16-benzylidene-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one | 60536-96-1

• 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: 16-benzylidene-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
• 英文别名: (3S,5S,8R,9S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-16-[1-phenyl-meth-(Z)-ylidene]-hexadecahydro-cyclopenta[a]phenanthren-17-one；(3S,5S,8R,9S,10S,13S,14S)-16-benzylidene-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 60536-96-1
• 化学式: C₂₆H₃₄O₂
• 分子量: 378.555
• InChiKey: XVNNBSPKVRWTLT-RGAJKIOOSA-N

物化性质

• 沸点：
  530.3±50.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16-benzylidene-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 在 potassium hydroxide 作用下， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis of substituted tetradecahydrohydroxydimethyl-2H-cyclopenta[a]phenanthrenone derivatives fused with pyrazoline moiety

  摘要：

  A series of pyrazoloandrostane derivatives was synthesized from arylmethylene 3 beta-hydroxyandrostan-17-one derivatives k]which were treated with hydrazine hydrate in different conditions to give the corresponding pyrazolotetradecahydro-3-hydroxy-10,13-dimethyl-2H-cyclopenta[a]phenanthrenone derivatives k]The structures of the newly synthesized compounds were confirmed by the chemical k]elemental k]and spectroscopic analyses.

  DOI：

  10.1134/s1070363215090236
• 作为产物：
  描述：

  表雄酮 、 苯甲醛 在 氢氧化钾 作用下， 生成 16-benzylidene-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
  参考文献：
  名称：

  类固醇组中的研究。第LXXX部分。制备2-和16-oxo-，3,16-和2,16-dioxo-5α-雄甾烷以及2-oxo-5α-胆甾烷

  摘要：

  从17个酮中分三个阶段即可轻松获得16-Oxo-5α-雄甾烷。，与苯甲醛缩合为16-亚苄基17-酮，氢化铝锂-氯化铝还原为16-亚苄基-雄烷二酮，并进行臭氧分解。此序列不适用于环A中3 → 2的氧代基团的转座。此处，将2-亚芳基-6-酮用硼氢化钠还原并在臭氧分解之前被乙酰化：通过用锌和乙酸还原除去3β-乙酰氧基-2-酮的乙酰氧基。

  DOI：

  10.1039/j39700000244

文献信息

• Novel Steroidal[17,16-d]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships
  作者：Fei Yang、Fang Liu、Yong Min、Liqiao Shi、Manli Liu、Kaimei Wang、Shaoyong Ke、Yan Gong、Ziwen Yang

  DOI：10.3390/molecules28062691

  日期：——

  Two series of novel steroidal[17,16-d]pyrimidines derived from natural epiandrosterone and androsterone were designed and synthesized, and these compounds were screened for their potential anticancer activities. The preliminary bioassay indicated that some of these prepared compounds exhibited significantly good cytotoxic activities against human gastric cancer (SGC-7901), lung cancer (A549), and hepatocellular

  从天然表雄酮和雄酮中设计合成了两个系列的新型甾体[17,16-d]嘧啶，并筛选了这些化合物的潜在抗癌活性。初步生物测定表明，与 5-氟尿嘧啶 (5-FU) 相比，这些制备的化合物中的一些对人胃癌 (SGC-7901)、肺癌 (A549) 和肝细胞肝癌 (HepG2) 细胞系表现出显着良好的细胞毒活性、表雄酮和雄酮。尤其是表雄酮和雄酮各自对显示出显着不同的抑制活性，基于激酶测定和分子对接也总结和讨论了可能的构型-活性关系，表明这些甾体的抑制活性[17,
• Androgenic-anabolic activities of some new synthesized steroidal pyrane, pyridine, and thiopyrimidine derivatives
  作者：Mohamed M. Abdalla、Abd El-Galil E. Amr、Mohamed A. Al-Omar、Azza A. Hussain、Mohamed S. Amer

  DOI：10.1134/s106816201405001x

  日期：2014.9