5α,6β-dihydroxycholestan-3β-yl-hemisuccinate | 10157-97-8

• 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,6β-dihydroxycholestan-3β-yl-hemisuccinate
• 英文别名: Succinic acid, mono(5,6beta-dihydroxy-5alpha-cholestan-3beta-yl) ester；4-[[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
• CAS: 10157-97-8
• 化学式: C₃₁H₅₂O₆
• 分子量: 520.75
• InChiKey: KTBIQBOAWCFCKL-WOJMBDDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胆固醇琥珀酸单酯 在 MMPP 、 bismuth(lll) trifluoromethanesulfonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以90%的产率得到5α,6β-dihydroxycholestan-3β-yl-hemisuccinate
  参考文献：
  名称：

  Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis

  摘要：

  The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6 beta-hemiphthalates directly from Delta(5)-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 < 5.6 mu M). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.

  DOI：

  10.1021/jm1007769

文献信息

• Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm1007769

  日期：2010.11.11

  The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6 beta-hemiphthalates directly from Delta(5)-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 < 5.6 mu M). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.