[(E,3S)-1-[(1R,2R,5R)-2-[(Z)-7-[tert-butyl(diphenyl)silyl]oxy-7-oxohept-2-enyl]-5-hydroxy-3-oxocyclopentyl]oct-1-en-3-yl] 4-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoate | 241472-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(E,3S)-1-[(1R,2R,5R)-2-[(Z)-7-[tert-butyl(diphenyl)silyl]oxy-7-oxohept-2-enyl]-5-hydroxy-3-oxocyclopentyl]oct-1-en-3-yl] 4-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoate
• CAS: 241472-13-9
• 化学式: C₇₃H₈₄O₁₂P₂Si
• 分子量: 1243.5
• InChiKey: VDPBETHGJLLFOC-SXOYCFEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.26
• 重原子数：
  88.0
• 可旋转键数：
  33.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160.96
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(E,3S)-1-[(1R,2R,5R)-2-[(Z)-7-[tert-butyl(diphenyl)silyl]oxy-7-oxohept-2-enyl]-5-hydroxy-3-oxocyclopentyl]oct-1-en-3-yl] 4-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到(Z)-7-[(1R,2R,3R)-2-[(E,3S)-3-[4-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoyl]oxyoct-1-enyl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid
  参考文献：
  名称：

  Prostaglandin E2-bisphosphonate conjugates: potential agents for treatment of osteoporosis

  摘要：

  Conjugates of bisphosphonates (potential bone resorption inhibitors) and prostaglandin E-2 (a bone formation enhancer) were prepared and evaluated for their ability to bind to bone and to liberate, enzymatically, free PGE(2). The conjugate 3, an amide at C-1 of PGE(2) proved to be too stable in vivo while conjugate 6, a thioester, was too labile. Several PGE(2), C-15 ester-linked conjugates (18, 23, 24 and 31) were prepared and conjugate 23 was found to bind effectively to bone in vitro and in vivo and to liberate PGE(2) at an acceptable rate. A 4-week study in a rat model of osteoporosis showed that 23 was better tolerated and more effective as a bone growth stimulant than daily maximum tolerated doses of free PGE(2). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00045-0
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 在 lithium hydroxide 、 草酰氯 、 sodium hydride 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 [(E,3S)-1-[(1R,2R,5R)-2-[(Z)-7-[tert-butyl(diphenyl)silyl]oxy-7-oxohept-2-enyl]-5-hydroxy-3-oxocyclopentyl]oct-1-en-3-yl] 4-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoate
  参考文献：
  名称：

  Prostaglandin E2-bisphosphonate conjugates: potential agents for treatment of osteoporosis

  摘要：

  Conjugates of bisphosphonates (potential bone resorption inhibitors) and prostaglandin E-2 (a bone formation enhancer) were prepared and evaluated for their ability to bind to bone and to liberate, enzymatically, free PGE(2). The conjugate 3, an amide at C-1 of PGE(2) proved to be too stable in vivo while conjugate 6, a thioester, was too labile. Several PGE(2), C-15 ester-linked conjugates (18, 23, 24 and 31) were prepared and conjugate 23 was found to bind effectively to bone in vitro and in vivo and to liberate PGE(2) at an acceptable rate. A 4-week study in a rat model of osteoporosis showed that 23 was better tolerated and more effective as a bone growth stimulant than daily maximum tolerated doses of free PGE(2). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00045-0