Synthesis, oxidation potential and anti-mycobacterial activity of isoniazid and analogues: insights into the molecular isoniazid activation mechanism was written by Laborde, Julie;Deraeve, Celine;Lecoq, Lea;Sournia-Saquet, Alix;Stigliani, Jean-Luc;Orena, Beatrice S.;Mori, Giorgia;Pratviel, Genevieve;Bernardes-Genisson, Vania. And the article was included in ChemistrySelect in 2016.Category: pyrazines This article mentions the following:
In this work, a series of 21 INH analogs e.g., pyridine-2-carbohydrazide was synthesized, their oxidation potentials were determined and their anti-mycobacterial activities were evaluated against MTB wild-type and resistant strains. On the contrary to what was postulated, no correlation exists between the easier oxidation of a mol. and its anti-MTB activity toward resistant strains. Based on exptl. data and theor. calculations, an activation mechanism for INH and analogs has been proposed, based on a one-electron oxidation step. It first involves the oxidation of hydrazyl function at the proximal nitrogen followed by a radical transposition to the distal nitrogen, which then induces a β-homolytic cleavage of the C(=O)-N bond to afford diazene and the isonicotinoyl radical species. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Category: pyrazines).
Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Category: pyrazines