title: Total synthesis of racemic and (R) and (S)-4-methoxyalkanoic acids and their antifungal activity.
abstract: The total synthesis of 4-methoxydecanoic acid and 4-methoxyundecanoic acid in racemic and stereoselective [(R) and (S)] forms has been accomplished. For stereoselective synthesis of the compounds (S) and (R)-BINOL complexes have been used to generate the required chiral centres. The antifungal activity of these compounds has been studied against different organisms and the results were found to be impressive. The activity of the compounds in racemic and in stereoselective forms was compared. (R)-4-Methoxydecanoic acid was found to be most potent (MIC: 0.019 mg/mL against Candida albicans MTCC 227, C. albicans MTCC 4748, Aspergillus brasiliensis (niger) MTCC 281 and Issatchenkia orientalis MTCC 3020).
authors.affiliation: Organic Chemistry Division-I, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 607, India. biswanathdas@yahoo.com
authors.forename: Biswanath
authors.initials: B
authors.lastname: Das
authors.forename: Digambar Balaji
authors.initials: DB
authors.lastname: Shinde
authors.forename: Boddu Shashi
authors.initials: BS
authors.lastname: Kanth
authors.forename: Avijeet
authors.initials: A
authors.lastname: Kamle
authors.forename: C Ganesh
authors.initials: CG
authors.lastname: Kumar
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001230:Aspergillus / Q000187:drug effects / Q000254:growth & development; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D005230:Fatty Acids, Nonesterified / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010843:Pichia / Q000187:drug effects / Q000254:growth & development; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D005227:Fatty Acids; D005230:Fatty Acids, Nonesterified; C076272:4-oxatetradecanoic acid