| 364059-48-3

• 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
• CAS: 364059-48-3
• 化学式: C₄₇H₈₈O₃Si₃
• 分子量: 785.47
• InChiKey: JMNLHNNQWZSAFS-WQZUPNDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.33
• 重原子数：
  53.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以62%的产率得到(20S)-1α,25-dihydroxy-26,27-dimethylene-2-methylene-19-norvitamin D₃
  参考文献：
  名称：

  New highly calcemic 1α,25-dihydroxy-19-norvitamin D3 compounds with modified side chain: 26,27-dihomo- and 26,27-dimethylene analogs in 20S-series

  摘要：

  New highly potent 2-substituted (20S)-1alpha,25-dihydroxy-19-norvitamin D-3 analogs with elongated side chain were prepared by Wittig-Horner coupling of A-ring phosphine oxide with the corresponding protected (20S)-25-hydroxy Grundmann's ketones. Biologic evaluation in vitro and in vivo of the synthesized compounds was accomplished. All the synthesized vitamins possessing a 25-hydroxylated saturated side chain were slightly less active (3-5X) than 1alpha,25-dihydroxyvitamin D-3 in binding to the porcine intestinal vitamin D receptor and significantly more potent (12-150X) in causing differentiation of HL-60 cells. In vivo, 2-methylene-26,27-dihomo and 2alpha-methyl-26,27-dimethylene analogs were at least 10 times more active, and 2alpha-methyl-26,27-dihomo compound at least 5 times more active than the vitamin D hormone both in stimulating intestinal calcium transport and bone calcium mobilization (serum calcium increase). It was also established that a 260 pmol dose of the corresponding 2beta-methyl analogs had a similar effect on intestinal calcium transport and a much more pronounced effect on bone calcium mobilization as the same dose of 1alpha,25-dihydroxyvitamin D-3. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00156-8
• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  New highly calcemic 1α,25-dihydroxy-19-norvitamin D3 compounds with modified side chain: 26,27-dihomo- and 26,27-dimethylene analogs in 20S-series

  摘要：

  New highly potent 2-substituted (20S)-1alpha,25-dihydroxy-19-norvitamin D-3 analogs with elongated side chain were prepared by Wittig-Horner coupling of A-ring phosphine oxide with the corresponding protected (20S)-25-hydroxy Grundmann's ketones. Biologic evaluation in vitro and in vivo of the synthesized compounds was accomplished. All the synthesized vitamins possessing a 25-hydroxylated saturated side chain were slightly less active (3-5X) than 1alpha,25-dihydroxyvitamin D-3 in binding to the porcine intestinal vitamin D receptor and significantly more potent (12-150X) in causing differentiation of HL-60 cells. In vivo, 2-methylene-26,27-dihomo and 2alpha-methyl-26,27-dimethylene analogs were at least 10 times more active, and 2alpha-methyl-26,27-dihomo compound at least 5 times more active than the vitamin D hormone both in stimulating intestinal calcium transport and bone calcium mobilization (serum calcium increase). It was also established that a 260 pmol dose of the corresponding 2beta-methyl analogs had a similar effect on intestinal calcium transport and a much more pronounced effect on bone calcium mobilization as the same dose of 1alpha,25-dihydroxyvitamin D-3. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00156-8