Experimental NMR and MS study of benzoylguanidines. Investigation ofE/Zisomerism

Abstract

Molecules containing the guanidinic nuclei possess several pharmacological applications, and knowing the preferred isomers of a potential drug is important to understand the way it operates pharmacologically. Benzoylguanidines were synthesized in satisfactory to good yields and characterized by NMR, Electrospray Ionization Mass Spectrometry (ESI-MS) and Fourrier Transform InfraRed Spectroscopy techniques (FTIR). E/Z isomerism of the guanidines was studied and confirmed by NMR analysis in solution ( Compounds with p-Cl and p-Br aniline moiety exist mainly as Z isomer with a small proportion of E isomer, whereas compounds with p-NO2 moiety showed a decrease in proportion of isomer Z. The results are important for the application of these molecules as enzymatic inhibitors.

Study of the Conformation of Bromated Guanidines with Potential Anti-leishmania Activity

“…These benzoylguanidines had their E/Z isomerism studied by NMR, proving a predominance of the Z isomer. It was possible to observe a isomers ratio, which LQOF-G2 presented 84.7% Z and 15.3% E [25].…”