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Synthesis, anti-HIV and anti-oxidant activities of caffeoyl 5,6-anhydroquinic acid derivatives.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2010 Jan 15; Vol. 18 (2), pp. 863-9. Date of Electronic Publication: 2009 Dec 03. - Publication Year :
- 2010
-
Abstract
- 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.<br /> (Copyright 2009 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Anti-HIV Agents chemistry
Antioxidants chemistry
Caffeic Acids chemistry
Cell Line, Tumor
Drug Evaluation, Preclinical
Microbial Sensitivity Tests
Molecular Structure
Quinic Acid chemical synthesis
Quinic Acid chemistry
Quinic Acid pharmacology
Stereoisomerism
Structure-Activity Relationship
Anti-HIV Agents chemical synthesis
Anti-HIV Agents pharmacology
Antioxidants chemical synthesis
Antioxidants pharmacology
Caffeic Acids chemical synthesis
Caffeic Acids pharmacology
HIV-1 drug effects
Quinic Acid analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 18
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 20004585
- Full Text :
- https://doi.org/10.1016/j.bmc.2009.11.043