Synthesis and molecular docking study of 6-chloropyrazine-2-carboxylic acid derivatives

Abstract

One of the most lethal and frequent infectious diseases worldwide is tuberculosis. Multi and extensively tuberculosis drug-resistant constitutes a serious problem and emphasizes the need for novel anti-tubercular agents. Accordingly, various pyrazine-2-carboxamides were synthesized and evaluated as potential anti-tuberculosis agents. The synthesis involved reaction of pyrazinoic acids with thionyl chloride to yield acyl chlorides which on treatment with various anilines gave various pyrazine-2-carboxamides. Based on structure-activity relationships extracted from previously published, this paper reported the synthesis and molecular docking study of 6-chloropyrazine-2-carboxamides. Synthesis involved reaction of 6-chloropyrazinoic acid with 2,4,6-trichlorobenzoyl chloride instead of thionyl chloride which listed under the Chemical Weapons Convention as it may use for the production of chemical weapons. Structure identification of 6-chloropyrazine-2-carboxamides was carried out by 1H NMR, 13C NMR, FTIR, and high-resolution mass spectroscopy. It is predicted that 6-chloro-N-octylpyrazine-2-carboxamide has better bioactivity against Mycobacterium tuberculosis, based on molecular docking study.