The first chemical synthesis of the core structure of the benzoylhydrazine-NAD adduct, a competitive inhibitor of the Mycobacterium tuberculosis enoyl reductase

S Broussy, V Bernardes-Génisson…

Index: Broussy, Sylvain; Bernardes-Genisson, Vania; Gornitzka, Heinz; Bernadou, Jean; Meunier, Bernard Organic and Biomolecular Chemistry, 2005 , vol. 3, # 4 p. 666 - 669

Full Text: HTML

Citation Number: 44

Abstract

An isoniazid-NAD adduct has been recently proposed as the ultimate metabolite responsible for the antituberculous activity of isoniazid (INH). Its structure results from binding of the isonicotinoyl radical at C4 position of the nicotinamide ring of NAD with further possible and debated cyclization to form a cyclic hemiamidal derivative. Replacing the pyridine cycle of INH in INH-NAD adduct by a phenyl cycle (BH-NAD adduct) was shown ...