24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7-one | 166896-77-1

• 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: 24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7-one
• 英文别名: 24-t-Butyldimethylsilyloxy-3β-tetrahydropyranyloxy-5α-cholan-7-one；24-t-Butyldimethylsilyloxy-3betatetrahydropyranyloxy-5alpha-cholan-7-one；(3S,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-[tert-butyl(dimethyl)silyl]oxypentan-2-yl]-10,13-dimethyl-3-(oxan-2-yloxy)-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-one
• CAS: 166896-77-1
• 化学式: C₃₅H₆₂O₄Si
• 分子量: 574.96
• InChiKey: DJZINUYETSYGQW-YZEGKOKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7-one 在 sodium hydride 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.33h， 生成
  参考文献：
  名称：

  Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine

  摘要：

  Squalamine (1) is a novel steroidal polyamine which exhibits broad spectrum anti-infective activity. It inhibits the growth of bacteria, both Gram positive and Gram negative, and fungi. The synthesis of 24 xi-squalamine was accomplished in 17 steps from 3 beta-hydroxy-5-cholenic acid. The stereospecific introduction of the 7 alpha-hydroxyl group was achieved by allylic oxidation followed by hydrogenation of the Delta(5) olefin and reduction of the 7-keto group with K-selectride. The polyamine side chain was introduced via reductive amination of an appropriately functionalized 3-keto steroid with a suitably protected spermidine utilizing sodium cyanoborohydride as the reducing agent. The required 24-sulfate was introduced by selective sulfation of the 7 alpha,24 xi-diol with sulfur trioxide-pyridine complex.

  DOI：

  10.1021/jo00121a033
• 作为产物：
  描述：

  3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 在 platinum(IV) oxide 咪唑 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢气 、 dipyridine chromium trioxide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7-one
  参考文献：
  名称：

  Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine

  摘要：

  Squalamine (1) is a novel steroidal polyamine which exhibits broad spectrum anti-infective activity. It inhibits the growth of bacteria, both Gram positive and Gram negative, and fungi. The synthesis of 24 xi-squalamine was accomplished in 17 steps from 3 beta-hydroxy-5-cholenic acid. The stereospecific introduction of the 7 alpha-hydroxyl group was achieved by allylic oxidation followed by hydrogenation of the Delta(5) olefin and reduction of the 7-keto group with K-selectride. The polyamine side chain was introduced via reductive amination of an appropriately functionalized 3-keto steroid with a suitably protected spermidine utilizing sodium cyanoborohydride as the reducing agent. The required 24-sulfate was introduced by selective sulfation of the 7 alpha,24 xi-diol with sulfur trioxide-pyridine complex.

  DOI：

  10.1021/jo00121a033

文献信息

• Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE), pharmaceutical methods and compositions employing such inhibitors, and processes for evaluating the NHE-inhibitory efficacy of compounds
  申请人：Zasloff Michael

  公开号：US20050261508A1

  公开（公告）日：2005-11-24

  Aminosterol compounds are described that are useful as inhibitors of the sodium/proton exchanger (NHE). Methods of using such aminosterols compounds are also enclosed, including those employing compounds that are inhibitors of a spectrum of NHEs as well as those using compounds that are inhibitors of only one specific NHE. Advantageous screening techniques and assays for evaluating a compound's therapeutic activity are also disclosed.

  描述了可用作钠/质子交换器（NHE）抑制剂的氨基固醇化合物。还包括使用这些氨基固醇化合物的方法，包括使用抑制多种NHE的化合物以及使用抑制特定NHE的化合物。还公开了有利的筛选技术和评估化合物治疗活性的测定方法。
• Treatment of neovascularization disorders with squalamine
  申请人：Zasloff Michael

  公开号：US20060166950A1

  公开（公告）日：2006-07-27

  Aminosterol compounds are described that are useful as inhibitors of the sodium/proton exchanger (NHE). Methods of using such aminosterols compounds are also enclosed, including those employing compounds that are inhibitors of a spectrum of NHEs as well as those using compounds that are inhibitors of only one specific NHE. Advantageous screening techniques and assays for evaluating a compound's therapeutic activity are also disclosed.

  本文描述了一种有用的氨基甾醇化合物，可用作钠/质子交换器（NHE）的抑制剂。还包括使用这种氨基甾醇化合物的方法，其中包括使用抑制多种NHE的化合物以及使用仅抑制一种特定NHE的化合物的方法。此外，还公开了有利的筛选技术和评估化合物治疗活性的测定方法。
• Method of inhibiting proliferation of cells by administering an
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05994336A1

  公开（公告）日：1999-11-30

  A method of inhibiting the proliferation of a wide variety of cells is described. This method includes administering an effective amount of a compound having the following structure: ##STR1## or a pharmaceutically acceptable salt thereof. The proliferation of the following types of cells can be inhibited by this method: lymphocytes, fibroblasts, epithelial cells, smooth muscle cells, and human ovarian cancer cells.

  本文描述了一种抑制各种细胞增殖的方法。该方法包括给予以下结构的化合物的有效量：##STR1## 或其药学上可接受的盐。该方法可以抑制以下类型的细胞的增殖：淋巴细胞、成纤维细胞、上皮细胞、平滑肌细胞和人类卵巢癌细胞。
• Method of treating a viral infection by administering a steroid compound
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05763430A1

  公开（公告）日：1998-06-09

  A method of treating a viral infection includes administering an effective amount of a compound having the following structure: ##STR1## or a pharmaceutically acceptable salt thereof. This compound treats the viral infection by suppressing the growth of a viral target cell. As one specific example, this compound may be used to treat HIV infection.

  一种治疗病毒感染的方法，包括给予有效量的化合物，其具有以下结构：##STR1##或其药学上可接受的盐。该化合物通过抑制病毒靶细胞的生长来治疗病毒感染。作为一个具体的例子，该化合物可用于治疗HIV感染。
• Certain aminosterol compounds and pharmaceutical compositions including
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05847172A1

  公开（公告）日：1998-12-08

  Aminosterol compounds are described that are useful as inhibitors of the sodium/proton exchanger (NHE). Methods of using such aminosterols compounds are also enclosed, including those employing compounds that are inhibitors of a spectrum of NHEs as well as those using compounds that are inhibitors of only one specific NHE. Advantageous screening techniques and assays for evaluating a compound's therapeutic activity are also disclosed.

  本文介绍了一种有用的抑制钠/质子交换器（NHE）的氨基固醇化合物。还包括使用这些氨基固醇化合物的方法，包括使用抑制多种NHE的化合物以及使用仅抑制一种特定NHE的化合物。此外，还公开了有利的筛选技术和评估化合物治疗活性的测定方法。