diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate | 227747-67-3

• 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: diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate
• CAS: 227747-67-3
• 化学式: C₄₁H₇₃O₆PSi₂
• 分子量: 749.172
• InChiKey: MHSHPPIXLZSHGQ-SAQJEHAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.21
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate 在 正丁基锂 、 Dowex resin 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(1Z,3E,5R)-5-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-1-diethoxyphosphorylhexa-1,3-dien-2-yl] diethyl phosphate
  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)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secopregna-5,7,10(19)-triene-20-carbaldehyde 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate
  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