Guo‐Liang Lu, Amir Ashoorzadeh, R. Anderson
Oct 28, 2013
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract 5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1 H -imidazole, a preferred precursor, employing an N -bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N -1 and C -2 positions are also described.