1,4,7-triazacyclononane-1,4,7-tripropionic acid | 112995-07-0

• 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: 1,4,7-triazacyclononane-1,4,7-tripropionic acid
• 英文别名: 3-[4,7-Bis(2-carboxyethyl)-1,4,7-triazonan-1-yl]propanoic acid
• CAS: 112995-07-0
• 化学式: C₁₅H₂₇N₃O₆
• 分子量: 345.396
• InChiKey: XTBYGWFSZYYULT-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161 °C
• 沸点：
  617.6±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -8.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,4,7-triazacyclononane-1,4,7-tripropionic acid 、 copper(II) perchlorate hexahydrate 以 水 为溶剂， 反应 24.0h， 以72%的产率得到[Cu(tacndp)]ClO₄*H₂O
  参考文献：
  名称：

  带有丙酸悬臂的三氮杂环壬烷衍生物的杂金属和均金属配位聚合物的制备、晶体结构和磁性能

  摘要：

  两种 Cu(II)–Na(I) 异金属配位聚合物 [Cu2Na5(tacntp)2(H2O)9](ClO4)3·2H2O (1) 和 [Cu2Na5(tacntp)2(H2O)9](ClO4) 3·2H2O (2) 由Cu(II) 盐和三取代的N-丙酸官能化配体构成，即1,4,7-三氮杂环壬烷-1,4,7-三丙酸(tacntpH3)。在配合物 1 中，Na+ 离子充当节点，被六个 [Cu(tacntp)]- 部分包围，形成二维配位聚合物。在配合物 2 中，Na+ 离子被悬垂的羧酸盐基团和水配体桥接，得到一维 Na-O 无机聚合物带，通过连接 [Cu(tacntp)]- 单元扩展成复杂的二维异金属阵列。两种结构之间的差异与反应介质中存在的 Na+ 离子的量有关。在进一步的实验中，三取代的前配体 tacntpH3 经历了三个悬臂之一的水热 Cu(II) 诱导的裂解，所得双取代的前配体 tacndpH2

  DOI：

  10.1007/s11243-016-0104-x
• 作为产物：
  描述：

  trimethyl 3,3′,3″-(1,4,7-triazonane-1,4,7-triyl)tri-propionate 在 盐酸 作用下， 以 水 为溶剂， 反应 20.0h， 以44%的产率得到1,4,7-triazacyclononane-1,4,7-tripropionic acid
  参考文献：
  名称：

  了解电子自旋弛豫对具有三氮杂环壬烷衍生物的 Mn(II) 配合物弛豫率的影响

  摘要：

  研究顺磁性 Mn(II) 复合物诱导的水1 H 核的弛豫对于了解控制用于诊断磁共振成像 (MRI) 的造影剂效率的机制很重要。在此，设计了一系列包含不同悬臂的潜在六齿三氮杂环壬烷 (TACN) 衍生物，通过结合1 H NMR 弛豫和理论计算来探索相应 Mn(II) 配合物中电子自旋的弛豫。这些配体包括 1,4,7-三氮杂环壬烷-1,4,7-三乙酸 (H 3 NOTA) 和三个衍生物，其中乙酸基被磺酰胺 (H 3 NO2ASAm)、酰胺 (H 2 NO2AM) 或吡啶基（H2 NO2APy) 吊坠。还研究了包含三个丙酸悬垂臂（H 3 NOTPrA）的 H 3 NOTA类似物。含有两个乙酸酯基团和一个磺酰胺悬臂 [Mn(NO2ASAm)] -的衍生物的 X 射线结构证明了配体与金属离子的六配位，配位多面体接近三棱柱。所有配合物在 20 MHz 和 25 °C (1.1–1.3 mM –1 s –1)

  DOI：

  10.1021/acs.inorgchem.1c02057

文献信息

• Complexes of cyclic polyaza chelators with cations of alkaline earth metals for enhanced biological activity
  申请人：Winchell S. Harry

  公开号：US20050112066A1

  公开（公告）日：2005-05-26

  Cyclic polyaza chelators that possess high affinity and specificity for first transition series metal cations exhibit an unanticipated improvement in biological activity when administered as complexes with cations of the alkaline earth metals, Ca(II) and Mg(II), most notably Ca(II). By virtue of this improvement, these complexes are particularly effective in the treatment of pathological conditions, including ischemia and ischemia-reperfusion injury.

  具有高亲和力和特异性的环状多氮螯合剂，当与碱土金属阳离子的络合物一起给药时，表现出生物活性的意外改善，其中以Ca(II)和Mg(II)的络合物最为显著，尤其是Ca(II)。由于这种改善，这些络合物在治疗病理条件，包括缺血和缺血再灌注损伤方面特别有效。
• Synthesis, Characterization and Antimicrobial Activity of Triazamacrocyclic Based Polymeric Ligand and its Polymer-Metal Complexes
  作者：Saad M. Alshehri、Eida Al-Farraj、Norah Alhokbany、Tansir Ahamad

  DOI：10.14233/ajchem.2015.18086

  日期：——

  A triazamacrocyclic-based polymeric ligand (poly-H3L) was synthesized via polycondensation of 1,4,7-triazacyclonone-1,4,7-tripropionic acid (NOTPA) and ethylenediamine and polymer-metal complexes were prepared with Cu(II), Zn(II), In(III) and Ga(III) ions. All of the synthesized polymers were characterized by elemental, spectral and thermal analyses. The elemental and spectral data revealed that the poly-HLM(II) are five-coordinate complexes in which the metals are coordinated to three nitrogen atoms in the macrocycle and are coordinate covalently bound to two amide groups. However, the poly-LM(III) are six-coordinate complexes. The thermal kinetics, such as the activation energy and the thermodynamic parameters of the synthesized polymers were evaluated during pyrolysis using the Coats-Redfern equation. In addition, the antimicrobial activity of the synthesized polymers was evaluated against several microorganisms using agar-well diffusion methods. Among all of the polymer-metal complexes, the antimicrobial activity of the Cu(II)-chelated polymer exhibited the largest zone of inhibition.

