(20S)-20-iodomethyl-2β-methoxy-pregn-5-en-1α,3α-diol | 184360-07-4

• 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: (20S)-20-iodomethyl-2β-methoxy-pregn-5-en-1α,3α-diol
• CAS: 184360-07-4
• 化学式: C₂₃H₃₇IO₃
• 分子量: 488.449
• InChiKey: QPOYBHUOWZMPFI-HIXTZJONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  、 (20S)-20-iodomethyl-2β-methoxy-pregn-5-en-1α,3α-diol 在 manganese(II) iodide 、 盐酸 作用下， 生成 (R)-6-((1R,2R,3S,8S,9S,10R,13R,14S,17R)-1,3-Dihydroxy-2-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-heptanoic acid
  参考文献：
  名称：

  Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3

  摘要：

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00120-1
• 作为产物：
  描述：

  (20S)-20-(p-toluenesulfonyloxymethyl)pregna-1,5-dien-3α-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 对甲苯磺酸 、 sodium iodide 作用下， 以 氯仿 、 丙酮 、 甲苯 为溶剂， 反应 7.0h， 生成 (20S)-20-iodomethyl-2β-methoxy-pregn-5-en-1α,3α-diol
  参考文献：
  名称：

  Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3

  摘要：

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00120-1