(5α)-pregnane-3,20-dione | 128-23-4

• 物质功能分类: 无机化工 - 无机盐 - 氢化物、氮化物、叠氮化物
• 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: (5α)-pregnane-3,20-dione
• 英文别名: 5α-Pregnan-3,20-dion；Pregnan-dion-3,20；(5S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 128-23-4；566-65-4；3986-74-1；4030-89-1；4030-90-4；4034-68-8；4155-84-4；4220-78-4；6570-76-9；7350-00-7；7755-34-2；14615-02-2；14957-73-4；36027-67-5；51154-64-4；51154-65-5；51154-66-6；51154-67-7；51154-68-8；51898-55-6；98301-13-4；102849-00-3
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: XMRPGKVKISIQBV-VOKXCIFESA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  429.2±38.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

概述

氢化黄体酮是由妇科常用药物黄体酮经过氢化得到。

特征鉴别

1. 17位有甲基酮结构，可与高铁离子络合显色。例如，与亚硝基铁氰化钠反应显蓝紫色。
2. 3位羰基，可与异烟肼反应生成腙而显黄色。

参考文献

[1]http://baike.baidu.com/link?url=FMosnY9Y5-bbwPJ-EjViVsLQExIIwpo5sulvGas8fKkIKyie2unLHfLEtId2KWGwzngbb_rWlA25BAn2NuwW-Y5KSrwl9phWBlZhlkhIbTuV0mZthwHqlZOx2TGvBYgMYNmfeIKrAC1Z0zG3ACsLl

生物活性

5a-Pregnane-3,20-dione（5α-孕烷-3,20-二酮）是一种内源性的孕酮代谢物。它能够使肌动蛋白解聚，并降低actin和vinculin的表达。通过影响粘附和细胞骨架分子，5a-Pregnane-3,20-dione参与促进乳腺瘤形成和转移。

靶点

Target	Value
actin
vinculin

体外研究

在MCF-7乳腺癌细胞中，5a-Pregnane-3,20-dione能够减少细胞与基质的附着、粘附斑块、vinculin的表达，并促进F-actin聚合。

文献信息

• FULVENE AND FULVALENE ANALOGS AND THEIR USE IN TREATING CANCERS
  申请人：Arbiser Jack L.

  公开号：US20080275016A1

  公开（公告）日：2008-11-06

  Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are fulvene and/or fulvalene analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers, as well as numerous inflammatory, degenerative and vascular diseases, including various ocular diseases. Representative fulvene and/or fulvalene analogs include fulvene and fulvalene analogues of various dyes, hormones, sugars, peptides, oligonucleotides, amino acids, nucleotides, nucleosides, and polyols. The compounds are believed to function, at least, by inhibiting Nox or ROS. In some embodiments, the Nox is one that is selectively expressed in cancer cells over normal cells, or one that is expressed in higher amounts in cancer cells over normal cells. Thus, the compounds are novel therapeutic agents for a variety of cancers and other diseases.
• US8841276B2
  申请人：——

  公开号：US8841276B2

  公开（公告）日：2014-09-23
• [EN] FULVENE AND FULVALENE ANALOGS AND THEIR USE IN TREATING CANCERS<br/>[FR] ANALOGUES DE FULVÈNE ET FULVALÈNE ET LEUR UTILISATION DANS LE TRAITEMENT DES CANCERS
  申请人：UNIV EMORY

  公开号：WO2008137740A1

  公开（公告）日：2008-11-13

  [EN] Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are fulvene and/or fulvalene analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers, as well as numerous inflammatory, degenerative and vascular diseases, including various ocular diseases. Representative fulvene and/or fulvalene analogs include fulvene and fulvalene analogues of various dyes, hormones, sugars, peptides, oligonucleotides, amino acids, nucleotides, nucleosides, and polyols. The compounds are believed to function, at least, by inhibiting Nox or ROS. In some embodiments, the Nox is one that is selectively expressed in cancer cells over normal cells, or one that is expressed in higher amounts in cancer cells over normal cells. Thus, the compounds are novel therapeutic agents for a variety of cancers and other diseases.
  [FR] L'invention concerne des composés, des compositions pharmaceutiques contenant ces composés, et des procédés de préparation et d'utilisation de ceux-ci. Ces composés consistent en des analogues de fulvène et/ou fulvalène. Ces composés et ces compositions peuvent être utilisés pour traiter et/ou prévenir une grande variété de cancers, notamment les cancers résistant aux médicaments, ainsi que de nombreuses maladies inflammatoires, dégénératives et vasculaires, de même que diverses maladies oculaires. Les analogues représentatifs de fulvène et/ou fulvalène consistent en des analogues de fulvène et fulvalène de divers colorants, hormones, sucres, peptides, oligonucléotides, acides aminés, nucléotides, nucléosides, et polyols. Ces composés semblent fonctionner, au moins, par inhibition de Nox ou des ROS. Dans certains modes de réalisation, le Nox est celui qui est sélectivement exprimé dans des cellules cancéreuses plutôt que dans les cellules normales, ou celui qui est exprimé en plus grandes quantités dans les cellules cancéreuses que dans les cellules normales. Ainsi, les composés consistent en de nouveaux agents thérapeutiques d'une variété de cancers et d'autres maladies.