Open AccessSynthesis of procaine analogues containing pentafluoroethoxy groups in the aromatic nucleus
Author(s) -
I. I. Gaidarzhy,
L. A. Motnyak,
B. V. Kunshenko
Publication year - 2021
Publication title -
voprosy himii i himičeskoj tehnologii/voprosy himii i himičeskoj tehnologii
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.278
H-Index - 7
eISSN - 2413-7987
pISSN - 0321-4095
DOI - 10.32434/0321-4095-2021-136-3-64-72
Subject(s) - procaine , procainamide , chemistry , benzoic acid , stereochemistry , molecule , organic chemistry , pharmacology , anesthesia , medicine
In order to synthesize procaine analogs containing one or two pentafluoroethoxy groups, a method for the synthesis of benzoic acids containing a pentafluoroethoxy group in the ortho-position of the benzene nucleus has been developed. An effective method for the synthesis of procaine structural analogues containing one or two pentafluoroethoxy groups has been proposed. It has been shown that the replacement of the amino group by the pentafluoroethoxy group in the procaine molecule leads to a significant increase in the local anesthetic activity of the obtained compounds. The most active compound was a structural analogue of procainamide containing two pentafluoroethoxy groups in positions 2 and 4. The formation of fluorine-containing analogues of procaine was confirmed by 1H, 19F and 13C NMR spectroscopy and mass spectrometry.