The nature of the toxicity of someN-nitroso-N-(2-chloroethyl)carbamates in animals and man

Synthesis and Evaluation of Several New (2-Chloroethyl)nitrosocarbamates as Potential Anticancer Agents

“…Compound 11 was prepared from 10 (440 mg, 2.18 mmol) by the similar procedure as previously described for the preparation of 3. The product was purified using column chromatography (99:1 CH 2Cl2:MeOH), and a yellow oil was obtained that solidified in the freezer: yield 70 mg (14%); mp 78-80 °C; MS m/z 231 (M + H) + ; 1…”

“…Finally, commercially available 2,3,4,6-tetra-O-benzyl-1-R,β-D-glucopyranose was reacted with 2-chloroethyl isocyanate, deblocked by hydrogenolysis, peracetylated, and nitrosated with NOCl to give 24 (Scheme 4). All samples were characterized by FAB-MS, 1 H NMR, and IR spectroscopy and TLC and CHN analysis prior to evaluation.…”

“…The crude product was chromatographed (CHCl3). The desired fractions were collected, concentrated and dried in vacuo over P2O5: yield 930 mg (73.2%); mp 52-54 °C; MS m/z 460 (M + Li) + ; 1 Carbamic Acid, (2-Chloroethyl)nitroso-2,3,4,6-tetra-Oacetyl-1-r,β-D-glucopyranose Ester (24) Using 23 (912 mg, 2.0 mmol). The same procedure as described for the preparation of 3 was used to prepare 24.…”

“…The observed activity of ethyl (2-chloroethyl)- N -nitrosocarbamate, and the similarity of this class of alkylating agent to the clinically used N -(2-chloroethyl)- N -nitrosourea anticancer drugs, has led us to investigate a number new of N -(2-chloroethyl)- N -nitrosocarbamates for evaluation as potential anticancer alkylating agents. Several such compounds, although only modestly water soluble, have shown significant increases in life span and/or curative benefits in mice implanted with P388 leukemia .…”