ethyl N-benzylidene-2-amino-4,4-bis(diethoxyphosphoryl)butyrate | 120355-29-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-benzylidene-2-amino-4,4-bis(diethoxyphosphoryl)butyrate
• 英文别名: Ethyl 2-(benzylideneamino)-4,4-bis(diethoxyphosphoryl)butanoate
• CAS: 120355-29-5
• 化学式: C₂₁H₃₅NO₈P₂
• 分子量: 491.458
• InChiKey: PUJGLQAKSNHEMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl N-benzylidene-2-amino-4,4-bis(diethoxyphosphoryl)butyrate 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 0.5h， 以95%的产率得到ethyl 2-amino-4,4-bis(diethoxyphosphoryl)butyrate
  参考文献：
  名称：

  Synthesis of Novel Functionalizedgem-Bisphosphonates

  摘要：

  卡宾阴离子对四乙基乙烯基双磷酸酯的Michael型加成可获得功能化的gem-双磷酸盐，这在骨组织治疗中可能具有潜在用途。

  DOI：

  10.1055/s-1991-26539
• 作为产物：
  描述：

  tetraethyl 2-methoxyethylenebisphosphonate 在 4 A molecular sieve 、 sodium ethanolate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.5h， 生成 ethyl N-benzylidene-2-amino-4,4-bis(diethoxyphosphoryl)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

文献信息

• Synthesis of Novel Functionalized<i>gem</i>-Bisphosphonates
  作者：Georges Sturtz、Joël Guervenou

  DOI：10.1055/s-1991-26539

  日期：——

  Michael-type addition of carbanions to tetraethyl ethylidenebisphosphonate affords functionalized gem-bisphosphonates, which are potentially useful in the therapy of bone tissues.

  卡宾阴离子对四乙基乙烯基双磷酸酯的Michael型加成可获得功能化的gem-双磷酸盐，这在骨组织治疗中可能具有潜在用途。
• Synthesis and In vitro characterization of a tissue-Selective fullerene: vectoring C60(OH)16AMBP to mineralized bone
  作者：K Gonzalez

  DOI：10.1016/s0968-0896(02)00049-4

  日期：2002.6

  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.