methyl N-(2-pyrazol-1-yl)ethyliminodiacetate | 186667-01-6

• 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: methyl N-(2-pyrazol-1-yl)ethyliminodiacetate
• 英文别名: methyl N-[2-(1-pyrazolyl)ethyl]iminodiacetate；Methyl 2-[(2-methoxy-2-oxoethyl)-(2-pyrazol-1-ylethyl)amino]acetate
• CAS: 186667-01-6
• 化学式: C₁₁H₁₇N₃O₄
• mdl: MFCD18046262
• 分子量: 255.274
• InChiKey: UWXNQORGCIYEML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-(2-pyrazol-1-yl)ethyliminodiacetate 在 sodium hydroxide 作用下， 反应 24.0h， 生成 N-(2-pyrazol-1-yl)ethyliminodiacetic acid sodium salt
  参考文献：
  名称：

  N-2-(Azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging

  摘要：

  The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T-1 and T-2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T-2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00273-9
• 作为产物：
  描述：

  亚氨基二乙酸二甲酯 、 1-(2-溴乙基)-1H-吡唑 反应 2.5h， 以55%的产率得到methyl N-(2-pyrazol-1-yl)ethyliminodiacetate
  参考文献：
  名称：

  N-2-(Azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging

  摘要：

  The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T-1 and T-2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T-2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00273-9

文献信息

• COMPLEXONES WITH THE STRUCTURE OF N-2-(AZOL-1(2)-YL)ETHYLIMINODIACETIC ACIDS, SYNTHESIS, ANALYTICAL STUDY AND BIOLOGICAL APPLICATIONS
  申请人：UNIVERSIDAD NACIONAL DE EDUCACION A DISTANCIA

  公开号：EP0790241A1

  公开（公告）日：1997-08-20

  Complexones having the structure of N-2-(azol-1(2)-yl(ethyl-iminodiacetic acids, synthesis, analytical study and biological applications, characterized by their complexing capacity over Ca2+, Mg2+ ions and other bivalent cations, lanthanides and transition metals. In the formula azolN-CH2-CH2-N(CH2-CO2R)2 (I), azol is pirazol; 3,5-dimethylpirazol; indazol; etc. and R is alkyl or H or Na. The compounds having the general formula (I), are obtained by an alkylation reaction of methyl iminodiacetate with N-bromoethylazols and further hydrolysis in acid or basic medium. The process may be modified by alternative synthetic processes which involve N-aminoethylazols as starting materials or the use of cyclization processes in the preparation of N-substituted azol. They can be applied in spectroscopy and nuclear magnetic resonance (NMR) imaging of hydrogen or other nuclei as extrinsic probes of Ca2+, Mg2+ or other metal ions and as contrast agents, in solutions, biological extracts, tissues, entire animals and human beings.

  具有 N-2-(azol-1(2)-yl(ethyl-iminodiacetic acids)结构的络合剂的合成、分析研究和生物应用，其特点是对 Ca2+、Mg2+ 离子和其他二价阳离子、镧系元素和过渡金属的络合能力。在式 azolN-CH2-CH2-N(CH2-CO2R)2 (I) 中，azol 是吡唑；3,5-二甲基吡唑；吲唑等，R 是烷基或 H 或 Na。具有通式（I）的化合物是通过亚氨基二乙酸甲酯与 N-溴乙基唑的烷基化反应，并在酸性或碱性介质中进一步水解得到的。该工艺可通过其他合成工艺进行改良，如将 N-氨基乙基偶氮酚作为起始原料，或在制备 N-取代偶氮酚时使用环化工艺。它们可作为 Ca2+、Mg2+ 或其他金属离子的外在探针和造影剂，应用于溶液、生物提取物、组织、整个动物和人体中氢或其他核的光谱学和核磁共振（NMR）成像。
• N-2-(Azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging
  作者：Pilar López、Christa G Seipelt、Patrick Merkling、Laszlo Sturz、José Álvarez、Andreas Dölle、Manfred D Zeidler、Sebastián Cerdán、Paloma Ballesteros

  DOI：10.1016/s0968-0896(98)00273-9

  日期：1999.3

  The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T-1 and T-2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T-2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. (C) 1999 Elsevier Science Ltd. All rights reserved.