Document Detail


Synthesis, anti-HIV and anti-oxidant activities of caffeoyl 5,6-anhydroquinic acid derivatives.
MedLine Citation:
PMID:  20004585     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In our continued research on chlorogenic acid analogues and derivatives with improved bioactivity, we have synthesized some caffeoyl 5,6-anhydroquinic acid derivatives. The 1,7 acetonides of chlorogenic acid (15), and of the mono-caffeoyl 5,6-anhydroquinic acids (7-8) showed appreciable anti-HIV activity. The 3,4-dicaffeoyl 5,6-anhydroquinic acid (12) exhibited an anti-HIV activity twice as that of 3,5-dicaffeoylquinic acid (22). The caffeoyl 5,6-anhydroquinic acid derivatives displayed potent anti-oxidant activities. The mono-caffeoyl 5,6-anhydroquinic acids (10-11) were more than twice stronger than chlorogenic acid (21) on SOD-like activity.
Authors:
Chao-Mei Ma; Takuya Kawahata; Masao Hattori; Toru Otake; Lili Wang; Mohsen Daneshtalab
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-12-03
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  18     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2010-02-03     Completed Date:  2010-04-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  863-9     Citation Subset:  IM    
Copyright Information:
Copyright 2009 Elsevier Ltd. All rights reserved.
Affiliation:
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Anti-HIV Agents / chemical synthesis*,  chemistry,  pharmacology*
Antioxidants / chemical synthesis*,  chemistry,  pharmacology*
Caffeic Acids / chemical synthesis*,  chemistry,  pharmacology*
Cell Line, Tumor
Drug Evaluation, Preclinical
HIV-1 / drug effects*
Microbial Sensitivity Tests
Molecular Structure
Quinic Acid / analogs & derivatives*,  chemical synthesis,  chemistry,  pharmacology
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anti-HIV Agents; 0/Antioxidants; 0/Caffeic Acids; 0/caffeoyl 5,6-anhydroquinic acid; 77-95-2/Quinic Acid

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