Total synthesis of racemic and (R) and (S)-4-methoxyalkanoic acids and their antifungal activity |
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Authors: | Das Biswanath Shinde Digambar Balaji Kanth Boddu Shashi Kamle Avijeet Kumar C Ganesh |
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Affiliation: | a Organic Chemistry Division-I, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 607, India b Chemical Biology Laboratory, Indian Institute of Chemical Technology, Hyderabad 500 607, India |
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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). |
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Keywords: | 4-Methoxyalkanoic acid Racemic and stereoselective [(R) and (S)] forms Total synthesis BINOL complex Antifungal activity |
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