(20R)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(pyridin-2-yl)-20-ol | 623550-34-5

• 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)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(pyridin-2-yl)-20-ol
• 英文别名: (20R)-3β-tert-butyldimethylsilyloxy-20-(pyridin-2-yl)-5α-pregnan-20-ol；(1R)-1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-ylethanol
• CAS: 623550-34-5
• 化学式: C₃₂H₅₃NO₂Si
• 分子量: 511.864
• InChiKey: USWHBYHBYFGYTM-QVFWITEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20R)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(pyridin-2-yl)-20-ol 在 platinum(IV) oxide 盐酸 、 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 、 甲醇 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 108.75h， 生成 (20R,22R)-3β-ol-5α-pregnan-20-(piperidin-1'-propionamide-2'-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：

  16-妊娠双烯醇酮 在 咪唑 、 palladium 10% on activated carbon 、 氢气 、 异丙基溴化镁 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~30.0 ℃ 、379.22 kPa 条件下， 反应 25.0h， 生成 (20R)-3β-tert-butyldimethylsilanyloxy-5α-pregnan-20-(pyridin-2-yl)-20-ol
  参考文献：
  名称：

  噻唑/吡啶侧链甾体C-20叔醇的立体选择性合成和抑菌活性

  摘要：

  利用甾体酮和噻唑/吡啶溴化镁的格氏反应，实现了具有噻唑和吡啶侧链的新型甾体C-20叔醇的立体选择性合成。在体外评估这些分子的抗真菌和抗菌活性。大多数化合物对所有测试菌株均表现出显着的抗真菌和抗菌活性。

  DOI：

  10.1016/j.ejmech.2011.05.032

文献信息

• Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations
  作者：Bapurao B. Shingate、Braja G. Hazra

  DOI：10.1016/j.tet.2017.03.029

  日期：2017.4

  Stereoselective synthesis of steroidal C-20 tertiary alcohols with n-butyl, vinyl, furyl, thienyl, thiazolyl, aryl and pyridyl side chains via Grignard reaction or organolithium reagents have been realized starting from readily available 16-dehydropregnenolone acetate. The ionic hydrogenation of steroidal C-20 tertiary alcohols having furyl, methylfuryl, thienyl, phenyl and 4-methoxyphenyl side chains, resulted

  用甾族C-20叔醇的立体选择性合成Ñ丁基，乙烯基，呋喃基，噻吩基，噻唑基，芳基和吡啶基的侧链通过从容易获得的16-脱氢孕烯醇酮乙酸酯开始已经实现了格氏反应或有机锂试剂。具有呋喃基，甲基呋喃基，噻吩基，苯基和4-甲氧基苯基侧链的甾族C-20叔醇的离子加氢，以优异的产率得到具有C-20天然构型的脱氧产物。然而，在相同反应条件下，烷基，噻唑基和吡啶基并入的甾族C-20叔醇失败。通过用呋喃基，噻吩基和4-甲氧基苯基侧链将甾体C-20，21-烯化合物立体选择性还原，得到具有C-20天然构型的饱和化合物，可以进一步突出离子氢化的范围。
• Azasterols as Inhibitors of Sterol 24-Methyltransferase in <i>Leishmania</i> Species and <i>Trypanosoma c</i><i>ruzi</i>
  作者：Filippo Magaraci、Jimenez、Carlos Rodrigues、Juliany C. F. Rodrigues、Marina Vianna Braga、Vanessa Yardley、Kate de Luca-Fradley、Simon L. Croft、Wanderley de Souza、Luis M. Ruiz-Perez、Julio Urbina、Dolores Gonzalez Pacanowska、Ian H. Gilbert

  DOI：10.1021/jm021114j

  日期：2003.10.1

  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.
• Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain
  作者：Bapurao B. Shingate、Braja G. Hazra、Deepak B. Salunke、Vandana S. Pore、Fazal Shirazi、Mukund V. Deshpande

  DOI：10.1016/j.ejmech.2011.05.032

  日期：2011.9

  Stereoselective synthesis of novel steroidal C-20 tertiary alcohols with thiazole and pyridine side chain using Grignard reaction of steroidal ketones and thiazole/pyridine magnesium bromide have been realized. These molecules were evaluated in vitro for their antifungal and antibacterial activities. Most of the compounds exhibited significant antifungal and antibacterial activity against all the tested

  利用甾体酮和噻唑/吡啶溴化镁的格氏反应，实现了具有噻唑和吡啶侧链的新型甾体C-20叔醇的立体选择性合成。在体外评估这些分子的抗真菌和抗菌活性。大多数化合物对所有测试菌株均表现出显着的抗真菌和抗菌活性。