Enzyme-Alterable Alkylating Agents. VII. The Design of Short-Lived Mustards¹

Chemoimmunotherapy of cancer. 1

“…This result can be attributed to the greater alkylating action of 4b and is in agreement with studies on the halflives of homologous series of sulfur mustards containing electron-withdrawing groups. 15 In those cases, the reactivity was increased by interposing additional methylene groups between the alkylating group and the electronwithdrawing function.…”

“…The rates obtained were 15-30 times greater than predicted from the following alkylating agents: CH3CH2CH2SCH2CH2CI, C1CH2-CH2S(CH2)3CONH(CH2)3NHCO(CH2)3SCH2CH2Cl. 15 The reason for the anomalous results may be attributed either to charge-transfer complexes between the sulfur atom and the aromatic nucleus or to the compound's water insolubility. It is apparent that the compounds which have been selected are inappropriate for evaluating this chemoimmunotherapeutic approach.…”

Synthesis of Several N,N′-Haloacyl Analogs of N,N′-Diphenylethylenediamine as Potential Antineoplastic Agents

“…Peck et al (10) studied the activity of several mono-and bifunctional nitrogen mustard analogs of acridine and quinoline amides and reported their effectiveness against Ehrlich ascites tumor. Sass et al (11) reported the synthesis of difunctional bromo-and iodothioamides which show promise in cancer chemotherapy. The inhibition of Ehrlich ascites carcinoma and Sarcoma 180 by N,N-bis-(2-I X haloethy1)aliphatic amides was demonstrated by Gazza (12).…”