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Structure-activity relationships of HIV-1 PR inhibitors containing AHPBA--II. Modification of pyrrolidine ring at P1' proline.

Abstract：

:Systematic replacement in the 3- or 4-position of the pyrrolidine ring at P1' proline was carried out. Compound 26, which has a Cl atom in the 4(S)-position was the most active among inhibitors substituted with other halogen atoms or other substituents. Furthermore, the replacement of the Z group in compound 26 with five- or six-membered fused aromatic heterocycle carbonyl groups produced more potent inhibitors. 7-Methoxybenzofuran-2-carbonyl derivative (44) was the best of these and showed Ki = 4.5 nM against HIV PR and IC90S 0.58 microM and 0.06 microM in chronic and acute infections, respectively. These results suggest that the combination of the 4(S)-CI atom and fused bicyclic heterocycles may be effective in improving their cellular penetration.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Komai T,Higashida S,Sakurai M,Nitta T,Kasuya A,Miyamaoto S,Yagi R,Ozawa Y,Handa H,Mohri H,Yasuoka A,Oka S,Nishigaki T,Kimura S,Shimada K,Yabe Y

doi

10.1016/0968-0896(96)00130-7

subject

Has Abstract

pub_date

1996-08-01 00:00:00

pages

1365-77

issue

8

eissn

0968-0896

issn

1464-3391

pii

0968089696001307

journal_volume

4

pub_type

杂志文章

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