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Stereoselective Synthesis of 7α‐ and 7β‐Aminocholesterol as Δ8‐Δ7 Sterol Isomerase Inhibitors, with Fungicidal Activities towards Resistant Strains
Author(s) -
El kihel Laïla,
Choucair Bassima,
Dherbomez Michel,
Letourneux Yves
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<4075::aid-ejoc4075>3.0.co;2-7
Subject(s) - chemistry , sterol , stereochemistry , yeast , saccharomyces cerevisiae , morpholine , bioassay , in vitro , reductase , enzyme , ergosterol , stereoselectivity , biochemistry , isomerase , organic chemistry , biology , cholesterol , catalysis , genetics
A mixture of epimeric 7α‐ and 7β‐aminocholesterol was shown to be a stronger inhibitor of yeast cell growth than morpholine inhibitors. In fact, this epimeric mixture inhibits Δ8‐Δ7‐sterol reductase. This epimeric mixture is fungicidal and active against Saccharomyces cerevisiae resistant strains. Therefore, 7α‐ and 7β‐aminocholesterol were selectively synthesized. According to in vitro bioassay studies on resistant strains such as Candida tropicalis [Amphotericin B resistant; minimum inhibitory concentration (MIC) of Amp B: 12.5 μg/mL], the MIC values for 7β‐aminocholesterol and 7α‐aminocholesterol were found to be 0.8 μg/mL and 1.5 μg/mL, respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)