Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

Zaman, S.; Campaner, P.; Abell, A.

doi:10.1016/j.bmc.2006.09.009

Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

Date

2006

Authors

Zaman, S.

Campaner, P.

Abell, A.

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Journal article

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Bioorganic and Medicinal Chemistry, 2006; 14(24):8323-8331

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Shazia Zaman, Pietro Campaner and Andrew D. Abell

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10.1016/j.bmc.2006.09.009

Abstract

A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition.

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https://doi.org/10.1016/j.bmc.2006.09.009

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http://hdl.handle.net/2440/34879

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Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

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