Issue 4, 2005
From the journal:

Organic & Biomolecular Chemistry

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

Sylvain Broussy,a   Vania Bernardes-Génisson,a   Heinz Gornitzka,b   Jean Bernadou*a  and  Bernard Meuniera  

* Corresponding authors

a Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, Toulouse cedex 4, France
E-mail: bernadou@lcc-toulouse.fr
Fax: 33 (0)5 61 55 30 03
Tel: 33 (0)5 61 33 31 17

b Laboratoire d'Hétérochimie Fondamentale et Appliquée (UMR 5069), Université Paul Sabatier, 118 route de Narbonne, Toulouse cedex 04, France

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B415439H
Article type
Paper
Submitted
06 Oct 2004
Accepted
03 Dec 2004
First published
13 Jan 2005

Org. Biomol. Chem., 2005,3, 666-669

Permissions

Request permissions

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

S. Broussy, V. Bernardes-Génisson, H. Gornitzka, J. Bernadou and B. Meunier, Org. Biomol. Chem., 2005, 3, 666 DOI: 10.1039/B415439H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements