cholestane-3β,4β,5α-triol | 96290-47-0

• 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: cholestane-3β,4β,5α-triol
• 英文别名: Cholestane-3b,4b,5a-triol；(3S,4S,5S,8S,9S,10R,13R,14S,17R)-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]phenanthrene-3,4,5-triol
• CAS: 96290-47-0
• 化学式: C₂₇H₄₈O₃
• 分子量: 420.676
• InChiKey: UAGLKJAPRSHHAX-ZFALSOKSSA-N

物化性质

• 熔点：
  211-212 °C(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• 沸点：
  501.0±35.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cholestane-3β,4β,5α-triol 在 吡啶 、 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 3β-acetoxy-5-hydroxy-5α-cholestan-4-one
  参考文献：
  名称：

  Julia,S.; Lavaux,J.-P., Bulletin de la Societe Chimique de France, 1963, p. 1238 - 1241

  摘要：

  DOI：
• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 sodium tetrahydroborate 、 高氯酸 、 cerium(III) chloride heptahydrate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 cholestane-3β,4β,5α-triol
  参考文献：
  名称：

  Structure–activity relationships of oxysterol-derived pharmacological chaperones for Niemann–Pick type C1 protein

  摘要：

  Niemann-Pick disease type C is a fatal neurodegenerative disease, and its major cause is mutations in NPC1 gene. This gene encodes NPC1 protein, a late endosomal polytopic membrane protein required for intracellular cholesterol trafficking. One prevalent mutation (11061T) has been shown to cause a folding defect, which results in failure of endosomal localization of the protein, leading to loss-of-function phenotype. We have previously demonstrated that several oxysterols and their derivatives act as pharmacological chaperones; binding of these compounds to NPC1(11061T) mutant protein corrects the localization/maturation defect of the mutant protein. Here, we disclose detailed structure-activity relationships of oxysterol derivatives as pharmacological chaperones for NPC1(11061T) mutant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.064

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。
• Atypical regioselective biohydrolysis on steroidal oxiranes by Aspergillus niger whole cells: Some stereochemical features
  作者：Fabricio R. Bisogno、Alejandro A. Orden、Celeste Aguirre Pranzoni、Diego A. Cifuente、Oscar S. Giordano、Marcela Kurina Sanz

  DOI：10.1016/j.steroids.2007.04.003

  日期：2007.7

  5,6-Epoxycholestan-3 beta-ol derivatives were hydrolyzed in a diastereoconvergent manner by growing and resting cells of several strains of Aspergillus niger, particularly A. niger ATCC 11394. These strains displayed opposite regioselectivity toward each isomer in an a and P epoxide mixture, thus, the nucleophilic attack took place at the less substituted and the most substituted carbon atom on each diasteromer, respectively These biocatalysts opened trisubstituted oxiranes but were unable to hydrolyze the disubstituted oxiranes in the tested sterol derivatives. These findings suggest that A. niger strains possess another hydrolytic ability different from the commercial A. niger epoxide hydrolase (EH) that did not accept this kind of steroidal oxiranes as substrates. (c) 2007 Elsevier Inc. All rights reserved.
• 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.
• 788. Steroidal αβ-epoxy-ketones. Part I. Rearrangement of 4α,5-epoxy-5α-cholestan-3-one and its 4β,5β-isomer by means of the boron trifluoride–ether complex
  作者：D. J. Collins

  DOI：10.1039/jr9590003919

  日期：——
• Isolation and structure elucidation of seven new polyhydroxylated sulfated sterols from the ophiuroid Ophiolepis superba
  作者：M. Valeria D'Auria、Raffaele Riccio、Eugenio Uriarte、Luigi Minale、Junichi Tanaka、Tatsuo Higa

  DOI：10.1021/jo00262a049

  日期：1989.1