2-[4,10-Bis-(1,3-bis-methoxycarbonyl-propyl)-1,4,7,10-tetraaza-cyclododec-1-yl]-pentanedioic acid dimethyl ester | 357165-77-6

• 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: 2-[4,10-Bis-(1,3-bis-methoxycarbonyl-propyl)-1,4,7,10-tetraaza-cyclododec-1-yl]-pentanedioic acid dimethyl ester
• 英文别名: Dimethyl 2-[4,7-bis(1,5-dimethoxy-1,5-dioxopentan-2-yl)-1,4,7,10-tetrazacyclododec-1-yl]pentanedioate；dimethyl 2-[4,7-bis(1,5-dimethoxy-1,5-dioxopentan-2-yl)-1,4,7,10-tetrazacyclododec-1-yl]pentanedioate
• CAS: 357165-77-6
• 化学式: C₂₉H₅₀N₄O₁₂
• 分子量: 646.736
• InChiKey: FIELEUYGTYPKGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  180
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-[4,10-Bis-(1,3-bis-methoxycarbonyl-propyl)-1,4,7,10-tetraaza-cyclododec-1-yl]-pentanedioic acid dimethyl ester 在 lithium hydroxide 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 1-[2'-(4-methoxyphenylsulfonylamino)ethyl]-4,7,10-tris[(3'-carboxyl)-1'-carboxypropyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  基于可逆分子内磺酰胺连接的大环钆和铕配合物中弛豫和发光的 pH 依赖性调节

  摘要：

  已经制备了一系列大环 Eu、Gd 和 Tb 复合物，其中 β-芳基磺酰胺氮的分子内连接呈现 pH 依赖性，导致镧系元素中心的水合状态 q 发生变化。在基于 DO3A 的复合物中，芳基磺酰胺部分中 p 取代基的变化决定了表观质子化常数 log K(MLH)，-CF(3)、-Me 和 -OMe 取代基的值为 5.7、6.4 和 6.7 ， 分别。引入三个 β-羧基烷基取代基、α 到三个环氮，可抑制添加蛋白质对结合水的置换，并抑制内源性阴离子（乳酸、HCO(3)(-)）的分子间结合。对 Eu 配合物形式和强度的 pH 依赖性的测量表明，分子内羧酸盐配位是竞争性发生的。这可以通过提高磺酰胺氮上的电子密度或通过将螯合环从 7--8 扩大来减少。pH 范围 8--5 中弛豫度变化的放大发生在蛋白质结合上，并且在 pH 值 7.4--6.8 范围内，[Gd.3a]（298 K，65.6 MHz）在 50

  DOI：

  10.1021/ja0103647
• 作为产物：
  描述：

  (S)-2-bromopentanedioic acid dimethyl ester 、 轮环藤宁 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以39%的产率得到2-[4,10-Bis-(1,3-bis-methoxycarbonyl-propyl)-1,4,7,10-tetraaza-cyclododec-1-yl]-pentanedioic acid dimethyl ester
  参考文献：
  名称：

  [EN] 1 , 4 -BIS (CARBOXYMETHYL) -6- ' BIS ( CARBOXYMETHYL) AMINO ! -6 -METHYL- PERHYDRO-1 , 4 DIAZEPINE (AAZTA) DERIVATIVES AS LIGANDS IN HIGH RELAXIVITY CONTRAST AGENTS FOR USE IN MAGNETIC RESONANCE IMAGING (MRI )
  [FR] AGENTS DE CONTRASTE A RELAXIVITE ACCRUE

  摘要：

  公开号：

  WO2006002873A3

文献信息

• Contrast agents endowed with high relaxivity
  申请人：Aime Silvio

  公开号：US20110256067A1

  公开（公告）日：2011-10-20

  The present invention relates to a novel class of paramagnetic ion-based contrast agents of formula (I), wherein a chelating backbone moiety is highly functionalized by the presence of one or more polyhydroxylated chain, that show a pharmacokinetic profile analogous to that of the commonly used T1-general extravascular agents (NSA) but are further characterized by a higher relaxivity.

  本发明涉及一种新型的基于顺磁离子的对比剂类别，其化学式为(I)，其中螯合骨架部分通过一个或多个多羟基链的存在高度功能化，表现出与常用的T1通用非血管外用对比剂(NSA)相似的药代动力学特征，但具有更高的弛豫度。
• The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission
  作者：James I. Bruce、Rachel S. Dickins、Linda J. Govenlock、Thorfinnur Gunnlaugsson、Stefan Lopinski、Mark P. Lowe、David Parker、Robert D. Peacock、Justin J. B. Perry、Silvio Aime、Mauro Botta

  DOI：10.1021/ja001797x

  日期：2000.10.1

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.
• US8540966B2
  申请人：——

  公开号：US8540966B2

  公开（公告）日：2013-09-24
• [EN] 1 , 4 -BIS (CARBOXYMETHYL) -6- ' BIS ( CARBOXYMETHYL) AMINO ! -6 -METHYL- PERHYDRO-1 , 4 DIAZEPINE (AAZTA) DERIVATIVES AS LIGANDS IN HIGH RELAXIVITY CONTRAST AGENTS FOR USE IN MAGNETIC RESONANCE IMAGING (MRI )<br/>[FR] AGENTS DE CONTRASTE A RELAXIVITE ACCRUE
  申请人：BRACCO IMAGING SPA

  公开号：WO2006002873A3

  公开（公告）日：2007-05-10
• pH-Dependent Modulation of Relaxivity and Luminescence in Macrocyclic Gadolinium and Europium Complexes Based on Reversible Intramolecular Sulfonamide Ligation
  作者：Mark P. Lowe、David Parker、Ofer Reany、Silvio Aime、Mauro Botta、Giancarlo Castellano、Eliana Gianolio、Roberto Pagliarin

  DOI：10.1021/ja0103647

  日期：2001.8.1

  A series of macrocyclic Eu, Gd, and Tb complexes has been prepared in which the intramolecular ligation of a beta-arylsulfonamide nitrogen is rendered pH-dependent, giving rise to changes in the hydration state, q, at the lanthanide center. In complexes based on DO3A, variation of the p-substituent in the arylsulfonamide moiety determines the apparent protonation constant log K(MLH) with values of

  已经制备了一系列大环 Eu、Gd 和 Tb 复合物，其中 β-芳基磺酰胺氮的分子内连接呈现 pH 依赖性，导致镧系元素中心的水合状态 q 发生变化。在基于 DO3A 的复合物中，芳基磺酰胺部分中 p 取代基的变化决定了表观质子化常数 log K(MLH)，-CF(3)、-Me 和 -OMe 取代基的值为 5.7、6.4 和 6.7 ， 分别。引入三个 β-羧基烷基取代基、α 到三个环氮，可抑制添加蛋白质对结合水的置换，并抑制内源性阴离子（乳酸、HCO(3)(-)）的分子间结合。对 Eu 配合物形式和强度的 pH 依赖性的测量表明，分子内羧酸盐配位是竞争性发生的。这可以通过提高磺酰胺氮上的电子密度或通过将螯合环从 7--8 扩大来减少。pH 范围 8--5 中弛豫度变化的放大发生在蛋白质结合上，并且在 pH 值 7.4--6.8 范围内，[Gd.3a]（298 K，65.6 MHz）在 50