Schönenberger, Helmut and Schmidt, F. and Bindl, L. (1975) Cytostatics. 22. Tumor inhibitory N-[bis(2-chloroethyl)aminomethyl]urethanes. Zeitschrift für Krebsforschung und klinische Onkologie 84 (3), pp. 227-240.
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Six title compds. inhibited Yoshida ascites sarcoma in rats. The most active compds., N-[bis(2-chloroethyl)aminomethyl]benzylurethane [58050-46-7] and N-[bis(2-chloroethyl)aminomethyl]phenylurethane [58050-47-8], were curative when given at 60% of the LD50 i.m. distributed over 10 days. The LD50 values of the compds. in rats were 11-55 mg/kg i.m. N,N'-di[bis(2-chloroethyl)aminomethyl]urea [58050-48-9] was considerably less effective owing to its greater instability under physiol. conditions. Similar results were observed after injecting the compds. i.p. into mice bearing sarcoma 180. The antitumor activity of the compds. was evidently due to direct aminoethylation of nucleophilic substrates, as with arom. N mustards, rather than indirect aminoethylation or amidomethylation. The compds. were prepd. by neutralization of bis(2-chloroethyl)amine-HCl [821-48-7], condensation with formaldehyde [50-00-0], and reaction with the appropriate amide.
|Additional information (public):||CAN 84:69431 1-5 Pharmacodynamics 1195149-62-2P; 1195267-67-4P Role: SPN (Synthetic preparation), PRP (Properties), PREP (Preparation) (Cytostatics. 22. Tumor inhibitory N-[bis(2-chloroethyl)aminomethyl]urethanes); 51-79-6; 55-86-7; 5027-16-7; 6781-05-1; 7750-75-6; 7751-31-7; 7751-32-8; 10070-94-7; 58050-49-0 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (neoplasm inhibition by, bis(chloroethyl)aminomethylurethanes in relation to); 58050-42-3P; 58050-43-4P; 58050-44-5P; 58050-45-6P; 58050-46-7P; 58050-47-8P; 58050-48-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and neoplasm inhibitory activity of); 543-28-2; 598-55-0; 621-84-1; 622-46-8; 1746-77-6 Role: BIOL (Biological study) (reaction with bis(chloroethyl)aminomethanol); 821-48-7 Role: BIOL (Biological study) (reaction with formaldehyde); 50-00-0 Role: RCT (Reactant), RACT (Reactant or reagent) (with bis(chloroethyl)amine)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Neoplasm inhibitors (bis(chloroethyl)aminomethylurethanes) chloroethylaminomethylurethane neoplasm inhibitor urethane chloroethylaminomethyl neoplasm inhibitor sarcoma inhibitor chloroethylaminomethylurethane cytostatic chloroethylaminomethylurethane|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 08:34|
|Last Modified:||19 Nov 2010 08:34|