| 866918-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• CAS: 866918-17-4
• 化学式: C₄₃H₅₇F₂NO₁₅SSi
• 分子量: 926.072
• InChiKey: DSQVWQRTLRFHBH-LGZCNEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  63.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  242.21
• 氢给体数：
  7.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以64%的产率得到[4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenyl] [(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methanesulfonate
  参考文献：
  名称：

  Carbohydrate Sulfonyl Chlorides for Simple, Convenient Access to Glycoconjugates

  摘要：

  [GRAPHICS]The use of carbohydrate sulfonyl chlorides is introduced as a new, facile glycoconjugation method which could find broad applications. We demonstrate the approach by synthesizing a number of glycosylated cholesterol absorption inhibitors which display high inhibitory efficacies in our recently established in vitro assay. Furthermore, we highlight an advantage of the electron-withdrawing nature of the suffonyl linkage which allowed the synthesis of otherwise unstable azetidine conjugates.

  DOI：

  10.1021/ol0502127
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 11.5h， 以69.5 mg的产率得到
  参考文献：
  名称：

  Carbohydrate Sulfonyl Chlorides for Simple, Convenient Access to Glycoconjugates

  摘要：

  [GRAPHICS]The use of carbohydrate sulfonyl chlorides is introduced as a new, facile glycoconjugation method which could find broad applications. We demonstrate the approach by synthesizing a number of glycosylated cholesterol absorption inhibitors which display high inhibitory efficacies in our recently established in vitro assay. Furthermore, we highlight an advantage of the electron-withdrawing nature of the suffonyl linkage which allowed the synthesis of otherwise unstable azetidine conjugates.

  DOI：

  10.1021/ol0502127

文献信息

• Synthesis and in Vitro Evaluation of Inhibitors of Intestinal Cholesterol Absorption
  作者：Lisbet Kværnø,、Moritz Werder、Helmut Hauser、Erick M. Carreira

  DOI：10.1021/jm050422p

  日期：2005.9.1

  We have utilized our recently developed in vitro assay to address two key questions in the design of small-molecule cholesterol absorption inhibitors using ezetimibe, the only drug yet approved for the inhibition of cholesterol absorption in the small intestine, as a starting point: (1) the role of glycosylation and (2) the importance of the beta-lactam scaffold of ezetimibe for inhibitory activity

  我们已经利用我们最近开发的体外测定法来解决使用依泽替米贝设计小分子胆固醇吸收抑制剂的两个关键问题，依泽替米贝是唯一尚未批准的抑制小肠胆固醇吸收的药物，作为出发点：（1 ）糖基化的作用，以及（2）依泽替米贝的β-内酰胺支架对于抑制活性的重要性。合成了多种依泽替米贝的不可水解酚类糖苷，并使用刷状缘膜囊泡测定法证明是胆固醇吸收的活性抑制剂。类似的氮杂环丁烷提供了体外使用各种抑制剂的途径，这表明依泽替米贝的β-内酰胺仅用作适当地定位所需取代基的环骨架。