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Bis(2-chloroethyl)phosphoramidic dichloride [MP(O)Cl2, M = N(CH2CH2Cl)2] has been used as the starting material for the synthesis of O-aryl phosphorodiamidates having the general structure MP(O)(NHR)OAr: 9, R = H, Ar = 4-NO2C6H4; 10, R = H, Ar = C6F5; 11, R = C6H5, Ar = C6F5; 12, R = 4-MeC6H4, Ar = C6F5; and 13, R = 4-EtOC6H4, Ar = C6F5. The phosphorodiamidic chloride precursor to 13 (14) was also isolated. Kinetics for the base-catalyzed hydrolysis of compounds 9--13 were investigated by UV and NMR methods and are considered in connection with service of these compounds as pro(phosphorodiamidic acid mustards) [MP(O)(NHR)OAr leads to MP(O)(NHR)OH] via an E1cB mechanism involving the intermediacy of a mustard-bearing metaphosphorodiimide [MP(O)=NR]. Anticancer screening tests against L1210 lymphoid leukemia in mice indicated that 9--14 are inactive; similar negative results were obtained with the KB cell culture, except in the case of 14 which was marginally active.
F T Chiu, and
F P Tsui, and
G Zon
May 1982,
Journal of pharmaceutical sciences,
F T Chiu, and
F P Tsui, and
G Zon
April 2015,
European journal of medicinal chemistry,
F T Chiu, and
F P Tsui, and
G Zon
December 1983,
Journal of medicinal chemistry,
F T Chiu, and
F P Tsui, and
G Zon
January 2011,
Bioorganic & medicinal chemistry,
F T Chiu, and
F P Tsui, and
G Zon
October 2021,
Bioorganic chemistry,
F T Chiu, and
F P Tsui, and
G Zon
March 2024,
Chemical biology & drug design,
F T Chiu, and
F P Tsui, and
G Zon
March 2018,
Carbohydrate research,
F T Chiu, and
F P Tsui, and
G Zon
January 2003,
Acta poloniae pharmaceutica,
F T Chiu, and
F P Tsui, and
G Zon
June 1983,
Journal of pharmaceutical sciences,
F T Chiu, and
F P Tsui, and
G Zon
January 2016,
Chemical science,
