((2R,3S)-3-acetoxy-6-((3S,10R,13S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-3,6-dihydro-2H-pyran-2-yl)methyl acetate | 1296733-98-6

• 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: ((2R,3S)-3-acetoxy-6-((3S,10R,13S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-3,6-dihydro-2H-pyran-2-yl)methyl acetate
• 英文别名: [(2R,3S)-3-acetyloxy-6-[[(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1296733-98-6
• 化学式: C₃₇H₅₈O₇
• 分子量: 614.863
• InChiKey: OYPTYGZOXAJHML-NPQOYZJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  孕烯醇酮 、 1-溴-4-甲基戊烷 在 三氟化硼乙醚 、 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 ((2R,3S)-3-acetoxy-6-((3S,10R,13S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-3,6-dihydro-2H-pyran-2-yl)methyl acetate
  参考文献：
  名称：

  Glucal-conjugated sterols as novel vascular leakage blocker: Structure–activity relationship focusing on the C17-side chain

  摘要：

  A series of glucal-conjugated sterols as novel vascular leakage blocker were identified through design, synthesis and biologically evaluation. In addition, the structure-activity relationship (SAR) of the glucal-conjugated sterols focusing on the C-17-side chain was also established. The sterol analogs linked with the rigid C-17-side chain side chains exhibited potent cell survival activities. In particular, analog 211, which possesses a cyclopentyl oxime moiety, was shown to have excellent pharmacological effects on retinal vascular leakage in a diabetic mouse model. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.027

文献信息

• NOVEL VASCULAR LEAK INHIBITOR
  申请人：Industry-Academic Cooperation Foundation Yonsei University

  公开号：EP2495242B1

  公开（公告）日：2016-05-04
• Glucal-conjugated sterols as novel vascular leakage blocker: Structure–activity relationship focusing on the C17-side chain
  作者：Kyeojin Kim、Sony Maharjan、Changjin Lim、Nam-Jung Kim、Vijayendra Agrawal、Young Taek Han、Sujin Lee、Hongchan An、Hwayoung Yun、Hyun-Jung Choi、Young-Guen Kwon、Young-Ger Suh

  DOI：10.1016/j.ejmech.2014.01.027

  日期：2014.3

  A series of glucal-conjugated sterols as novel vascular leakage blocker were identified through design, synthesis and biologically evaluation. In addition, the structure-activity relationship (SAR) of the glucal-conjugated sterols focusing on the C-17-side chain was also established. The sterol analogs linked with the rigid C-17-side chain side chains exhibited potent cell survival activities. In particular, analog 211, which possesses a cyclopentyl oxime moiety, was shown to have excellent pharmacological effects on retinal vascular leakage in a diabetic mouse model. (C) 2014 Elsevier Masson SAS. All rights reserved.