3β-hydroxy-5-androsten-17-one 3-hemisuccinate | 58066-73-2

• 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: 3β-hydroxy-5-androsten-17-one 3-hemisuccinate
• 英文别名: succinic acid mono-(17-oxo-androst-5-en-3β-yl ester)；Bernsteinsaeure-mono-(17-oxo-androst-5-en-3β-ylester)；dehydroepiandrosterone hemisuccinate；4-[[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
• CAS: 58066-73-2
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: UQHKLJJUIGLUKP-MPQCOTKXSA-N

物化性质

• 熔点：
  232-234 °C
• 沸点：
  548.4±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5-androsten-17-one 3-hemisuccinate 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到3β-hydroxy-5-androsten-17-one 3-hemisuccinate chloride
  参考文献：
  名称：

  Syntheses and antiproliferative activities of novel phosphatidylcholines containing dehydroepiandrosterone moieties

  摘要：

  Dehydroepiandrosterone (DHEA) is a natural hormone with many beneficial properties including an anticancer activity. Unfortunately, DHEA is unstable in the body and exhibits cytotoxicity against healthy cells. In this study, a series of new phosphocholines containing DHEA at sn-1 and/or sn-2 positions were prepared. Succinic acid was used as a linker between the active drug and sn-glycero-3-phosphocholine. All the compounds were evaluated in vitro for their antiproliferative activities against four cell lines: Balb/3T3, HL-60, B16, and LNCaP. The results showed that phosphocholines With DHEA at sn-1 and/or sn-2 positions did not have cytotoxic effects on the normal cell line (Balb/3T3). Mixed-chain phospholipids with DHEA and fatty acid residues showed the highest activity against tumor cell lines. The most active compound, tic, showed a moderate cytotoxic effect against the HL-60 and B16 cell lines. (C) 2017 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.12.015
• 作为产物：
  描述：

  丁二酸酐 、 去氢表雄酮 在 4-二甲氨基吡啶 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以68%的产率得到3β-hydroxy-5-androsten-17-one 3-hemisuccinate
  参考文献：
  名称：

  Novel methods for the preparation of dhea derivatives

  摘要：

  这项发明涉及一种从脱氢表雄酮本身生产DHEA衍生物（如7-氧代脱氢表雄酮和7-羟基脱氢表雄酮）的方法。

  公开号：

  US20070032462A1

文献信息

• Schneider; Mason, Journal of Biological Chemistry, 1948, vol. 172, p. 771,776, 778
  作者：Schneider、Mason

  DOI：——

  日期：——
• Nature of the Androgens in Female Adrenal Tumor Urine¹
  作者：John K. Wolfe、Louis F. Fieser、H. B. Friedgood

  DOI：10.1021/ja01847a065

  日期：1941.2
• Conjugated Neuroactive Steroid Compositions And Methods Of Use
  申请人：Marx Christine

  公开号：US20130245253A1

  公开（公告）日：2013-09-19

  The present disclosure provides modified neuroactive steroids. The modified neuroactive steroids may comprise, consist of, or consist essentially of a therapeutic agent and/or a modifying moiety. The modified neuroactive steroid can have modified characteristics as compared to native neuroactive steroids that do not include a modifying moiety and/or therapeutic agent. The modified neuroactive steroid may be, for example, modified pregnenolone, pregnenolone metabolites, allopregnanolone, and/or allopregnanolone metabolites. The modified neuroactive steroids can be used to treat, prevent and/or ameliorating a phenotypic state of interest in a subject.
• US5336485A
  申请人：——

  公开号：US5336485A

  公开（公告）日：1994-08-09
• US5610180A
  申请人：——

  公开号：US5610180A

  公开（公告）日：1997-03-11