SrasV1, PubMed, Checkpoint, bibRecord, 001B76

Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents.

Identifieur interne : 001B76 ( PubMed/Checkpoint ); précédent : 001B75; suivant : 001B77

Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents.

Auteurs : Tao Ma [République populaire de Chine] ; Li Liu ; Hai Xue ; Li Li ; Chunyan Han ; Lin Wang ; Zhiwei Chen ; Gang Liu

Source :

Journal of medicinal chemistry [ 0022-2623 ] ; 2008.

RBID : pubmed:18284187

Descripteurs français

English descriptors

KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Cell Line, Chromones (chemical synthesis), Chromones (chemistry), Chromones (pharmacology), Combinatorial Chemistry Techniques, Coumarins (chemical synthesis), Coumarins (chemistry), Coumarins (pharmacology), HIV-1 (drug effects), Humans, Pyranocoumarins (chemical synthesis), Pyranocoumarins (chemistry), Pyranocoumarins (pharmacology), Stereoisomerism, Structure-Activity Relationship.
MESH :
- chemical , chemical synthesis : Anti-HIV Agents, Chromones, Coumarins, Pyranocoumarins.
- chemical , chemistry : Anti-HIV Agents, Chromones, Coumarins, Pyranocoumarins.
- chemical , pharmacology : Anti-HIV Agents, Chromones, Coumarins, Pyranocoumarins.
- drug effects : HIV-1.
- Cell Line, Combinatorial Chemistry Techniques, Humans, Stereoisomerism, Structure-Activity Relationship.

Abstract

(+)-Calanolide A ( 1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A ( 15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC 50 = 0.11 microM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC 50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1.

DOI: 10.1021/jm701405p
PubMed: 18284187

Affiliations:

République populaire de Chine

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pubmed:18284187

Le document en format XML

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<front><div type="abstract" xml:lang="en">(+)-Calanolide A ( 1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A ( 15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC 50 = 0.11 microM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC 50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1.</div>
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Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents.

Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents.

Source :

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Abstract

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