(20(22)E)-cholesta-5,20(22)-dien-3β-ol

• 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: (20(22)E)-cholesta-5,20(22)-dien-3β-ol
• 英文别名: (E)-3β-Hydroxychlolesta-5,20(22)-dien；5, 20(22)-Cholestadienol；(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(E)-6-methylhept-2-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: BWXPSPNRVJBBAK-WLMKBGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 (20(22)E)-cholesta-5,20(22)-dien-3β-ol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以57%的产率得到2-((3S,10R,13S,17R)-10,13-dimethyl-17-((E)-6-methylhept-2-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)tetrahydro-2H-pyran
  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
• 作为产物：
  描述：

  3β-<(tetrahydro-2H-pyran-2-yl)oxy>-5-pregnen-20-one 在 碘 、 magnesium 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (20(22)E)-cholesta-5,20(22)-dien-3β-ol
  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
• Utility of the Wittig reaction for the construction of side chains of steroids starting from pregnenolone
  作者：Steven R. Schow、Trevor C. McMorris

  DOI：10.1021/jo01336a005

  日期：1979.10
• An improved synthesis of (20R,22R)-cholest-5-ene-3β,20,22-triol, an intermediate in steroid hormone formation and an activator of nuclear orphan receptor LXRα
  作者：Benfang Ruan、William K. Wilson、George J. Schroepfer

  DOI：10.1016/s0039-128x(98)00116-0

  日期：1999.6

  Asymmetric dihydroxylation of (20(22)E)-cholesta-5,20(22)-dien-3 beta-ol acetate (2a), prepared from pregnenolone, gave a 1:1 mixture (67% yield) of (20R,22R)-cholest-5-ene-3 beta,20,22-triol 3-acetate (3a) and its 20S,22S isomer 3b. Highly purified 3a and 3b were obtained by semipreparative silver ion high performance liquid chromatography. Saponification of 3a and 3b gave (20R,22R)-cholest-5-ene-3 beta,20,22-triol (4a) and its 20S,22S isomer 4b. This simple approach provided the natural isomer 4a more efficiently than previously described chemical or enzymatic syntheses. Full H-1 and C-13 nuclear magnetic resonance data were presented for triols 4a and 4b and their synthetic precursors. Side-chain conformations of 2a, its 20(22)Z isomer, 4a, and 4b were studied by molecular mechanics and nuclear Overhauser effect difference spectroscopy. (C) 1999 Elsevier Science Inc. All rights reserved.
• Stereospecific synthesis of the four 20,22-epoxycholesterols and of (Z)-20(22)-dehydrocholesterol
  作者：Chang-Yon Byon、Marcel Gut

  DOI：10.1021/jo00885a014

  日期：1976.11
• 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.