2β-(3-hydroxypropoxy)-1α,25-dihydroxy-19-norvitamin D3

• 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-(3-hydroxypropoxy)-1α,25-dihydroxy-19-norvitamin D3
• 化学式: C₂₉H₅₀O₅
• 分子量: 478.713
• InChiKey: SGILNBMDWGBSLS-IKTRVIDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (1R,3aR,7aR)-1-[(1R)-1,5-二甲基-5-[(三乙基硅烷基)氧基]己基]八氢-7a-甲基-4H-茚-4-酮 在 四氢呋喃 、 正丁基锂 、 18-冠醚-6 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.5h， 生成 2β-(3-hydroxypropoxy)-1α,25-dihydroxy-19-norvitamin D3
  参考文献：
  名称：

  Synthesis and Biological Activity of 2-Hydroxy and 2-Alkoxy Analogs of 1.alpha.,25-Dihydroxy-19-norvitamin D3

  摘要：

  1 alpha,2 alpha,25 Trihydroxy-19-norvitamin D-3, 1 alpha,2 beta,25-trihydroxy-19-norvitamin D-3, and their alkoxy analogs were efficiently prepared in a convergent synthesis, starting with (-)-quinic acid and a Windaus-Grundmann type ketone. Configurations of the A-ring fragment substituents were determined by H-1,H-1 COSY 2D spectra and H-1 NOE difference spectroscopy. The new analogs exhibited selective activity in stimulating intestinal calcium transport while having little or no activity in mobilizing bone calcium. They also showed HL-60-differentiating activity equal to or 10 times lower than that of 1 alpha,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/jm00048a009

文献信息

• Synthesis and Biological Activity of 2-Hydroxy and 2-Alkoxy Analogs of 1.alpha.,25-Dihydroxy-19-norvitamin D3
  作者：Rafal R. Sicinski、Kato L. Perlman、Hector F. DeLuca

  DOI：10.1021/jm00048a009

  日期：1994.10

  1 alpha,2 alpha,25 Trihydroxy-19-norvitamin D-3, 1 alpha,2 beta,25-trihydroxy-19-norvitamin D-3, and their alkoxy analogs were efficiently prepared in a convergent synthesis, starting with (-)-quinic acid and a Windaus-Grundmann type ketone. Configurations of the A-ring fragment substituents were determined by H-1,H-1 COSY 2D spectra and H-1 NOE difference spectroscopy. The new analogs exhibited selective activity in stimulating intestinal calcium transport while having little or no activity in mobilizing bone calcium. They also showed HL-60-differentiating activity equal to or 10 times lower than that of 1 alpha,25-dihydroxyvitamin D-3.