2β,3β-epoxy-1α,25-dihydroxy-3-deoxy-19-nor-previtamin D3 | 1101867-31-5

• 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: 2β,3β-epoxy-1α,25-dihydroxy-3-deoxy-19-nor-previtamin D3
• 英文别名: (1S,2R,6R)-4-[(Z)-2-[(1R,3aR,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-7-oxabicyclo[4.1.0]hept-3-en-2-ol
• CAS: 1101867-31-5
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: BGWBZDCPEOFDGR-HGODFWPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2β,3β-epoxy-1α,25-dihydroxy-6,7-dehydro-3-deoxy-19-nor-previtamin D3 在 喹啉 、 Lindlar's catalyst 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以85%的产率得到2β,3β-epoxy-1α,25-dihydroxy-3-deoxy-19-nor-previtamin D3
  参考文献：
  名称：

  Synthesis and biological activity of previtamin D3 analogues with A-ring modifications

  摘要：

  Synthesis of two novel 6-s-cis analogues of 1 alpha,25-dihydroxyvitamin D-3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2b-(3'-hydroxypropoxy) moiety or a 2 beta,3 beta-epoxy group into 1 alpha,25-(OH)2-19-nor-pre-D-3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.053

文献信息

• Synthesis and biological activity of previtamin D3 analogues with A-ring modifications
  作者：Laura Sánchez-Abella、Susana Fernández、Annemieke Verstuyf、Lieve Verlinden、Vicente Gotor、Miguel Ferrero

  DOI：10.1016/j.bmc.2008.10.053

  日期：2008.12.15

  Synthesis of two novel 6-s-cis analogues of 1 alpha,25-dihydroxyvitamin D-3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2b-(3'-hydroxypropoxy) moiety or a 2 beta,3 beta-epoxy group into 1 alpha,25-(OH)2-19-nor-pre-D-3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation. (C) 2008 Elsevier Ltd. All rights reserved.