Studies on the 4-benzoylpyridine-3-carboxamide entity as a fragment model of the Isoniazid–NAD adduct

Organic & Biomolecular Chemistry Pub Date: 2005-01-13 DOI: 10.1039/B415439H

Abstract

An ortho-metallation–electrophilic substitution sequence was employed as a key step to build the 4-benzoylpyridine framework. It was found that 4-benzoylpyridine-3-carboxamide and an N-pyridyl alkylated derivative both exist in a unique cyclized hemiamidal structure, not in the usually expected keto-amide open form. These structures represent fragment models of the Isoniazid–NAD adducts involved in the mechanism of action of the antituberculous drug Isoniazid.

Graphical abstract: Studies on the 4-benzoylpyridine-3-carboxamide entity as a fragment model of the Isoniazid–NAD adduct
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