3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester | 120876-14-4

• 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: 3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester
• 英文别名: 3beta-Tetrahydropyranyloxychol-5-en-24-oic acid 24-tetrahydropyranyl ester；oxan-2-yl (4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 120876-14-4
• 化学式: C₃₄H₅₄O₅
• 分子量: 542.8
• InChiKey: ACEYFLGMRXENJS-MGMHTBCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol
  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：

  3,4-二氢-2H-吡喃 、 3B-羟基-D5-胆烯酸 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3β-(Tetrahydropyranyloxy)chol-5-en-24-oic acid 24-tetrahydropyranyl ester
  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

• 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.

  治疗病毒感染的方法包括给予具有以下结构的化合物的有效量：##STR1##或其药用可接受的盐。该化合物通过抑制病毒靶细胞的生长来治疗病毒感染。作为一个具体例子，该化合物可以用于治疗艾滋病感染。
• Method of inhibiting the sodium/proton exchanger NHE3 and method of
  申请人：Magainin Pharmaceuticals, Inc.

  公开号：US05792635A1

  公开（公告）日：1998-08-11

  Aminosterol compounds are described that are useful as inhibitors of the sodium/proton exchanger (NHE). Methods of using such aminosterols compounds are also disclosed, 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.

  描述了一种作为钠/质子交换体(NHE)抑制剂有用的氨基固醇化合物。还披露了使用这种氨基固醇化合物的方法，包括使用抑制一系列NHE的化合物以及使用仅抑制特定NHE的化合物。还披露了有利的筛选技术和用于评估化合物治疗活性的测定方法。
• 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。