Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids
| Autor: | Isao Minamida, Shunsaku Noguchi, Mikihiko Obayashi, Shoji Kishimoto |
|---|---|
| Rok vydání: | 1974 |
| Předmět: |
chemistry.chemical_classification
5-cyclohexylindan-1-carboxylic acid Chemistry Stereochemistry Chlorine atom Anti-Inflammatory Agents Carboxylic Acids Absolute configuration Stereoisomerism General Chemistry General Medicine humanities Rats Lethal Dose 50 Structure-Activity Relationship Indenes Cyclohexanes Drug Discovery Animals Edema Moiety Optical rotatory dispersion Isopropyl Alkyl |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 22:529-536 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.22.529 |
| Popis: | 6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at C-5 by other alkyl groups such as isobutyl or isopropyl, or the removal of the chlorine atom at C-6 resulted in a considerable reduction of the activities. The resolution of TAI-284 was effected with quinine, and it was found that the antiinflammatory activity virtually resided in the dextro isomer, the absolute configuration of which was assigned the sinister series by the optical rotatory dispersion spectrum and X-ray crystarography. |
| Databáze: | OpenAIRE |
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