Asymmetric synthesis of α-alkylated carbonyl compounds and their biological application

Document Type : Research and Reference

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1 Chemistry department-Faculty of Science-Tanta University-Tanta Egypt

2 Chemistry department, Faculty of Science, Tanta university, Egypt

3 chemistry department, faculty of science, tanta university

Abstract

Creation of asymmetric centers is the fundamental basis of asymmetric synthesis as the resulting diastereomers or enantiomers are formed in unequal ratio. This is obtained by the creation of novel asymmetric centers either in a chiral molecule or in molecules already containing asymmetric centers, which lead to formation of new diastereomers in unequal ratio. Biological activity is associated with the interactions of a specific stereoisomer with a biological receptor. The vast majority of commercially produced drugs that include one or more stereocenters, but only one of the stereoisomers may biologically active whilst the other may be ineffective. This study included a novel idea for the synthesis of asymmetric reagents by employing quinazolinone derivative. This quinazolinone was interact with ketone’s derivatives, creating quinazolinone Schiff bases which upon deprotonation, subsequently alkylation with alkyl halide led to production of α-alkylated quinazolinone Schiff bases. This Schiff base was then hydrolyzed to give α-alkylated carbonyl compounds that converted to diastereomeric Schiff bases and separated via HPLC using silica gel column. In addition, the target products were tested in-vitro against different types of bacteria and fungi.

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