Potential antiinflammatory agents. V. Synthesis of metabolites of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) using microbiological hydroxylation.

doi:10.1248/CPB.24.584

Paper

Potential antiinflammatory agents. V. Synthesis of metabolites of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) using microbiological hydroxylation.

Published Apr 25, 1976 · S. Kishimoto, H. Sugino, K. Tanaka

Chemical & pharmaceutical bulletin

Q3 SJR score

4

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0

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Abstract

Microbiological hydroxylation of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284), a new potent antiinflammatory agent, with Penicillium concavo-rugulosum IFO 6226 gave 6-chloro-5-(trans-4'-hydroxycyclohexyl) indan-1-carboxylic acid (1), one of the main metabolites of TAI-284 in rats, in 71% yield. From this product two other metabolites, the corresponding 4'-oxo and cis-4'-hydroxy derivatives (4 and 2), were derived chemically. Catalytic hydrogenation of the 4'-oxo compound (4) over PtO2 afforded the unexpected trans alcohol (1), but reduction of 4 with trimethylphosphite and iridium tetrachloride in aqueous isopropanol gave the desired cis alcohol (2) in 69% yield.

Study Snapshot

TAI-284 shows potential as a potent antiinflammatory agent by generating its main metabolite, 6-chloro-5-(trans-4'-hydroxycyclohexyl) indan-1-carboxylic acid, through microbiological hydroxylation with Penicillium concavo-rug

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Potential antiinflammatory agents. V. Synthesis of metabolites of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) using microbiological hydroxylation.

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