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Antimicrobial Activity of Basic Cholane Derivatives, VIII
Author(s) -
Bellini A. M.,
Quaglio M. P.,
Mencini E.,
Guarneri M.,
Cavazzini G.,
Fini A.
Publication year - 1989
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19893221208
Subject(s) - antimicrobial , combinatorial chemistry , chemistry , biochemical engineering , organic chemistry , engineering
Two series of new compounds derived from deoxycholic acid have been synthesized: 3,12‐dioxo‐5β‐cholan‐24‐N‐substituted amides and their 3β‐amino and 3β‐N‐alkylamino derivatives. The first series of five compounds 1–5 carries at C‐24 the residue of benzylamine, morpholine, diethanolamine, N,N‐diethyl‐ethylenediamine, and N‐methylpiperazine. The second series of twenty compounds 1A‐D ‐ 5A‐D was prepared by means of reductive amination starting from the compounds of the first series. This reaction proved to be regioselective and stereospecific: it attacks only C‐3 of the steroid moiety and introduces the following axial β‐oriented sustituents: amino, methylamino, ethylamino, and benzylamino. The compounds of the first series showed moderate scattered antimicrobial activity; while introduction of the 3β‐amino and 3β‐N‐alkylamino residue greatly increased activity towards Gram (+) strains; even yeast and fungi appear to be sensitive towards this last series of compounds. The results have been discussed with respect to the nature of the substituents both at C‐3 and C‐24, the highest activity being associated to the hydrophobicity of these residues.