3α-benzoyloxy-12-oxo-5β-cholanoic acid-(24)-methyl ester

• 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: 3α-benzoyloxy-12-oxo-5β-cholanoic acid-(24)-methyl ester
• 英文别名: 3α-Benzoyloxy-12-oxo-5β-cholansaeure-(24)-methylester；[(3S,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] benzoate
• 化学式: C₃₂H₄₄O₅
• 分子量: 508.698
• InChiKey: IHSLYRNKWRVRNA-WIDNJEHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α-benzoyloxy-12-oxo-5β-cholanoic acid-(24)-methyl ester 在 sodium hydroxide 、 肼 、 二乙二醇 作用下， 生成 石胆酸
  参考文献：
  名称：

  改良 Wolff--Kishner 法还原类固醇酮和其他羰基化合物

  摘要：

  根据Dutcher 和Wintersteiner2，在通常条件下通过Wow-Kishner 方法还原C3-类固醇酮主要产生相应的Cs-差向异构甲醇和少量预期的Cs-亚甲基产物。在α,P-不饱和酮、胆甾酮的情况下，还原遵循更复杂的过程。除了差向异构不饱和甲醇和少量正常产物A4-胆甾醇外，还分离出饱和甲醇、α-粪甾醇和P-胆甾醇。作者指出，异常还原可以通过以下假设来解释：腙或缩氨基脲部分水解为游离酮，然后被醇钠还原为仲醇。然而，这些可能性被修改后的 WolffKishner red ~ ction 消除，~ , ~ 其中水在加热期间蒸发。此外，该反应中使用过量的水合肼应将再生酮的浓度保持在较低水平。 2 事实上，迄今为止研究的所有 C3-甾体酮都通过改性的 Wolff-Kish20-二酮孕烷得到了正常的 C3-亚甲基化合物(I) 得到在 152-153' 熔化的还原产物，其中两个酮基中的一个未

  DOI：

  10.1021/ja01178a008
• 作为产物：
  描述：

  3α-benzoyloxy-12α-hydroxy-5β-cholane-24-ic acid methyl ester 在 chromium(VI) oxide 、 溶剂黄146 、 氯苯 作用下， 生成 3α-benzoyloxy-12-oxo-5β-cholanoic acid-(24)-methyl ester
  参考文献：
  名称：

  The Preparation and Degradation of Lithocholic Acid

  摘要：

  DOI：

  10.1021/ja01860a036

文献信息

• The Preparation and Degradation of Lithocholic Acid
  作者：Willard M. Hoehn、Harold L. Mason

  DOI：10.1021/ja01860a036

  日期：1940.3
• Effects of Bcl-2 modulation with G3139 antisense oligonucleotide on human breast cancer cells are independent of inherent Bcl-2 protein expression
  作者：Kim N. Chi、Anne E. Wallis、Chow Hwee Lee、Daniel Lopez de Menezes、Jason Sartor、Wieslawa H. Dragowska、Lawrence D. Mayer

  DOI：10.1023/a:1017371013487

  日期：2000.10

  We have investigated the effects of transient Bcl-2 down-regulation induced by the Bcl-2 antisense oligodeoxynucleotide (ODN) G3139 (Genta Incorporated) in high Bcl-2 protein expressing, estrogen receptor (ER) positive MCF-7 and low Bcl-2 expressing, ER negative MDA435/LCC6 human breast cancer cells. Treatment with Bcl-2 antisense ODN in vitro caused > 80% reduction of Bcl-2 protein levels in a sequence specific manner for both cell lines. Maximum mRNA reduction was achieved within 24 h of the first antisense ODN exposure whereas full protein down-regulation required antisense exposure over 48 h. This Bcl-2 reduction was associated with 80-95% loss of viable cells compared to untreated cells. Similar cytotoxic effects were observed in both cell lines despite a nine-fold intrinsic difference in Bcl-2 protein expression suggesting that the relative degree of down-regulation of Bcl-2 is more important than the absolute reduction. Cell death associated with G3139 exposure exhibited properties indicative of apoptosis such as mitochondrial membrane depolarization and caspase activation. Combined treatment with G3139 and cytotoxic agents resulted in additive cytotoxicity in both cell lines. However, under most conditions studied, the direct cytotoxic activity of G3139 antisense was not synergistic with the cytotoxic agents. These results suggest that while Bcl-2 clearly constitutes an attractive therapeutic target due to its role in regulating apoptosis in breast cancer cells, additional mechanisms are important in the control of apoptosis arising from exposure to anticancer agents in vitro.
• Reduction of Steroid Ketones and other Carbonyl Compounds by Modified Wolff--Kishner Method
  作者：[not available]. Huang-Minlon

  DOI：10.1021/ja01178a008

  日期：1949.10

  concentration of the regenerated ketone a t a low level.2 In fact all the C3-steroid ketones so far investigated gave the normal C3-methylenic compounds by the modified Wolff-Kish20-diketopregnane (I) gave a reduced product melting a t 152-153' in which one of the two keto groups is unattacked. In view of the fact that the 20-keto compounds, such as A5-pregnen-3 (P)-ol20-one (IV) and its hydrogenation product

  根据Dutcher 和Wintersteiner2，在通常条件下通过Wow-Kishner 方法还原C3-类固醇酮主要产生相应的Cs-差向异构甲醇和少量预期的Cs-亚甲基产物。在α,P-不饱和酮、胆甾酮的情况下，还原遵循更复杂的过程。除了差向异构不饱和甲醇和少量正常产物A4-胆甾醇外，还分离出饱和甲醇、α-粪甾醇和P-胆甾醇。作者指出，异常还原可以通过以下假设来解释：腙或缩氨基脲部分水解为游离酮，然后被醇钠还原为仲醇。然而，这些可能性被修改后的 WolffKishner red ~ ction 消除，~ , ~ 其中水在加热期间蒸发。此外，该反应中使用过量的水合肼应将再生酮的浓度保持在较低水平。 2 事实上，迄今为止研究的所有 C3-甾体酮都通过改性的 Wolff-Kish20-二酮孕烷得到了正常的 C3-亚甲基化合物(I) 得到在 152-153' 熔化的还原产物，其中两个酮基中的一个未
• McKenzie et al., Journal of Biological Chemistry, 1948, vol. 173, p. 271,279
  作者：McKenzie et al.

  DOI：——

  日期：——