3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid | 175026-63-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid
• CAS: 175026-63-8
• 化学式: C₂₂H₃₃NO₄
• 分子量: 375.508
• InChiKey: NEKKKRNUWHXGOX-PLXPDFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  79.12
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid 在 三正丁胺 、 sodium phosphate buffer 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 (S)-2-Amino-3-(4-{3-[(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionyloxy}-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives

  摘要：

  纯的3Z（syn）和3E（anti）睾酮3-[O-(2-羧乙基)]肟的立体异构体被合成，并通过HPLC或TLC分离，然后使用混合酸酐或碳二亚胺-N-羟基琥珀酰亚胺方法制备酪氨酸甲酯（TME）共轭物。后一种方法提供了96%以上保留构型的产物，而混合酸酐方法产生了一个含有26-40%相反立体异构体的混合物。这些立体异构体被用作模型化合物，其他类固醇TME和相应的放射性碘化产物可以根据它们的色谱特性对齐。通过碳二亚胺-N-羟基琥珀酰亚胺法进一步制备了七种4-烯-3-酮类固醇的3-(O-羧甲基)肟TME共轭物。除皮质醇外，立体异构的（Z和E）放射性碘化TME共轭物可以通过TLC分离。此外，从皮质醇及其11α异构体的半琥珀酸盐出发，通过11β-和11α-羟基合成了TME共轭物以及相应的放射性碘标记示踪剂。使用通过将相应类固醇羧基衍生物与牛血清白蛋白作为免疫原制备的兔多克隆抗血清，测试了放射性标记的共轭物作为放射性配体的性质。除去氢化-皮质酮外，立体异构的Z和E放射性碘化TME在结合性质上没有区别。在通过位置11共轭的异构皮质醇示踪剂的情况下，抗血清仅识别立体异构的放射性配体，但是该系统的特异性较差。

  DOI：

  10.1135/cccc19960799
• 作为产物：
  描述：

  3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid
  参考文献：
  名称：

  Preparation and properties of 3-(O-(2-carboxyethyl))oxime derivatives of steroid hormones

  摘要：

  Minerals of 3E and 3Z isomers of 3-(O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17 alpha-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers Mere separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosterone and 17 alpha-methyltestosterone. By the same method, after oximation, methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave (3E,20R)-20-hydroxgpregn-4-en-3-one, 3(O-(2-carboxyethyl))oxime and (3Z,20R)-20-hydroxypregn-4-en-3-one 3-(O-(2-carboxyerhyl))oxime methyl esters. The oxidation and subsequent hydrolysis of these compounds produced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E/Z-isomers of 3-CEO derivatives are designed for the development of immunoanalytical systems, which make use of the bridge heterology based on the geometric isomerism.

  DOI：

  10.1016/0039-128x(95)00198-y

文献信息

• STEROID CONJUGATES, THEIR PREPARATION AND THE USE THEREOF
  申请人：Medexis S.A.

  公开号：EP1523338A1

  公开（公告）日：2005-04-20
• [EN] STEROID CONJUGATES, PREPARATION THEREOF AND THE USE THEREOF<br/>[FR] CONJUGUES STEROIDES, LEUR PREPARATION ET LEUR UTILISATION
  申请人：MEDEXIS S A

  公开号：WO2004006966A1

  公开（公告）日：2004-01-22

  Conjugates comprising one or more steroids conjugated with one or more mammalian proteins are disclosed. The conjugates are useful for diagnosis or treatment of solid cancer and haematological malignancies. Further the conjugates exhibits a synergistic action together with a cytoskeleton acting drug such as Taxol°, which enable the treatment of cancers that otherwise would be non responsive to Taxol°.