  通过1,4,7-三氮杂环酮-1,4,7-三丙酸(NOTPA)和乙二胺的缩聚合成了基于三氮杂大环的聚合物配体(poly-H3L)，并用Cu(II)制备了聚合物-金属配合物， Zn(II)、In(III) 和 Ga(III) 离子。所有合成的聚合物均通过元素、光谱和热分析进行表征。元素和光谱数据表明，聚HLM(II)是五配位络合物，其中金属与大环中的三个氮原子配位，并与两个酰胺基团配位共价结合。然而，poly-LM(III) 是六配位配合物。使用 Coats-Redfern 方程评估热解过程中的热动力学，例如合成聚合物的活化能和热力学参数。此外，使用琼脂井扩散方法评估了合成聚合物针对几种微生物的抗菌活性。在所有聚合物-金属配合物中，Cu(II)-螯合聚合物的抗菌活性表现出最大的抑制区。
• Neuroprotection and cardioprotection afforded by chelators with high affinity and specificity for cations of first transition series elements
  申请人：CONCAT, LTD. a California Limited Partnership

  公开号：US20040006055A1

  公开（公告）日：2004-01-08

  Compounds that demonstrate chelation affinity and selectivity for first transition series elements are administered to patients suffering from such conditions as ischemia, prolonged seizures and trauma to provide neuroprotection, cardioprotection, or both. These compounds when administered form complexes with chelatable iron and copper cations and thereby mitigate the ability of these cations to catalyze Haber-Weiss reactions that form toxic hydroxy free radicals that cause tissue injury. These compounds also form complexes with chelatable zinc cations thereby inhibiting the cytotoxicity associated with excess chelatable zinc.

  表现出对第一过渡系列元素具有螯合亲和力和选择性的化合物被用于治疗患有缺血、持续性癫痫和创伤等疾病的患者，以提供神经保护、心脏保护或两者兼而有之。这些化合物在被给药时会与可螯合的铁和铜阳离子形成络合物，从而减轻这些阳离子催化哈伯-魏斯反应的能力，这些反应会产生导致组织损伤的有毒羟自由基。这些化合物还会与可螯合的锌阳离子形成络合物，从而抑制与过多可螯合锌相关的细胞毒性。
• Compounds with chelation affinity and selectivity for first transition series elements and their use in cosmetics and personal care products, inhibition of metalloenzymes, and inhibition of reperfusion injury
  申请人：——

  公开号：US20010041170A1

  公开（公告）日：2001-11-15

  This invention involves the use of a class of compounds with chelation affinity and selectivity for first transition series elements. Application or administration of the free or conjugated compound, or physiological salts of the free or conjugated compound, results in decrease of the bioavailability and/or chemical action of first transition series elements. These characteristics make such compounds useful in cosmetics and personal care products to decrease odor arising from microbial growth on body surfaces and in body cavities, decrease microbial growth on teeth, plaque, and gums that cause tooth decay and gum disease, inhibition of oxidative damage to the skin, inhibition of enzymatic action of metalloenzymes dependent on first transition series elements, and inhibition of reperfusion injury.

  这项发明涉及使用一类对第一过渡系列元素具有螯合亲和力和选择性的化合物。应用或给予自由或结合化合物，或自由或结合化合物的生理盐，可导致第一过渡系列元素的生物利用度和/或化学作用降低。这些特性使得这些化合物在化妆品和个人护理产品中非常有用，可减少身体表面和身体腔内微生物生长引起的气味，减少导致牙齿蛀牙和牙龈疾病的牙菌斑和牙龈微生物生长，抑制皮肤氧化损伤，抑制依赖于第一过渡系列元素的金属酶的酶促作用，以及抑制再灌注损伤。
• COMPOUNDS WITH CHELATION AFFINITY AND SELECTIVITY FOR FIRST TRANSITION SERIES ELEMENTS AND THEIR USE IN COSMETICS AND PERSONAL CARE PRODUCTS, INHIBITION OF METALLOENZYMES, AND INHIBITION OF REPERFUSION INJURY
  申请人：Concat, Ltd.

  公开号：US06387891B2

  公开（公告）日：2002-05-14

  This invention involves the use of a class of compounds with chelation affinity and selectivity for first transition series elements. Application or administration of the free or conjugated compound, or physiological salts of the free or conjugated compound, results in decrease of the bioavailability and/or chemical action of first transition series elements. These characteristics make such compounds useful in cosmetics and personal care products to decrease odor arising from microbial growth on body surfaces and in body cavities, decrease microbial growth on teeth, plaque, and gums that cause tooth decay and gum disease, inhibition of oxidative damage to the skin, inhibition of enzymatic action of metalloenzymes dependent on first transition series elements, and inhibition of reperfusion injury.

  这项发明涉及一类具有螯合亲和力和选择性的化合物，用于第一过渡系列元素。应用或给予自由或结合化合物，或自由或结合化合物的生理盐，可导致第一过渡系列元素生物利用度和/或化学作用的降低。这些特性使得这种化合物在化妆品和个人护理产品中非常有用，可减少微生物在身体表面和体腔上生长引起的气味，减少在牙齿、牙菌斑和牙龈上生长引起的龋齿和牙龈疾病，抑制皮肤氧化损伤，抑制依赖于第一过渡系列元素的金属酶的酶促作用，以及抑制再灌注损伤。