(3S,20S)-20-N-pentylcarbamoyl-5α-pregn-7-en-3β-yl acetate | 1058719-67-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,20S)-20-N-pentylcarbamoyl-5α-pregn-7-en-3β-yl acetate
• 英文别名: [(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2S)-1-oxo-1-(pentylamino)propan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1058719-67-7
• 化学式: C₂₉H₄₇NO₃
• 分子量: 457.697
• InChiKey: PONCSVAITCEUAX-ICPRAOGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,20S)-20-N-pentylcarbamoyl-5α-pregn-7-en-3β-yl acetate 在 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 16.0h， 以100%的产率得到(3S,20S)-20-N-pentylcarbamoyl-5α-pregn-7-en-3β-ol
  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：

  、 1-氨基戊烷 以 二氯甲烷 为溶剂， 以61%的产率得到(3S,20S)-20-N-pentylcarbamoyl-5α-pregn-7-en-3β-yl acetate
  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