tetraethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bisphosphonate | 227747-87-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tetraethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bisphosphonate
• CAS: 227747-87-7
• 化学式: C₄₆H₈₆O₈P₂Si₂
• 分子量: 885.303
• InChiKey: NJCLBVLRAAHCHI-JCJIBLTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.53
• 重原子数：
  58.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tetraethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bisphosphonate 在 Dowex resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以42.8%的产率得到tetraethyl [(5Z,7E,22E,24E)-(1S,3R)-1,3-dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bisphosphonate
  参考文献：
  名称：

  Synthesis and biological activities of a new series of secosteroids: vitamin D phosphonate hybrids

  摘要：

  By a structural combination of phosphonate and bisphosphonate moieties with the vitamin D skeleton a series of new vitamin D analogs was synthesized. Derivatives with 24 beta -hydroxy- or 24-keto groups exerted considerable vitamin D activities in vitro while the hypercalcemic potentials were significantly reduced as compared to 1 alpha .25-dihydroxyvitamin D-3 (calcitriol). Whereas the 24-hydroxy analogs did not influence bone formation in vivo in dosages below the hypercalcemic threshold, the 24-ketones were found to induce synthesis of new bone matrix in non-hypercalcemic doses. Vitamin D bisphosphonate hybrids, on the other hand, which did not elicit substantial vitamin D activities in vitro and tend to decrease serum calcium levels in vivo clearly induced osteoid formation in rats, indicating a mechanism of action different to calcitriol. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00148-3
• 作为产物：
  描述：

  (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-al 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 生成 tetraethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bisphosphonate
  参考文献：
  名称：

  Synthesis and biological activities of a new series of secosteroids: vitamin D phosphonate hybrids

  摘要：

  By a structural combination of phosphonate and bisphosphonate moieties with the vitamin D skeleton a series of new vitamin D analogs was synthesized. Derivatives with 24 beta -hydroxy- or 24-keto groups exerted considerable vitamin D activities in vitro while the hypercalcemic potentials were significantly reduced as compared to 1 alpha .25-dihydroxyvitamin D-3 (calcitriol). Whereas the 24-hydroxy analogs did not influence bone formation in vivo in dosages below the hypercalcemic threshold, the 24-ketones were found to induce synthesis of new bone matrix in non-hypercalcemic doses. Vitamin D bisphosphonate hybrids, on the other hand, which did not elicit substantial vitamin D activities in vitro and tend to decrease serum calcium levels in vivo clearly induced osteoid formation in rats, indicating a mechanism of action different to calcitriol. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00148-3