Synthesis, (E)/(Z)-isomerization, and DNA binding, antibacterial, and antifungalactivities of novel oximes andO-substituted oxime ethers

Abstract

A series of novel positional oximes (2a{2d),O-methyl oxime ethers (3a{3d), andO-benzyl oxime ethers(4a{4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates.The synthesized compounds were characterized by1H NMR,13C NMR, FT-IR, mass, and elemental analyses fortheir structures and (E)/(Z) isomerizations. Their DNA binding abilities were investigated in vitro by agarose gelelectrophoresis. The antibacterial and antifungal activities were tested also in vitro against eleven bacterial strainsand three fungal strains. The relationship between the structure and the mentioned biological activities was discussed.Compound2ashowed good antibacterial activity against ve types of bacteria. Compounds2b,2c,2d, and4dwereeffective against several microorganisms. Among these,2ashowed the best DNA binding, antibacterial, and antifungalactivities. Therefore,2acan be a pro-drug as an anticancer, antibacterial, and antifungal agent.