3-methyl ether 25-hydroxycholesterol | 1620077-79-3

• 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: 3-methyl ether 25-hydroxycholesterol
• 英文别名: (6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-2-ol
• CAS: 1620077-79-3
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: ICKQMIJINGRWRF-JDTILAPWSA-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：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  25-羟基胆甾醇 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以30%的产率得到3-methyl ether 25-hydroxycholesterol
  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

• Structure–activity relationships of oxysterol-derived pharmacological chaperones for Niemann–Pick type C1 protein
  作者：Kenji Ohgane、Fumika Karaki、Tomomi Noguchi-Yachide、Kosuke Dodo、Yuichi Hashimoto

  DOI：10.1016/j.bmcl.2014.05.064

  日期：2014.8

  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.