1,4,8,11-tetrakis(2-carboxyethyl)-1,4,8,11-tetraazacyclotetradecane | 174025-02-6

• 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: 1,4,8,11-tetrakis(2-carboxyethyl)-1,4,8,11-tetraazacyclotetradecane
• 英文别名: 1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrapropionic acid；1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrapropionicacid；1,4,8,11-tetraazatetradecane-1,4,8,11-tetrapropionic acid；3-[4,8,11-Tris(2-carboxyethyl)-1,4,8,11-tetrazacyclotetradec-1-yl]propanoic acid
• CAS: 174025-02-6
• 化学式: C₂₂H₄₀N₄O₈
• 分子量: 488.582
• InChiKey: SOUJYUTZZAWCOV-UHFFFAOYSA-N

物化性质

• 沸点：
  756.4±60.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -10.3
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  europium(III) nitrate hexahydrate 、 1,4,8,11-tetrakis(2-carboxyethyl)-1,4,8,11-tetraazacyclotetradecane 在 AcOH 、 AcONa 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Prediction of the Coordination Scheme of Lanthanide N-Tetrasubstituted Tetraazamacrocycles:  An X-ray Crystallography and Molecular Modeling Study

  摘要：

  The synthesis and characterization of three lanthanide (Ce, Gd, Eu) complexes with the 1,4,8,11-tetrakis-(2-carboxyethyl) -1,4,8,11-tetraazacyclotetradecane ligand (TETP) are described. Crystal structures of [Ce(H2TETP)](OH)(H2O) . 10H(2)O (1), [Gd(H3TETP)](OH)(2)(H2O)(2) . 3H(2)O (2), and [Eu(H3TETP)](OH)(2)(H2O)(2) . 3H(2)O (3) are reported. Crystaldata: (1) monoclinic, C2/c, a = 29.523(4) Angstrom, b = 17.492(3) Angstrom, c = 8.509(1) Angstrom, beta = 98.72(1)degrees, V = 4344(1) Angstrom(3), Z = 4, R(\F\) = 0.057 for 2329 data (I/sigma(I) greater than or equal to 3), and 213 parameters; (2) monoclinic, C2/c, a = 15.378(2) Angstrom, b = 14.172(2) Angstrom, c = 14.264(2) Angstrom, beta = 99.10(1)degrees, V = 3069.5(7) Angstrom(3), Z = 4, R(\F\) = 0.075 for 1147 data (I/sigma(I) greater than or equal to 3), and 213 parameters; (3) monoclinic, C2/c, a = 15.32(1) Angstrom, b = 14.19(1) Angstrom, c = 14.130(3)Angstrom, beta = 99.41(3)degrees, V = 3031(3) Angstrom(3), Z = 4, R(\F\) = 0.085 for 1133 data (I/sigma(I) greater than or equal to 3) and 98 parameters. Complexes and 98 parameters. Complexes 2 and 3 are isotypes. In the three complexes, the centrosymmetric TETP macrocycle possesses a [3434] conformation; two propionate arms are extended, and the others are folded toward two protonated nitrogen atoms. The lanthanide coordination mode with the TETP ligand does not occur via the four nitrogen atom ring but only through carboxylic oxygen atoms belonging to four different ligands. Moreover, the four functionalized chains of the Ligand are involved in the coordination polyhedron of the gadolinium and europium ions, but only extended propionate arms of TETP take part in the cerium ion coordination polyhedron, one of the oxygen atoms of asymmetric unit being bidentate between two metallic ions. In order to better understand the reactivity and the coordination scheme observed for these complexes, a theoretical study has been carried out using the molecular electrostatic potential as a tool to predict sites of the ligands where electrophilic attack should take place. The overall good agreement between calculated and observed structures permits us to explain the coordination scheme of this new class of complexes.

  DOI：

  10.1021/ic960934h
• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 1,4,8,11-tetrakis(2-carboxyethyl)-1,4,8,11-tetraazacyclotetradecane
  参考文献：
  名称：

  新型 Tetrakis N-取代四氮杂大环的合成

  摘要：

  摘要 实现了新型四氮杂四氮杂大环化合物的合成。在四酰氨基类似物的情况下，最好的产率是通过在双相系统中使用 Schotten-Bauman 反应类型获得的。在四-N-ω 烷基羧酸酯的情况下，描述了导致所需四N-取代衍生物的最佳实验条件。

  DOI：

  10.1080/00397919808005724

文献信息

• COMPOUND FOR BONE SCANNING AND USE THEREOF
  申请人：TAIWAN HOPAX CHEMS. MFG. CO., LTD.

  公开号：US20160304545A1

  公开（公告）日：2016-10-20

  The disclosure provides a compound comprising bisphosphonate functional group and chelating agent. The bisphosphonate functional group part has high affinity for bone tissue, and the chelating agent part has high affinity for metal tracer such as radioisotope. The disclosed compound could be rapidly adsorbed onto the bone surface, and could steady emit ionizing radiation. Therefore, the disclosed compound is suitable for bone scanning technology to find abnormalities in bone.

