Synthesis and pharmacological activity of 6-[(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl)]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids

6-[(E)-2-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids (4 and 8) have been synthesized and show significant activity in reversing the keratinization process in hamster tracheal organ culture and in inhibiting t...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1983-11, Vol.26 (11), p.1653-1656
Main Authors: Dawson, Marcia I, Chan, Rebecca L. S, Derdzinski, Krzysztof, Hobbs, Peter D, Chao, Wan Ru, Schiff, Leonard J
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Animals
Biological Assay
Chemistry
Cricetinae
Enzyme Induction
Exact sciences and technology
Indicators and Reagents
Keratins - metabolism
Mice
Naphthalenes - chemical synthesis
Naphthalenes - pharmacology
Organ Culture Techniques
Organic chemistry
Ornithine Decarboxylase - genetics
Preparations and properties
Skin - drug effects
Skin - enzymology
Structure-Activity Relationship
Terpenoids
Tetradecanoylphorbol Acetate - toxicity
Trachea - drug effects
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Summary:6-[(E)-2-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids (4 and 8) have been synthesized and show significant activity in reversing the keratinization process in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse skin by 12-O-tetradecanoylphorbol-13-acetate, two assays used to measure retinoid activity. The 2-naphthalenecarboxylic acid 8 was more active than 4.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00365a021