Schönenberger, Helmut and Steinhoff, Dieter (1970) Cytostatic dl- and meso-1,2-diphenylethylenediamines.
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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.
|Additional information (public):||CAN 73:45094 25 Noncondensed Aromatic Compounds Patent 19700618 800-13-5P; 24932-53-4P; 27958-16-3P; 27958-17-4P; 27958-18-5P; 27958-19-6P; 27958-20-9P; 27958-21-0P; 27958-22-1P; 27958-23-2P; 27958-24-3P; 28033-89-8P; 28047-65-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||ethylenediamines diphenyl cytostatic cytostatic diphenylethylenediamines diphenylethylenediamines cytostatic diaminodiphenylethanes cytostatic amines araliph cytostatic anticancer ethylenediamines|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||22 Nov 2010 13:36|
|Last Modified:||22 Nov 2010 13:36|