tetraethyl 2-methoxyethylenebisphosphonate

• 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: tetraethyl 2-methoxyethylenebisphosphonate
• 英文别名: tetraethyl (2-methoxyethylene-1,1-diyl)bisphosphonate；1,1-Bis(diethoxyphosphoryl)-2-methoxyethene；1,1-bis(diethoxyphosphoryl)-2-methoxyethene
• 化学式: C₁₁H₂₄O₇P₂
• 分子量: 330.255
• InChiKey: BHTBXHPDSNGGBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl 2-methoxyethylenebisphosphonate 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以4.0 g的产率得到1,1-双(二乙氧基磷酰基)乙烯
  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：

  甲醇 、 聚合甲醛 、 亚甲基二磷酸四乙酯 在 二乙胺 作用下， 反应 24.0h， 生成 tetraethyl 2-methoxyethylenebisphosphonate
  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

• 1,3-Dipolar Cycloadditions of the Versatile Intermediate Tetraethyl Vinylidenebisphosphonate­
  作者：Sergio Szajnman、Juan Rodriguez、Mariana Ferrer-Casal、Alejandro Barboza

  DOI：10.1055/s-0033-1338498

  日期：——

  the preparation of diverse and fairly complex structures bearing the bisphosphonate moiety, which belong to a group of pharmacologically important compounds. The use of tetraethyl vinylidenebisphosphonate as a dipolarophile in 1,3-dipolar cycloaddition reactions was investigated. In particular, the cycloaddition reactions between tetraethyl vinylidenebisphosphonate and azides and nitrile oxides, and

  摘要 研究了四乙基亚乙烯基双膦酸酯在1，3-偶极环加成反应中作为亲双性物的用途。特别地，研究了在Grigg偶氮甲辛1，3-偶极环化中，四乙基亚乙烯基双膦酸酯与叠氮化物和氧化腈之间的环加成反应，以及四乙基亚乙烯基双膦酸酯的环加成反应，得到了具有双膦酸单元的高度官能化的五元环。这些简单的方法可以制备带有双膦酸酯部分的多样且相当复杂的结构，该结构属于一组具有重要药理意义的化合物。 研究了四乙基亚乙烯基双膦酸酯在1，3-偶极环加成反应中作为亲双性物的用途。特别地，研究了在Grigg偶氮甲辛1，3-偶极环化中，四乙基亚乙烯基双膦酸酯与叠氮化物和氧化腈之间的环加成反应，以及四乙基亚乙烯基双膦酸酯的环加成反应，得到了具有双膦酸单元的高度官能化的五元环。这些简单的方法可以制备带有双膦酸酯部分的多样且相当复杂的结构，该结构属于一组具有重要药理意义的化合物。
• Fullerene-based drugs targeted to bone
  申请人：——

  公开号：US20040038946A1

  公开（公告）日：2004-02-26

  A method for providing bone therapy in a patient in need of bone therapy comprises administering to the patient a pharmaceutically effective amount of a compound comprising a biologically inert carrier, a bone vector; and a therapeutic agent. The bone vector preferably comprises a bisphosphonate, the carrier preferably comprises a fullerene, and more preferably C 60 , the therapeutic agent preferably comprises fluoride.

  一种用于为需要骨疗法的患者提供骨疗法的方法，包括向患者施用含有药物有效量的化合物，该化合物包括生物惰性载体、骨向量和治疗剂。骨向量最好包括双磷酸盐，载体最好包括富勒烯，更好的是C60，治疗剂最好包括氟化物。
• [EN] FULLERENE-BASED DRUGS TARGETED TO BONE<br/>[FR] MEDICAMENTS A BASE DE FULLERENE CIBLES POUR LES OS
  申请人：UNIV WM MARSH RICE

  公开号：WO2001080898A1

  公开（公告）日：2001-11-01

  A method for providing bone therapy in a patient in need of bone therapy comprises administering to the patient a pharmaceutically effective amount of a compound comprising a biologically inert carrier, a bone vector; and a therapeutic agent. The bone vector preferably comprises a bisphosphonate, the carrier preferably comprises a fullerene, and more preferably C60, the therapeutic agent preferably comprises fluoride.
• 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.