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- W2072946816 endingPage "2028" @default.
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- W2072946816 abstract "Ausgehend von D- und L-Ornithin werden die Enantiomeren von Supidimid (2) dargestellt. Im Gegensatz zum strukturverwandten Thalidomid (1) zeigt Supidimid keine teratogene Aktivitat, wirkt aber ebenfalls als Sedativum bzw. Tranquilizer. Anhand einer Rontgenstrukturanalyse von (R)-(+)-Supidimid werden die Unterschiede im Molekulbau von Supidimid und Thalidomid verglichen. Die reinen Enantiomeren von Supidimid sind um den Faktor 6 besser loslich als das Racemat. Der Grund hierfur liegt in den Kristallgitterkraften: In den reinen Enantiomeren sind die Molekule uber schwache H-Brucken kettenformig verknupft, wahrend im Racemat Dimere vorliegen, die uber starke, zentrosymmetrische H-Brucken gebildet werden.EPC ≠) Synthesis of (R)-(+)- and (S)-(-)-Supidimide and Crystal Structure Analysis of (R)-(+)-SupidimideStarting from D- and L-ornithine, the enantiomers of supidimide (2) were prepared. In contrast to the structurally related thalidomide (1), supidimide shows no teratogenic activity, but has similar sedative and tranquilizing properties as thalidomide. By means of an X-ray analysis of (R)-(+)-supidimide the differences in the molecular structure of supidimide and thalidomide are discussed. Compared with the racemic mixture, the pure enantiomers of supidimide are better soluble by a factor of 6. The reason for this fact lies in the crystal lattice forces: In the pure enantiomers, the molecules are linked to chains by weak hydrogen bonds, whereas dimeric units occur in the racemic compound, which are built up by strong, centrosymmetrical hydrogen bonds." @default.
- W2072946816 created "2016-06-24" @default.
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- W2072946816 date "1983-11-15" @default.
- W2072946816 modified "2023-09-27" @default.
- W2072946816 title "EPC-Synthese von (R)-(+)- und (S)-(−)-Supidimid und Kristallstrukturanalyse von (R)-(+)-Supidimid" @default.
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- W2072946816 doi "https://doi.org/10.1002/jlac.198319831117" @default.
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