(E)-3,3-ethylendioxy-27-nor-5,22-cholestadienoic acid ethyl ester | 1432518-46-1

• 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: (E)-3,3-ethylendioxy-27-nor-5,22-cholestadienoic acid ethyl ester
• 英文别名: ethyl (E,6R)-6-[(8S,9S,10R,13R,14S,17R)-10,13-dimethylspiro[1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-yl]hept-2-enoate
• CAS: 1432518-46-1
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: PIXHANVVXQDCOK-BWENRIMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-ethylenedioxy-5-cholen-24-ol 在 碳酸氢钠 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-3,3-ethylendioxy-27-nor-5,22-cholestadienoic acid ethyl ester 、 (E)-3,3-ethylendioxy-27-nor-5,22-cholestadienoic acid ethyl ester
  参考文献：
  名称：

  27-Nor-Δ4-dafachronic acid is a synthetic ligand of Caenorhabditis elegans DAF-12 receptor

  摘要：

  27-Nor-Delta(4)-dafachronic acid was prepared in nine steps and 14% overall yield by two sequential 2-carbon homologations from 20 beta-carboxyaldehyde-4-pregnen-3-one. Its activity was evaluated in vivo, where it rescued the Mig phenotype of daf-9(rh50) Caenorhabditis elegans mutants and restored their normal resistance to oxidative stress. 27-Nor-Delta(4)-dafachronic acid was also able to directly bind and activate DAF-12 in a transactivation cell-based luciferase reporter assay, although it was less active than the corresponding 25R-and 255 dafachronic acids. The binding mode of the 27-Nor steroid was studied by molecular dynamics using a homology model of the CeDAF-12 receptor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.071

文献信息

• 27-Nor-Δ4-dafachronic acid is a synthetic ligand of Caenorhabditis elegans DAF-12 receptor
  作者：Gisela A. Samaja、Olga Castro、Lautaro D. Alvarez、María V. Dansey、Daiana S. Escudero、Adriana S. Veleiro、Adalí Pecci、Gerardo Burton

  DOI：10.1016/j.bmcl.2013.03.071

  日期：2013.5

  27-Nor-Delta(4)-dafachronic acid was prepared in nine steps and 14% overall yield by two sequential 2-carbon homologations from 20 beta-carboxyaldehyde-4-pregnen-3-one. Its activity was evaluated in vivo, where it rescued the Mig phenotype of daf-9(rh50) Caenorhabditis elegans mutants and restored their normal resistance to oxidative stress. 27-Nor-Delta(4)-dafachronic acid was also able to directly bind and activate DAF-12 in a transactivation cell-based luciferase reporter assay, although it was less active than the corresponding 25R-and 255 dafachronic acids. The binding mode of the 27-Nor steroid was studied by molecular dynamics using a homology model of the CeDAF-12 receptor. (C) 2013 Elsevier Ltd. All rights reserved.