Synthesis, central nervous system activity and teratogenicity of a homothalidomide
Eger, K.; Jalalian, M.; Verspohl, E.J.; Lüpke, N.P.
Arzneimittel-Forschung 40(10): 1073-1075
1990
ISSN/ISBN: 0004-4172 PMID: 2291742 Document Number: 763
The optical isomers of .alpha.-phthalimidoadipinimide (1) were synthesized by a route based on D(+)- and L(-)-amino-.epsilon.-caprolactam (5) as synthon. The isomers of 1 were obtained in high yields by treating D(+)- and L(-)-amino-.epsilon.-caprolactam (5) with N-carboethoxyphthalimide (4), followed by oxidation with benzeneseleninic anhydride (7). The teratogenic potency of both isomers of 1 was studied by the HET-(Hen's Egg Test); 1 caused distinctly lower teratogenic effects in contrast to thalidomide (2). D(-)-1 and L(+)-1 showed sedative effects with a lower activity than 2. Both are more stable in alkaline solution at the same time with a smaller tendency for racemization.
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