ethyl 4,4-bis(diethoxyphosphoryl)-2-(1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyrate | 371124-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ethyl 4,4-bis(diethoxyphosphoryl)-2-(1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyrate
• CAS: 371124-77-5
• 化学式: C₇₆H₃₁NO₉P₂
• 分子量: 1164.03
• InChiKey: ONPSDCZBTFGDBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.22
• 重原子数：
  88.0
• 可旋转键数：
  16.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  126.46
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-bis(diethoxyphosphoryl)-2-(1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyrate 在 碘代三甲硅烷 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以90%的产率得到4,4-bisphosphono-2-(1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyric acid
  参考文献：
  名称：

  Synthesis and In vitro characterization of a tissue-Selective fullerene: vectoring C60(OH)16AMBP to mineralized bone

  摘要：

  A tissue-vectored bisphosphonate fullerene, C-60(OH)(16)AMBP [4,4-bisphosphono-2-(polyhydroxyl-1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyric acid], designed to target bone tissue has been synthesized and evaluated in vitro. An amide bisphosphonate addend, in conjunction with multiple hydroxyl groups, confers a strong affinity for the calcium phosphate mineral hydroxyapatite of bone. Constant composition crystal growth studies indicate that C60(OH)(16)AMBP reduces hydroxyapatite mineralization by 50% at a concentration of 1 muM, following a non-Langmuirian mechanism. Parallel studies with C-60(OH)(30) also indicate an affinity for hydroxyapatite, but at a reduced level (28% crystal growth rate reduction at 1 muM) compared with C-60(OH)(16)AM BP. This study is the first to demonstrate that a fullerene-based material can be successfully targeted to a selected tissue as a step toward the development of such materials for medical purposes, in general. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00049-4
• 作为产物：
  描述：

  1,1-双(二乙氧基磷酰基)乙烯 在 sodium ethanolate 、 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 为溶剂， 反应 121.0h， 生成 ethyl 4,4-bis(diethoxyphosphoryl)-2-(1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyrate
  参考文献：
  名称：

  Synthesis and In vitro characterization of a tissue-Selective fullerene: vectoring C60(OH)16AMBP to mineralized bone

  摘要：

  A tissue-vectored bisphosphonate fullerene, C-60(OH)(16)AMBP [4,4-bisphosphono-2-(polyhydroxyl-1,2-dihydro-1,2-methanofullerene[60]-61-carboxamido)butyric acid], designed to target bone tissue has been synthesized and evaluated in vitro. An amide bisphosphonate addend, in conjunction with multiple hydroxyl groups, confers a strong affinity for the calcium phosphate mineral hydroxyapatite of bone. Constant composition crystal growth studies indicate that C60(OH)(16)AMBP reduces hydroxyapatite mineralization by 50% at a concentration of 1 muM, following a non-Langmuirian mechanism. Parallel studies with C-60(OH)(30) also indicate an affinity for hydroxyapatite, but at a reduced level (28% crystal growth rate reduction at 1 muM) compared with C-60(OH)(16)AM BP. This study is the first to demonstrate that a fullerene-based material can be successfully targeted to a selected tissue as a step toward the development of such materials for medical purposes, in general. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00049-4