Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard.
A four-step synthesis of 5-[N,N-bis(2-chloroethyl)amino]-1-methyl-2-nitroimidazole from 1-methyl-2-nitroimidazole is described. This compound showed similar hypoxia-selective cytotoxicity to the dinitrobenzamide mustard SN 23,862 in UV4 cells (ca. 40-fold), and superior selectivity (> 7-fold) in repair-competent AA8 cells.
Lee
H H
HH
Auckland Cancer Society Research Centre, New Zealand.
Palmer
B D
BD
Wilson
W R
WR
Denny
W A
WA
D000816:Aniline Mustard / Q000031:analogs & derivatives / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D015687:Cell Hypoxia; D002460:Cell Line; D006224:Cricetinae; D003412:Cricetulus; D009593:Nitroimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
C116670:5-(-bis(2-chloroethyl)amino)-1-methyl-2-nitroimidazole; D000970:Antineoplastic Agents; D009593:Nitroimidazoles; C076205:5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide; D000816:Aniline Mustard