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Synthesis and StructureActivity Relationships of Antifungal Crassinervic Acid Analogs
Author(s) -
Chakor Jyots.,
Musso Loana,
Sardi Paola,
Dallavalle Sabrina
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100288
Subject(s) - cladosporium cladosporioides , chemistry , antifungal , bioassay , aldol reaction , stereochemistry , piper , hydrolysis , biological activity , structure–activity relationship , molecule , lead compound , organic chemistry , combinatorial chemistry , biochemistry , in vitro , traditional medicine , botany , microbiology and biotechnology , catalysis , medicine , biology , genetics
A series of analogs of the natural antifungal compound crassinervic acid, a constituent of Piper crassinervium , were synthesized to gain insight into the most relevant structural features affecting the activity of the parent molecule. Most compounds were prepared by aldol reaction of methyl 3‐acetyl‐4‐hydroxybenzoate with a series of ketones, followed by reduction, hydrolysis, and oxidation. The antifungal activities of crassinervic acid and its analogs was assessed against Cladosporium cladosporioides by using the method of bioautography. The bioassay results allowed us to depict structureactivity relationships for this class of compounds.