(3S,20S)-3β-acetoxy-5α-pregn-7-en-20-yl-methanoic acid | 114552-77-1

• 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: (3S,20S)-3β-acetoxy-5α-pregn-7-en-20-yl-methanoic acid
• 英文别名: 3β-acetoxy-23,24-dinor-5α-chol-7-en-22-oic acid；3β-Acetoxy-23,24-dinor-5α-chol-7-en-22-saeure；(2S)-2-[(3S,5S,9R,10S,13R,14R,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS: 114552-77-1
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: VWHVCMHAAXPHER-GTSAMIDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,20S)-3β-acetoxy-5α-pregn-7-en-20-yl-methanoic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Lathosterol side chain amides—A new class of human lathosterol oxidase inhibitors

  摘要：

  Inhibition of cholesterol biosynthesis offers the opportunity for treatment of cardiovascular diseases. Numerous enzymes are involved in the post-squalene part of this biosynthesis, and selective inhibitors for almost all of the enzymes involved there have been described in literature. The only exception is the enzyme lathosterol oxidase (EC 1.14.21.6), for which up to now no selective inhibitor has been found. Up to date only triarimol has been reported as a weak inhibitor. In this paper we report on lathosterol side chain amides as a new class of selective lathosterol. oxidase inhibitors. To study the influence of different sterol amides on inhibition of this enzyme, numerous compounds were prepared and the sterol patterns resulting from incubation of HL 60 cells with these enzyme inhibitors were monitored in a whole cell screening assay by means of GUMS analysis. Small alkyl residues at the amide nitrogen (hydrogen and methyl) lead to an inhibition of the enzyme Delta 24-reductase, the N-ethyl and N-propyl derivatives show a dual action, inhibiting both Delta 24-reductase and lathosterol oxidase. Lathosterol- derived amides with larger substituents (butyl, isobutyl, tert-butyl, pentyl) at the amide nitrogen were found to be selective inhibitors of lathosterol oxidase. The corresponding 3 beta-acetoxy derivatives showed comparable activities and can be considered as prodrugs, since they are transformed into the 3 beta-hydroxy derivatives under the test conditions, as proven by HPLC analysis. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.10.015
• 作为产物：
  描述：

  5-dihydroergosteryl acetate 在 吡啶 、 sodium dichromate 、 氯仿 、 硫酸 作用下， 生成 (3S,20S)-3β-acetoxy-5α-pregn-7-en-20-yl-methanoic acid
  参考文献：
  名称：

  DE964775

  摘要：

  公开号：

文献信息

• Lathosterol side chain amides—A new class of human lathosterol oxidase inhibitors
  作者：Martin Giera、Delphine Renard、Florian Plössl、Franz Bracher

  DOI：10.1016/j.steroids.2007.10.015

  日期：2008.3

  Inhibition of cholesterol biosynthesis offers the opportunity for treatment of cardiovascular diseases. Numerous enzymes are involved in the post-squalene part of this biosynthesis, and selective inhibitors for almost all of the enzymes involved there have been described in literature. The only exception is the enzyme lathosterol oxidase (EC 1.14.21.6), for which up to now no selective inhibitor has been found. Up to date only triarimol has been reported as a weak inhibitor. In this paper we report on lathosterol side chain amides as a new class of selective lathosterol. oxidase inhibitors. To study the influence of different sterol amides on inhibition of this enzyme, numerous compounds were prepared and the sterol patterns resulting from incubation of HL 60 cells with these enzyme inhibitors were monitored in a whole cell screening assay by means of GUMS analysis. Small alkyl residues at the amide nitrogen (hydrogen and methyl) lead to an inhibition of the enzyme Delta 24-reductase, the N-ethyl and N-propyl derivatives show a dual action, inhibiting both Delta 24-reductase and lathosterol oxidase. Lathosterol- derived amides with larger substituents (butyl, isobutyl, tert-butyl, pentyl) at the amide nitrogen were found to be selective inhibitors of lathosterol oxidase. The corresponding 3 beta-acetoxy derivatives showed comparable activities and can be considered as prodrugs, since they are transformed into the 3 beta-hydroxy derivatives under the test conditions, as proven by HPLC analysis. (C) 2007 Elsevier Inc. All rights reserved.
• DE964775
  申请人：——

  公开号：——

  公开（公告）日：——