5α,6β,7β-trihydroxycholestan-3β-yl acetate | 62073-83-0

• 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,7β-trihydroxycholestan-3β-yl acetate
• 英文别名: 3β-Acetoxy-5α-cholestan-5,6β,7β-triol；3β-Acetoxy-5α-cholestane-5,6β,7α-triol；[(3S,5R,6R,7R,8S,9S,10R,13R,14S,17R)-5,6,7-trihydroxy-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] acetate
• CAS: 62073-83-0
• 化学式: C₂₉H₅₀O₅
• 分子量: 478.713
• InChiKey: IDCGUDHIXBJBCC-YDYPJVQHSA-N

物化性质

• 熔点：
  178-179 °C(Solv: ethanol (64-17-5))
• 沸点：
  539.8±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5α,6β,7β-trihydroxycholestan-3β-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 5α-cholestane-3β,5,6β,7β-tetrol
  参考文献：
  名称：

  水性分散液中无金属自氧化胆固醇的新产品。

  摘要：

  DOI：

  10.1248/cpb.24.3109
• 作为产物：
  描述：

  cholest-5-ene-3β,7β-diol diacetate 在 高氯酸 、 lipase AY 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 74.0h， 生成 5α,6β,7β-trihydroxycholestan-3β-yl acetate
  参考文献：
  名称：

  Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR

  摘要：

  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.

  DOI：

  10.1021/jm200803d

文献信息

• Regio- and Stereoselective Addition of HO/OOH to Allylic Alcohols
  作者：Xiao-Tao Wang、Wei-Bo Han、Hui-Jun Chen、Qinghong Zha、Yikang Wu

  DOI：10.1021/acs.joc.0c01280

  日期：2020.8.7

  readily react with ethereal H2O2 in the presence of catalytic amounts of Na2MoO4-gly or MoO2(acac)2, affording the C═C trans hydroxylation–hydroperoxylation products in good yields with high regio- and stereoselectivity. Use of enantiomers of cyclic substrates resulted in corresponding enantiopure diol-tert-hydroperoxides. The possibility of further conversion of the diol-tert-hydroperoxides into triols

  在催化量的Na 2 MoO 4 -gly或MoO 2（acac）2的存在下，一系列烯丙醇易于与醚H 2 O 2反应，从而以高收率提供C═C反羟基化-氢过氧化产物具有高区域选择性和立体选择性。使用环状底物的对映异构体产生相应的对映体纯的二醇-叔氢过氧化物。还举例说明了将二醇-叔氢过氧化物进一步转化为具有包含季中心的分离的叔-过氧基团的三醇或线性结构单元的可能性。
• 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.
• A new product of cholesterol by metal-free autoxidation in aqueous dispersion.
  作者：MEIJI KAWATA、MASAHIKO TOHMA、TAKUJI SAWAYA、MICHIYA KIMURA

  DOI：10.1248/cpb.24.3109

  日期：——