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Studies on Topical Antiinflammatory Agents. III. Synthesis of 17 alpha-acyloxy-9 alpha-fluoro-11 beta-hydroxy-16 beta-methyl-1,4-pregnadiene-3,20-dione 21-thio Derivatives and Related Compounds

Studies on Topical Antiinflammatory Agents. III. Synthesis of 17 alpha-acyloxy-9 alpha-fluoro-11 beta-hydroxy-16 beta-methyl-1,4-pregnadiene-3,20-dione 21-thio Derivatives and Related Compounds

M Mitsukuchi, T Ikemoto, M Taguchi, S Higuchi, S Abe, H Yasui, K Hatayama, K Sota

Chem Pharm Bull (Tokyo). 1989 Dec;37(12):3286-93.

PMID: 2632073

Abstract:

A series of 21-thio derivatives of 9 alpha-fluoro-11 beta,17 alpha-dihydroxy-16 beta-methyl-1,4-pregnadiene-3, 20-dione 17-esters and related compounds were synthesized and evaluated as topical antiinflammatory agents. These compounds were prepared by the reaction of 9 alpha-fluoro-11 beta,17 alpha,21-trihydroxy-16 beta-methyl-1,4-pregnadiene-3, 20-dione (betamethasone, I) 17-ester derivatives and various mercapto compounds. A structure-activity relationship study revealed that the structural combination of a thio group at the 21-position and an ester group at the 17-position contributed to vasoconstrictive activity. Among these compounds, the 21-methylthio 17-propanoate compound (6) was found to have the most potent activity, being more potent than betamethasone 17-valerate (BV).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2240280	Betamethasone Valerate Related Compound A		2240-28-0	Price

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