(20S)-de-A,B-25-hydroxy-22-oxacholestan-8-one | 884488-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (20S)-de-A,B-25-hydroxy-22-oxacholestan-8-one
• 英文别名: (1S,3aR,7aR)-1-((S)-1-(3-hydroxy-3-methylbutoxy)ethyl)-7a-methyloctahydro-4H-inden-4-one；(1S,3aR,7aR)-1-((1S)-1-(3-hydroxy-3-methylbutoxy)ethyl)-7a-methyloctahydro-4H-inden-4-one；(1s,3ar,7ar)-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyloctahydro-4h-inden-4-one；(1S,3aR,7aR)-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 884488-07-7
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: RNNQSWKJXYHFRW-QDEZUTFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20S)-de-A,B-25-hydroxy-22-oxacholestan-8-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以88%的产率得到(1S,3aS,7aR)-1-((1S)-1-(3-hydroxy-3-methylbutoxy)ethyl)-7a-methyloctahydro-4H-inden-4-one
  参考文献：
  名称：

  [EN] VITAMIN-D ANALOGUE USEFUL IN A PHARMACEUTICAL COMPOSITION
  [FR] ANALOGUE DE VITAMINE D CONVENANT DANS UNE COMPOSITION PHARMACEUTIQUE

  摘要：

  本发明涉及14-epi-1α,25-(OH)2D3类似物，其中侧链含有至少两个杂原子，以及药物组合物，以及它们用于治疗或预防骨疾病，如骨质疏松症。

  公开号：

  WO2006042383A1
• 作为产物：
  描述：

  (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 在 palladium on activated charcoal N-甲基吗啉 、 咪唑 、 氢氟酸 、 potassium tert-butylate 、 氢气 、 氧气 、 氢化钾 、 碳酸氢钠 、 二甲基亚砜 、 pyridinium chlorochromate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 异丙醇 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 12.0h， 生成 (20S)-de-A,B-25-hydroxy-22-oxacholestan-8-one
  参考文献：
  名称：

  A new approach to the synthesis of the 25-hydroxy-22-oxa-vitamin D3 side chain

  摘要：

  An efficient new method is described for the construction of the 25-hydroxy-22-oxavitamin D-3 side-chain, which is present in several analogues of calcitriol with antitumour activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01056-3

文献信息

• VITAMIN D RECEPTOR ACTIVATORS AND METHODS OF MAKING
  申请人：Von Geldern Thomas W.

  公开号：US20090131379A1

  公开（公告）日：2009-05-21

  The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

  该发明涉及一种维生素D受体激活剂化合物，包括这种化合物的组合物，使用这种化合物和组合物的方法，制备这种化合物的过程，以及在这些过程中获得的中间体。
• Vitamin D receptor activators and methods of making
  申请人：Von Geldern Thomas W.

  公开号：US08377913B2

  公开（公告）日：2013-02-19

  The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

  本发明涉及一种维生素D受体激活剂化合物，包括该化合物的组合物、使用该化合物和组合物的方法、制备该化合物的方法以及在这些过程中获得的中间体。
• Synthesis and biological activities of new 1α,25-dihydroxy-19-norvitamin D3 analogs with modifications in both the A-ring and the side chain
  作者：Masato Shimizu、Yukiko Miyamoto、Emi Kobayashi、Mika Shimazaki、Keiko Yamamoto、Wolfgang Reischl、Sachiko Yamada

  DOI：10.1016/j.bmc.2006.01.061

  日期：2006.6

  In a series of studies on structure-activity relationships of 2-substituted 19-norvitamin D analogs, we found that 1 alpha,25-dihydroxy-19-norvitamin D-3 analogs with 2 beta-hydroxyethoxy or 2E-hydroxyethylidene moieties show strong binding affinity for the vitamin D receptor (VDR) as well as marked transcriptional activity. To further examine the effects of side chain structure on the activity of 2-substituted 19-norvitamin D analogs, we have synthesized new 19-norvitamin D3 analogs with modifications in both the A-ring at the C(2) position and the side chain. The side chains of these analogs contained a double bond between C(22) and C(23) or an oxygen atom at C(22). The biological activity of the analogs was evaluated in vitro. All the side chain-modified analogs were less active than 1 alpha,25-dihydroxyvitamin D-3 1e and the parent compounds 3-6e possessing a natural 20R-configuration in binding to the VDR, but, except for the (20R)-22-oxa analogs 3-6d, were significantly more potent in transcriptional activity. Of the side-chain-modified analogs 4 and 5, the 2 beta-hydroxyethoxy- and 2E-hydroxyethylidene-22,24-diene-24a,26a,27a-trihorno analogs showed markedly higher transcriptional activity (25- and 17.5-fold, respectively) compared with le. Elongation of the side chain at the C-24, C-26, and C-27 positions and introduction of a 22,24-diene moiety strongly increased transcriptional activity, as seen in the 20-epi analogs 3-6f. (c) 2006 Elsevier Ltd. All rights reserved.
• US8377913B2
  申请人：——

  公开号：US8377913B2

  公开（公告）日：2013-02-19
• US9221753B2
  申请人：——

  公开号：US9221753B2

  公开（公告）日：2015-12-29