“抗孕-53”构型的测定J. 药学学报, 1979, 14(8): 502-505.
引用本文: “抗孕-53”构型的测定J. 药学学报, 1979, 14(8): 502-505.
THE DETERMINATION OF THE CONFIGURATION OF ANORDRIN (2α, 17α-DIETHYNYL-A-NOR-5α-ANDROSTANE 2β, 17β-DIOL DIPROPRIONATE)J. Acta Pharmaceutica Sinica, 1979, 14(8): 502-505.
Citation: THE DETERMINATION OF THE CONFIGURATION OF ANORDRIN (2α, 17α-DIETHYNYL-A-NOR-5α-ANDROSTANE 2β, 17β-DIOL DIPROPRIONATE)J. Acta Pharmaceutica Sinica, 1979, 14(8): 502-505.

“抗孕-53”构型的测定

THE DETERMINATION OF THE CONFIGURATION OF ANORDRIN (2α, 17α-DIETHYNYL-A-NOR-5α-ANDROSTANE 2β, 17β-DIOL DIPROPRIONATE)

  • 摘要: “抗孕-53”是一种新型甾体口服避孕药,存在二差向异构体,对它们一些相关化合物进行了核磁共振测定,根据C2不同构型炔基磁各向异性对19-CH3产生不同的屏蔽效应,导致了19-CH3的特殊位移。比较炔基氢化前后19-CH3化学位移变化情况,同时研究了不同构型的C2-OH对19-CH3的不同吡啶溶剂效应,分别推断二个异构体的构型,确证“抗孕-53”的炔基为α-取向。

     

    Abstract: Anordrin is a new oral steroidal contraceptive. During its systhesis a pair of epimers with different configuration of C2 ethynyl groups is formed simutaneusly.The NMR of Anordrin and its related compounds was studied. The relative position in space between the C2 ethynyl and the 19-CH3 groups of the two epimers are different, thus the shielding effects of the ethynyl group on 19-CH3 are not the same. The chemical shifts of 19-CH3 of the two epimers and their hydrogenated compounds. are compared.The hydroxyl group of steroid formed a spcifically orientated complex with the solvent pyridine, hence the C2 hydroxyl group of the parent compounds of the two epimers have different solvent shifts The chemical shifts of 19-CH3 of their parent compounds in chloroform and pyridine were determined and compared.By means of the two methods mentioned above it is shown that the C2 ethynyl of Anordrin is in α-configuration.Pharmacologic test showed that the β-form epimer has no antifertility effect.

     

/

返回文章
返回