  该披露提供了一种包含双膦酸盐功能基团和螯合剂的化合物。双膦酸盐功能基团部分具有高亲和力与骨组织结合，而螯合剂部分具有高亲和力与金属示踪剂如放射性同位素结合。所披露的化合物可以迅速吸附到骨表面，并能稳定地发射电离辐射。因此，该披露的化合物适用于骨扫描技术，用于发现骨骼中的异常。
• A New Versatile Synthesis of N,N′,N″,N″′-Tetra-(2-carboxyethyl)-and N,N′,N″,N″′-Tetra-(3-aminopropyl)-tetraazacycloalkanes by Michael Addition of Polyazacycloalkanes to Acrylic Acid and Acrylonitrile
  作者：C. Gros、H. Chollet、A. K. Mishra、R. Guilard

  DOI：10.1080/00397919608003860

  日期：1996.1

  convenient one step synthesis of N,N′,N″,N″′-tetra-(2-carboxyethyl)-tetraazacycloalkanes is reported. These compounds are synthesized by Michael addition of tetraazacycloalkanes to acrylic acid. The same Michael addition of tetraazacycloalkanes to an excess of acrylonitrile also leads to the corresponding tetracyanoethylated derivatives. The reduction of such tetracyanoethylated compounds is a new way of preparation

  摘要 报道了一种顺利、方便地一步合成 N,N',N",N"'-四-(2-羧乙基)-四氮杂环烷烃的方法。这些化合物是通过四氮杂环烷烃与丙烯酸的迈克尔加成合成的。四氮杂环烷烃与过量丙烯腈的相同迈克尔加成也产生相应的四氰乙基化衍生物。此类四氰乙基化化合物的还原是制备相应伯胺的新途径。
• A novel tetrabranched neurotensin(8–13) cyclam derivative: Synthesis, 64Cu-labeling and biological evaluation
  作者：Anika Röhrich、Ralf Bergmann、Anne Kretzschmann、Steffi Noll、Jörg Steinbach、Jens Pietzsch、Holger Stephan

  DOI：10.1016/j.jinorgbio.2011.02.011

  日期：2011.6

  cyclamtetrapropionic acid 2 using 1-ethyl-3-(3-dimethylaminocarbonyl)carbodiimide-hydrochloride and N-hydroxysulfosuccinimide. The tetrameric compound 7 was synthesized by Michael addition of neurotensin(8–13) acrylamide 6 and cyclam 1. The copper(II) complexation behavior of 4, 5 and 7 was investigated by UV/visible spectrophotometry and shows that the metal center resides inside the N4 chromophore with additional

  新大环1,4,8,11-四氮杂（cyclam）被1个，2个和4个神经降压素衍生物（8-13）单元4，5和7已被合成。使用1-乙基-3-（3-二甲基氨基羰基）碳二亚胺盐酸盐和N-羟基磺基琥珀酰亚胺，通过不稳定的神经降压素（8-13）和环四丙酸2反应制备化合物4和5。四聚体化合物7是通过神经降压素（8-13）丙烯酰胺6和cyclam 1的迈克尔加成合成的。的铜（II）络合行为4，5和7用紫外/可见光分光光度法进行了研究，结果表明金属中心位于N4发色团内部，并通过悬垂臂建立了额外的顶端相互作用。具有纳摩尔神经降压素受体1结合亲和力的新型四支NT（8-13）cyclam 7在温和条件下有效地用64 Cu进行了放射性标记。64铜⊂7显示大量的cyclam作为竞争性配体的存在下缓慢transchelation，同时它完全保持在EDTA的存在下保持完整。在大鼠和小鼠中研究了64 Cu⊂7的体内行为。啮齿
• Copper(<scp>ii</scp>) chemistry of the functionalized macrocycle cyclam tetrapropionic acid
  作者：Peter Comba、Franziska Emmerling、Maik Jakob、Werner Kraus、Manja Kubeil、Michael Morgen、Jens Pietzsch、Holger Stephan

  DOI：10.1039/c2dt32356g

  日期：——

  The CuII complex of H4TETP (H4TETP = 1,4,8,11-tetraazatetradecane-1,4,8,11-tetrapropionic acid) is five-coordinate with a distorted square-pyramidal structure (τ = 0.45; i.e. the geometry is nearly half-way between square-pyramidal and trigonal-bipyramidal) and a relatively long Cu–N and a short Cu–O bond; the comparison between powder and solution electronic spectroscopy, the frozen solution EPR spectrum

  在Cu II的复杂ħ 4 TETP（H 4 TETP = 1,4,8,11- tetraazatetradecane-1,4,8,11- tetrapropionic酸）是五配位与一个扭曲的四方锥结构（τ = 0.45;即，几何形状几乎在正方形-金字塔形和三角形-双金字塔形之间；并且有一个相对较长的Cu–N和一个较短的Cu–O键；粉末和溶液电子光谱，冷冻溶液的EPR光谱和基于配体场的计算（角度重叠模型，AOM）之间的比较表明，溶液和固态结构非常相似，即该络合物的“ in-平面”和显著轴向配体与广告字段X 2 -y 2基态。因此，配体强化的结构显示出导致部分淬灭的Jahn-Teller变形和相对较低的复合物稳定性，低于相应的乙酸酯衍生的配体H 4 TETA。电位滴定法和64种Cu标记配体的生物分布证实了这一点，这表明基于H 4 TETP的系统在肝脏中的摄取显着增加。
• IGF-1R monoclonal antibodies and uses thereof
  申请人：Fusion Pharmaceuticals Inc.

  公开号：US10093741B1

  公开（公告）日：2018-10-09

  The present invention relates to conjugates including a chelating moiety of a metal complex thereof and a therapeutic or targeting moiety, methods for their production, and uses thereof.

  本发明涉及包括金属配合物的螯合基团和治疗或靶向基团的共轭物、其生产方法以及其用途。