Cytostatic dl- and meso-1,2-diphenylethylenediamines

Abstract

The dl and meso isomers of the title compds. (I) with cytostatic activity against mammary cancer in rats were prepd. by several methods. Thus, redn. of 3,4-Cl(MeO)C6H3CH:NBu (II) with HgCl2 and Al foil in EtOH on a water bath (method A) gave 31% dl- and 22.2% meso-I.HCl (R = Bu, R1 = 3-Cl, R2 = 4-MeO, R3 = H). dl-I (R = Bu, R1 = 3-Cl, R2 = 4-MeO, R3 = H) was resolved into the (+)- and (-)-isomers by reaction with o,o-dibenzoyl-L-tartaric acid. dl- and meso-I (R = Bu, R1 = 3-Cl, R2 = MeO, R3 = H) were also prepd. by redn. of II with Mg in Et2O-C6H6 (method B) or from 3,4-Cl(MeO)C6H3CH(NHBu)CN by method A redn. (method C) or by method B redn. (method D). Similarly prepd. were the following I (R-R3, isomers, and methods given): Bu, 6-Cl, 3-MeO, H, dl and meso, A, C, and D; Bu, 5-Cl, 2-MeO, H, dl, meso, (+), and (-), A, C, and D; Et, H, H, Et, -, C and D. Redn. of 4-MeOC6H4CH(NEt2)CN with Na in PhMe gave 52% I (R = Et, R1 = H, R2 = 4-MeO, R3 = Et), which was also prepd. by method D.