Quantitative Structure-Electrochemistry Relationship of 1-Phenyl-5-benzyl-sulfanyltetrazoles and Their Electrooxidation as a Metabolic Model
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 -CH2- of benzylsulfanyl moiety.
In the case of 2-methoxyphenyl tetrazoles this process is followed by the desintegration of the tetrazole ring.