Synthesis ofβ-m-[di (2-chloroethyl) amino] benzoyl-propionic acid and an investigation of its antitumoral activity

Synthesis of the antileukemic compound N,N''-[5-[bis(2-chloroethyl)amino]-1,3-phenylene]bisurea

“…2 The objective of the present work was to prepare for biological testing a derivative of aniline mustard in which two ureido functions are located in positions meta to the bis(2-chloroethyl)amino moiety, the potential advantages of this orientation having been discussed previously. [3][4] Recent syntheses of multifunctional aromatic nitrogen mustards have indicated continuing research in this area5-6 Of particular interest were methods described for the synthesis of a mustard from picramic acid,7 in which either ethylene oxide or 2-chloroethanol was used to introduce the bis(2-hydroxyethyl) moiety onto an amino function (in picramic acid) subject to deactivating influences. Numerous attempts to convert 3,5-dinitroaniline into its N,iV-bis(2-hydroxyethyl) derivative (a possible intermediate for the present synthesis) under similar conditions were unsuccessful.…”