88876-99-7Relevant academic research and scientific papers
2-Nitroimidazole Dual-Function Bioreductive Drugs: Studies on the Effects on Regioisomerism and Side-Chain Structural Modifications on Differential Cytotoxicity and Radiosensitization by Aziridinyl and Oxiranyl Derivatives
Naylor, Matthew A.,Threadgill, Michael D.,Webb, Paul,Stratford, Ian J.,Stephens, Miriam A.,et al.
, p. 3573 - 3578 (2007/10/02)
A series of 2-nitroimidazoles bearing side chains terminating in or containing aziridinyl and oxiranyl groups has been prepared, and the compounds were evaluated in vitro as hypoxia-selective bioreductively-activated cytotoxins and selected compounds test
Radiosensitizers of hypoxic mammalian cells. 1-(hydroxyaminoalkyl)-substituted nitroimidazoles
Ahmed,Stratford,Jenkins
, p. 1763 - 1768 (2007/10/02)
A series of novel 1-(hydroxyaminoalkyl)-substituted nitroimidazoles has been synthesized as potential radiosensitizers for hypoxic mammalian cells. These compounds were synthesized via N-(hydroxyalkyl)phthalimide nitroimidazole intermediates which, on reaction with hydrazine hydrate, yielded the corresponding amines. The intermediates were prepared by reacting the epoxide derived from nitroimidazole with phthalimide and/or the epoxide derived from phthalimide with the nitroimidazole. The method was used successfully for the preparation of 2-, 4- and 5-nitroimidazole derivatives. In a modification of this procedure, 1-(2-aminoethyl)-2-nitroimidazole has been prepared by a new route which avoids the use of aziridine. These agents were tested for cytotoxicity and radiosensitizing ability in vitro using Chinese hamster V79 cells. All of the 2-nitroimidazoles tested showed toxicity similar to that previously reported for misonidazole and Ro 03-8799 (1-(2-hydroxy-3-piperidinopropyl)-2-nitroimidazole), two compounds currently undergoing clinical evaluation. In addition, all the novel primary amines were shown to function as hypoxic cell radiosensitizers. The 2-nitroimidazole derivatives were the most efficient compounds to be examined and showed at least as much activity as misonidazole.
