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Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966.
- Source :
-
Tetrahedron . Oct2013, Vol. 69 Issue 43, p9130-9138. 9p. - Publication Year :
- 2013
-
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-1H-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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 69
- Issue :
- 43
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 90203663
- Full Text :
- https://doi.org/10.1016/j.tet.2013.08.037