N,N',N'-Tris(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N',N'-Tris(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane
• 英文别名: 1-[4,7-Bis(2-hydroxy-2-methylpropyl)-1,4,7-triazonan-1-yl]-2-methylpropan-2-ol
• 化学式: C₁₈H₃₉N₃O₃
• 分子量: 345.526
• InChiKey: IZZZKEMZDZWUDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基环氧丙烷 、 1,4,7-三氮杂环壬烷 生成 N,N',N'-Tris(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane
  参考文献：
  名称：

  Discrimination between magnesium(ii) and calcium(ii) by 1,4,7-tris(2-hydroxyalkyl)-1,4,7-triazacyclononane ligands

  摘要：

  标题配体及其可能的非对映异构体形式显示大 镁络合的选择性差异 二 和 钙 二 与平面的扭转角有关 羟基相对于大环平面的配位 氮。

  DOI：

  10.1039/a701107e

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。
• 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。
• Co-ordination chemistry and molecular mechanics study of the magnesium(II) and calcium(II) complexes of trisubstituted 1,4,7-triazacyclononane derivatives
  作者：Jurriaan Huskens、A. Dean Sherry

  DOI：10.1039/a703640j

  日期：——

  The affinities of 1,4,7-tris(2-hydroxyalkyl)-1,4,7-triazacyclononane derivatives for MgII and CaII were found to differ greatly. Whereas 1,4,7-tris(2-hydroxyethyl)- (L1), 1,4,7-tris(2-hydroxy-2-methylpropyl)- (L2) and the unsymmetrical 1,4,7-tris(2-hydroxypropyl)-1,4,7-triazacyclononane derivative L3b barely discriminated between MgII and CaII, the symmetrical isomer L3a was more than 500 times more selective for MgII than for CaII. Similar selectivity differences were observed between the diastereomers of 1,4,7-tris(2-hydroxy-2-phenylethyl)- (L4) and 1,4,7-tris(2-hydroxydodecyl)-1,4,7-triazacyclononane (L5). These selectivities were related to the structure of the magnesium complexes as shown by molecular mechanics (MMX) calculations. Only those ligands favoring the formation of a magnesium complex with a large twist angle between the planes of co-ordinating oxygens and ring nitrogens resulting in a small, tight cavity showed a large preference for MgII over CaII. The MMX calculations predicted large twist angle structures for phosphinate derivatives, and for a phosphonate monoester derivative, and these ligands were found to have a high selectivity for MgII. Similarly, the calculated preference for the smaller twist angle correctly predicted the lack of MgII/CaII selectivity for acetate and amide derivatives and for a phosphonate diester derivative. Equilibration of the complexes of the ligands in the presence of both MgII and CaII was slow, as shown for example by kd,0 = 2.1 × 10–4 s–1 for CaL3a. These dissociation rates were a factor of 100 times larger at the boundary of a two-phase (water–chloroform) system.

  发现1,4,7-三(2-羟烷基)-1,4,7-三氮杂环壬烷衍生物对MgII和CaII的亲和力差异很大。而 1,4,7-三(2-羟乙基)- (L1)、1,4,7-三(2-羟基-2-甲基丙基)-(L2) 和不对称 1,4,7-三(2 (羟丙基)-1,4,7-三氮杂环壬烷衍生物L3b几乎无法区分MgII和CaII，对称异构体L3a对MgII的选择性比对CaII的选择性高500倍以上。在 1,4,7-三(2-羟基-2-苯基乙基)-(L4) 和 1,4,7-三(2-羟基十二烷基)-1,4,7-三氮杂环壬烷的非对映异构体之间观察到类似的选择性差异（L5）。正如分子力学 (MMX) 计算所示，这些选择性与镁络合物的结构有关。只有那些有利于形成镁配合物的配体，该配合物在配位氧和环氮平面之间具有大扭转角，从而形成小而紧密的空腔，才显示出对 MgII 的优先选择超过 CaII。 MMX 计算预测了次膦酸酯衍生物和膦酸酯单酯衍生物的大扭转角结构，并且发现这些配体对 MgII 具有高选择性。类似地，计算出的对较小扭转角的偏好正确地预测了 MgII/CaII 对乙酸酯和酰胺衍生物以及膦酸酯二酯衍生物缺乏选择性。在 MgII 和 CaII 存在的情况下，配体复合物的平衡很慢，如 CaL3a 的 kd,0 = 2.1 × 10–4 s–1 所示。在两相（水-氯仿）系统的边界处，这些解离速率是原来的 100 倍。
• 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。
• Method for inhibiting bacterial or fungal growth using a polyamine derivative as complexing agent
  申请人：Chelator LLC

  公开号：EP1382332A1

  公开（公告）日：2004-01-21

  The present invention refers to a method for inhibiting bacterial or fungal growth on a surface, including a human body surface, or in a solution comprising administering to said surface or solution a complexing agent having the formula wherein said radicals and integers are defined as in the description.

  本发明涉及一种抑制细菌或真菌在表面上（包括人体表面）或溶液中生长的方法，该方法包括在所述表面或溶液中施用一种具有以下式子的络合剂 其中，所述基团和整数的定义与描述相同。