Synthesis and Antitumor Activity of 2-[3-(2-Chloroethyl)-3-Nitrosoureido]-1,3-Propanediol (Chlonisol)

The reaction of 2-chloroethylisocyanate and 2-amino-1,3-propanediol in MeCN–MeOH yielded 2-[3-(2-chloroethyl) ureido]-1,3-propanediol, which was nitrosated using sodium nitrite in 50% formic acid to obtain 2-[3-(2-chloroethyl)-3-nitrosoureido]-1,3-propanediol (chlonisol). A single administration of chlonisol at a non-toxic dose of 15 mg/kg increased by 170% the median life expectancy of mice with P-388 leukemia and cured 100% of rats with Walker 256 carcinosarcoma.