ethyl 2-amino-4,4-bis(diethoxyphosphoryl)butyrate | 120355-30-8

• 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 2-amino-4,4-bis(diethoxyphosphoryl)butyrate
• 英文别名: Ethyl 2-amino-4,4-bis(diethoxyphosphoryl)butanoate
• CAS: 120355-30-8
• 化学式: C₁₄H₃₁NO₈P₂
• 分子量: 403.35
• InChiKey: LVQOUFAZHHWKAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4,4-bis(diethoxyphosphoryl)butyrate 在 氢氧化钾 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.25h， 生成 acide 2-N-(t-butoxycarbonyl)amino-4,4-bis(diethylphosphono)butanoique
  参考文献：
  名称：

  Guervenou, J.; Sturtz, G., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 88, # 1-4, p. 1 - 14

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-双(二乙氧基磷酰基)乙烯 在 sodium ethanolate 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 0.75h， 生成 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

文献信息

• 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。
• A study of the delivery-targeting concept applied to antineoplasic drugs active on human osteosarcoma. I. Synthesis and biological activity in nude mice carrying human osteosarcoma xenografts of gem-bisphosphonic methotrexate analogues
  作者：G Sturtz、G Appéré、K Breistol、O Fodstad、G Schwartsmann、HR Hendriks

  DOI：10.1016/0223-5234(92)90117-j

  日期：1992.11

  With the aim of verifying the concept of osteotic vectorisation, synthesis of three methotrexate (MTX) gem-diphosphonic analogues (compounds A, B and C) was performed. These molecules were tested on BALB/c and NIH III mice previously grafted with subcutaneous implants of OHS, TTX p7 and/or TTX p11 human osteosarcoma cell lines. Antineoplasic activity of compound B and C (active compounds) was compared to the activity for MTX alone and to activity of compound A (inactive compound). Compounds B and C exhibited an increased antineoplasic activity compared to MTX alone and to compound A. At equimolar doses, compound B was found to be 5-6-fold more active than MTX given alone. We have discussed the concept of osteotic vectorisation of compound B, which could be regarded as a prodrug.
• Synthesis of gem-bisphosphonic methotrexate conjugates and their biological response towards Walker's osteosarcoma
  作者：G Sturtz、H Couthon、O Fabulet、M Mian、S Rosini

  DOI：10.1016/0223-5234(93)90043-e

  日期：1993.1
• 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.
• Fabulet, O.; Sturtz, G., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 101, # 1-4, p. 225 - 234
  作者：Fabulet, O.、Sturtz, G.

  DOI：——

  日期：——