(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 | 241472-14-0

• 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: (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
• CAS: 241472-14-0
• 化学式: C₅₇H₆₆O₁₂P₂
• 分子量: 1005.09
• InChiKey: GSSUIERTPRMDMK-IZVKQCRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.24
• 重原子数：
  71.0
• 可旋转键数：
  30.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171.96
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (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 在 palladium on activated charcoal 1,4-环己二烯 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 4.5h， 以76%的产率得到(Z)-7-[(1R,2R,3R)-2-[(E,3S)-3-[4-(2,2-diphosphonoethyl)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-[2,2-bis[bis(phenylmethoxy)phosphoryl]ethyl]benzoyl chloride 在 盐酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (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