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Title: Dual-function radiosensitizers. Alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol and related compounds: Preparation via an aziridine equivalent

Abstract

An improved synthesis of the dual-function radiosensitizer alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol (2, RB 6145) has been developed. Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development. The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47% yield.

Authors:
; ;  [1]
  1. Warner-Lambert Company, Ann Arbor, MI (USA)
Publication Date:
OSTI Identifier:
5924708
Resource Type:
Journal Article
Journal Name:
Journal of Medicinal Chemistry; (USA)
Additional Journal Information:
Journal Volume: 34:3; Journal ID: ISSN 0022-2623
Country of Publication:
United States
Language:
English
Subject:
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.; 62 RADIOLOGY AND NUCLEAR MEDICINE; RADIOSENSITIZERS; CHEMICAL PREPARATION; ESTERIFICATION; MOLECULAR STRUCTURE; RADIOSENSITIVITY EFFECTS; CHEMICAL REACTIONS; DRUGS; SYNTHESIS; 560151* - Radiation Effects on Animals- Man; 550603 - Medicine- External Radiation in Therapy- (1980-)

Citation Formats

Suto, M J, Stier, M A, and Werbel, L M. Dual-function radiosensitizers. Alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol and related compounds: Preparation via an aziridine equivalent. United States: N. p., 1991. Web. doi:10.1021/jm00107a047.
Suto, M J, Stier, M A, & Werbel, L M. Dual-function radiosensitizers. Alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol and related compounds: Preparation via an aziridine equivalent. United States. doi:10.1021/jm00107a047.
Suto, M J, Stier, M A, and Werbel, L M. Fri . "Dual-function radiosensitizers. Alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol and related compounds: Preparation via an aziridine equivalent". United States. doi:10.1021/jm00107a047.
@article{osti_5924708,
title = {Dual-function radiosensitizers. Alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol and related compounds: Preparation via an aziridine equivalent},
author = {Suto, M J and Stier, M A and Werbel, L M},
abstractNote = {An improved synthesis of the dual-function radiosensitizer alpha-(((2-bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol (2, RB 6145) has been developed. Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development. The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47% yield.},
doi = {10.1021/jm00107a047},
journal = {Journal of Medicinal Chemistry; (USA)},
issn = {0022-2623},
number = ,
volume = 34:3,
place = {United States},
year = {1991},
month = {3}
}