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

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...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1989/07/25, Vol.37(7), pp.1795-1801
Hauptverfasser:	MITSUKUCHI, Morihiro, IKEMOTO, Tomoyuki, TAGUCHI, Minoru, HIGUCHI, Shohei, ABE, Satoshi, YASUI, Hajime, HATAYAMA, Katsuo, SOTA, Kaoru
Format:	Artikel
Sprache:	eng
Schlagworte:	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 Administration, Topical Adrenal Cortex Hormones - chemical synthesis Adrenal Cortex Hormones - pharmacology Adrenal Cortex Hormones - toxicity Alicyclic compounds, terpenoids, prostaglandins, steroids Animals Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - pharmacology Anti-Inflammatory Agents - toxicity antiinflammatory agent Chemical Phenomena Chemistry corticosteroid Exact sciences and technology In Vitro Techniques Mice Mutagens Organic chemistry Preparations and properties Rats Steroids structure-activity relationship Vasoconstriction - drug effects vasoconstrictive activity
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Beschreibung
Zusammenfassung:	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).
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.37.1795