4-mercaptobutane-1,1-diphosphonic acid | 107092-04-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 4-mercaptobutane-1,1-diphosphonic acid
• 英文别名: (1-Phosphono-4-sulfanylbutyl)phosphonic acid
• CAS: 107092-04-6
• 化学式: C₄H₁₂O₆P₂S
• 分子量: 250.149
• InChiKey: ZUDBVMDPDRCVHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-mercaptobutane-1,1-diphosphonic acid 、 tert-butyldiphenylsilyl (Z)-7-((1R,2R,3R)-2-((S,E)-3-(2-bromoacetoxy)oct-1-en-1-yl)-3-hydroxy-5-oxocyclopentyl)hept-5-enoate 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (Z)-7-[(1R,2R,3R)-2-[(E,3S)-3-[2-(4,4-diphosphonobutylsulfanyl)acetyl]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：

  tetraisopropyl 4-acetylthiobutane-1,1-diphosphonate 在 盐酸 作用下， 反应 6.0h， 以98%的产率得到4-mercaptobutane-1,1-diphosphonic 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

文献信息

• Prostaglandin E2-bisphosphonate conjugates: potential agents for treatment of osteoporosis
  作者：Laurent Gil、Yongxin Han、Evan E. Opas、Gideon A. Rodan、Réjean Ruel、J.Gregory Seedor、Peter C. Tyler、Robert N. Young

  DOI：10.1016/s0968-0896(99)00045-0

  日期：1999.5

  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.