A new family of potential oncostatics: 2-chloroethylnitrososulfamides (CENS)--I. Synthesis, structure, and pharmacological evaluation (preliminary results).
A new series of alkylating agents, 2-chloroethylnitrososulfamides (CENS), were developed on the model of 2-chloroethylnitrosoureas. Starting from chlorosulfonyl isocyanate, a four-step synthesis (carbamoylation-sulfamoylation, Mitsunobu alkylation, deprotection, and nitrosation) gives the title compounds in a 47-58% overall yield. The selection of the nitrosation site can be directed through an alternative route. The pharmacological evaluation shows a significant oncostatic activity towards both A549 and MCF7 cell lines.
Abdaoui
M
M
Laboratoire de Chimie Biomoléculaire (assoc. CNRS), Université de Montpellier-II, France.
Dewynter
G
G
Aouf
N
N
Favre
G
G
Morère
A
A
Montero
J L
JL
D018906:Antineoplastic Agents, Alkylating / Q000138:chemical synthesis*; D002470:Cell Survival / Q000187:drug effects; D004121:Dimethyl Sulfoxide; D005038:Ethylnitrosourea / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008875:Middle Aged; D015538:Nitrosation; D013451:Sulfonic Acids / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D018906:Antineoplastic Agents, Alkylating; D013451:Sulfonic Acids; C017139:1-(2-chloroethyl)-1-nitrosourea; C005741:sulfamic acid; D005038:Ethylnitrosourea; D004121:Dimethyl Sulfoxide