Reactions of 1-(2-Chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea Narom-Oxide with Several Biological Model Compounds

The mechanism of antitumor action of 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea Narom-oxide (I) was chemically studied using several biological model compounds. Compound I reacted with piperidine (a model compound for nucleic acid bases) in acetone to form 1-(2-chloroethyl) piperidine, 1, 2-bispiperidinoethane and 1, 1-pentamethylene-3-(3-pyridylmethyl) urea Narom-oxide (III). Moreover, 1-(2-chloroethyl) piperidine reacted with piperidine in acetone to form 1, 2-bispiperidinoethane. Compound I reacted with Nα-acetyl-L-lysine in weakly alkaline conditions and with N-acetyl-DL-penicillamine in acidic methanol (both are model compounds for enzyme proteins having NH2 and SH groups) to form 1-(5-acetylamino-5-carboxy-1-pentamethylene)-3-(3-pyridylmethyl) urea Narom-oxide and N-acetyl-S-nitroso-DL-penicillamine, respectively. Based on these chemical data, a possible antitumor action mechanism of compound I is discussed.