Studies on Topical Antiinflammatory Agents. II. Synthesis and Vasoconstrictive Activity of 21-Substituted Corticosteroids with Sulfur-Containing Moieties

Morihiro MITSUKUCHI; Tomoyuki IKEMOTO; Minoru TAGUCHI; Shohei HIGUCHI; Satoshi ABE; Hajime YASUI; Katsuo HATAYAMA; Kaoru SOTA

doi:10.1248/cpb.37.1795

Morihiro MITSUKUCHI, Tomoyuki IKEMOTO, Minoru TAGUCHI, Shohei HIGUCHI, Satoshi ABE, Hajime YASUI, Katsuo HATAYAMA, Kaoru SOTA

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Keywords: corticosteroid, antiinflammatory agent, 11β-hydroxy-16α, 17α-isopropylidenedioxy-1, 4-pregnadiene-3, 20-dione, 21-alkylthio-6α, 9α-difluoro-11β-hydroxy-16α, 17α-isopropylidenedioxy-1, 4-pregnadiene-3, 20-dione, 21-substituted thiocorticosteroid, vasoconstrictive activity, structure-activity relationship

JOURNAL FREE ACCESS

1989 Volume 37 Issue 7 Pages 1795-1801

DOI https://doi.org/10.1248/cpb.37.1795

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Abstract

As part of the search for new topical antiinflammatory agents, various 21-substituted corticosteroids having sulfur-containing moieties were prepared and tested for vasoconstrictive activity in humans. A structure-activity relationship study revealed that substitution of the 21-hydroxy group with a lower alkyl-thio group enhanced the activity. The activities of the 21-methylthio (3Ad) and the 21-ethylthio (3Ae) compounds were more potent than that of 9α-fluoro-11β, 21-dihydroxy-16β-methyl-17α-valeroyloxy-1, 4-pregnadiene-3, 20-dione (betamethasone 17-valerate, BV).

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