis of stereochemically defined novel spirocyclic P2-ligands for HIV-1 protease inhibitors.

Ghosh Arun K AK   Chapsal Bruno D BD   Baldridge Abigail A   Ide Kazuhiko K   Koh Yashiro Y   Mitsuya Hiroaki H  

Organic letters 20081018 22


The synthesis of a series of stereochemically defined spirocyclic compounds and their use as novel P2-ligands for HIV-1 protease inhibitors are described. The bicyclic core of the ligands was synthesized by an efficient nBu 3SnH-promoted radical cyclization of a 1,6-enyne followed by oxidative cleavage. Structure-based design, synthesis of ligands, and biological evaluations of the resulting inhibitors are reported. ...[more]

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