Quantitative Structure–Electrochemistry Relationship of 1‐Phenyl‐5‐benzyl‐sulfanyltetrazoles and Their Electrooxidation as a Metabolic Model

Abstract

Abstract The quantitative structure‐electrochemistry relationships study of nineteen derivatives of 1‐phenyl‐5‐benzylsulfanyltetrazole, that seem to be very promising antimycobacterial drugs, resulted in a good correlation relationship between half‐wave potential and energy of HOMO orbital. The study of electrochemical oxidation of these compounds as a model of their possible metabolic degradation was performed. It was possible to propose a scheme of their electrochemical oxidation: the electrochemical oxidation starts on the methoxy group, where by elimination of one electron the radical cation with very short life‐time is formed. The free electron is translocated to the position 2, followed by closing of new cycle with CH 2  of benzylsulfanyl moiety. In the case of 2‐methoxyphenyl tetrazoles this process is followed by the desintegration of the tetrazole ring.