(20R,22ξ)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(piperidin-1'-propionamide-3'-yl)-20-ol | 623550-76-5

• 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: (20R,22ξ)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(piperidin-1'-propionamide-3'-yl)-20-ol
• CAS: 623550-76-5
• 化学式: C₃₅H₆₃NO₃Si
• 分子量: 573.976
• InChiKey: IZSGUIXILFQTFT-OBLOKZGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20R,22ξ)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(piperidin-1'-propionamide-3'-yl)-20-ol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到(20R,22R)-3β-ol-5α-pregnan-20-(piperidin-1'-propionamide-3'-yl)-20-ol
  参考文献：
  名称：

  Azasterols as Inhibitors of Sterol 24-Methyltransferase in Leishmania Species and Trypanosoma cruzi

  摘要：

  This paper describes the synthesis of some novel azasterols based on (20R,22xi)-5alpha-pregnan-20-(piperidin-2-yl)-3beta,20-diol. These compounds are potential inhibitors of the enzyme sterol 24-methyltransferase (24-SMT), which is a vital enzyme in the biosynthesis of ergosterol and related 24-alkyl sterols. Structure-activity studies were undertaken to understand the important features for activity against the enzyme, with the aim of increasing activity and selectivity. The compounds were evaluated for inhibition of recombinant Leishmania major 24-SMT and the effect of compounds on sterol composition and parasite proliferation. Essentially, compounds which showed good activity against the recombinant enzyme had a significant effect on the sterol composition and growth of parasites. The activity of compounds was found to be related to the basicity and stereochemical location of the nitrogen. Also, presence of an unprotected 3beta-OH seemed to be important for activity. However, some azasterols which were not good inhibitors of 24-SMT also showed antiproliferative activity, suggesting that there may be other modes of actions of these compounds.

  DOI：

  10.1021/jm021114j
• 作为产物：
  描述：

  5α-pregnan-20-one tert-butyldimethylsilyl ether 在 platinum(IV) oxide 正丁基锂 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， -78.0~20.0 ℃ 、344.74 kPa 条件下， 反应 170.67h， 生成 (20R,22ξ)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(piperidin-1'-propionamide-3'-yl)-20-ol
  参考文献：
  名称：

  Azasterols as Inhibitors of Sterol 24-Methyltransferase in Leishmania Species and Trypanosoma cruzi

  摘要：

  This paper describes the synthesis of some novel azasterols based on (20R,22xi)-5alpha-pregnan-20-(piperidin-2-yl)-3beta,20-diol. These compounds are potential inhibitors of the enzyme sterol 24-methyltransferase (24-SMT), which is a vital enzyme in the biosynthesis of ergosterol and related 24-alkyl sterols. Structure-activity studies were undertaken to understand the important features for activity against the enzyme, with the aim of increasing activity and selectivity. The compounds were evaluated for inhibition of recombinant Leishmania major 24-SMT and the effect of compounds on sterol composition and parasite proliferation. Essentially, compounds which showed good activity against the recombinant enzyme had a significant effect on the sterol composition and growth of parasites. The activity of compounds was found to be related to the basicity and stereochemical location of the nitrogen. Also, presence of an unprotected 3beta-OH seemed to be important for activity. However, some azasterols which were not good inhibitors of 24-SMT also showed antiproliferative activity, suggesting that there may be other modes of actions of these compounds.

  DOI：

  10.1021/jm021114j