3β,6-dihydroxycholest-5-en-7-one | 26145-92-6

• 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,6-dihydroxycholest-5-en-7-one
• 英文别名: 3β,6-dihydroxy-cholest-5-en-7-one；3β,6-Dihydroxy-cholest-5-en-7-on；(3S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 26145-92-6
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: RIHYAOASXTYLMO-YILGCMHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,6-dihydroxycholest-5-en-7-one 、 双氧水 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3β-hydroxy-6,7-seco-5α-cholestane-6,7-dioic acid
  参考文献：
  名称：

  206.类固醇与沃尔登反演。第四部分 6-酮基锡烷和6：17-二酮基安酮的衍生物

  摘要：

  DOI：

  10.1039/jr9480001043
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 3β,6-dihydroxycholest-5-en-7-one
  参考文献：
  名称：

  206.类固醇与沃尔登反演。第四部分 6-酮基锡烷和6：17-二酮基安酮的衍生物

  摘要：

  DOI：

  10.1039/jr9480001043

文献信息

• 104. Aminosteroids. Part II. Preparation of 3 : 7-diketocholestene
  作者：Jean Barnett、Brenda E. Ryman、F. Smith

  DOI：10.1039/jr9460000526

  日期：——
• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.
• 206. Steroids and the Walden inversion. Part IV. Derivatives of 6-ketositostane and 6 : 17-diketoandrostane
  作者：C. W. Shoppee

  DOI：10.1039/jr9480001043

  日期：——