3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione | 148344-88-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione
• 英文别名: 3,6,9,12,18-Pentaazabicyclo[12.3.1]octadeca-1(18),14,16-trien-2,13-dione；3,6,9,12,18-pentazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione
• CAS: 148344-88-1
• 化学式: C₁₃H₁₉N₅O₂
• 分子量: 277.326
• InChiKey: JSXQUZBGPLGVNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  682.1±55.0 °C(Predicted)
• 密度：
  1.313 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  95.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione 在 高氯酸 、 potassium nitrate 作用下， 以 水 为溶剂， 生成 3,6,9,12,18-Pentazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione;perchloric acid
  参考文献：
  名称：

  水溶液中质子和重金属离子与吡啶氮杂ac杂的酰胺酰胺大环化合物的复杂形成

  摘要：

  这项研究涉及通过电位，1 H NMR和X射线衍射方法分析不同结构和大小的酰胺大环的质子和金属离子结合。质子化的配体以3D网络结构形式存在。配体在水溶液中与重金属离子（Cu 2 +，Cd 2 +，Pb 2 +，Zn 2+和Ni 2+）形成1：1配合物，并显示出对Cu 2+阳离子的高选择性。吡啶2,6-二氨基甲酰胺片段可为冠醚提供结构刚性，从而使该分子具有开放腔，并加快了金属络合物形成的动力学。版权所有©2015 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.3526
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione
  参考文献：
  名称：

  Synthesis, Characterization, and Preclinical Evaluation of^99mTc-Labeled Macrobicyclic and Tricyclic Chelators as Single Photon Emission Computed Tomography Tracer

  摘要：

  The novel tetraaza macrobicyclic chelator 3,6,9,15‐tetraazabicyclo[9.3.1]pentadeca‐1(15),11,13‐triene‐2,10‐dione (TBPD) and pentaaza macrotricyclic chelator 9‐oxa‐3,6,12,15,21‐pentaazatricyclo[15,3,2,1]trieicos‐1(21),17,19‐triene‐2,7,11,16‐tetradione (OPTT) were synthesized, characterized, and radiolabeled with 99mTc to produce 99mTc‐TBPD and 99mTc‐OPTT. These radiolabeled complexes were prepared with high radiolabeling yield, radiochemical purity, and good in vitro stability up to 24 h. The labeling efficiency of 99mTc‐TBPD and 99mTc‐OPTT was found 98% and 97%. In vitro serum stability of 99mTc‐TBPD was found to be 95.2%, while that of 99mTc‐OPTT 94.2% up to 24 h. Blood kinetics experiments of 99mTc‐labeled complexes showed biphasic pattern of blood clearance. About 99.57 ± 0.89% activity of 99mTc‐TBPD and 99.42 ± 0.88% activity of 9mTc‐OPTT were cleared off blood stream at 24 h postadministration. The biological half‐life of 99mTc‐TBPD was observed: t1/2(F) 1 h 5 min and t1/2(S) 12 h and biological half‐life of 99mTc‐OPTT was observed: t1/2(F) 1 h 10 min and t1/2(S) 9 h 50 min, respectively. The biodistribution studies revealed that maximum uptake of 99mTc‐TBPD was found in liver, concluded that excretory pathway is hepatobiliary, while that of 99mTc‐OPTT was renal as well as hepatobiliary. The negligible activity observed in stomach confirming the stability of radiolabeled complex in biological milieu. In vitro cytotoxicity study of TBPD and OPTT did not show any considerable antiproliferative activity against cancer cells of human cervical SW756, HeLa, and glioblastoma U‐87, U373 cell lines.

  DOI：

  10.1111/cbdd.12707

文献信息

• Manganese complexes of nitrogen-containing macrocyclic ligands effective
  申请人：G. D. Searle & Co.

  公开号：US05874421A1

  公开（公告）日：1999-02-23

  The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: ##STR1## wherein R, R', R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5, R.sub.6, R'.sub.6, R.sub.7, R'.sub.7, R.sub.8, R'.sub.8, R.sub.9, and R'.sub.9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

  本发明涉及超氧化物歧化酶（SOD）的低分子量模拟物，其化学式为：##STR1## 其中R、R'、R₁、R'₁、R₂、R'₂、R₃、R'₃、R₄、R'₄、R₅、R'₅、R₆、R'₆、R₇、R'₇、R₈、R'₈、R₉和R'₉以及X、Y、Z和n的定义如本文所述，可用作治疗炎症性疾病状态和紊乱、缺血/再灌注损伤、中风、动脉粥样硬化、高血压和所有其他由氧化剂引起的组织损伤或损伤的条件的治疗剂。
• Iron(II) Complexes with Amide-Containing Macrocycles as Non-Heme Porphyrin Analogues
  作者：Ivan V. Korendovych、Olga P. Kryatova、William M. Reiff、Elena V. Rybak-Akimova

  DOI：10.1021/ic0701209

  日期：2007.5.1

  same conditions. The reaction is first-order in both iron(II) complex and dioxygen, and no intermediate is spectroscopically observed. Similar behavior was observed for the monodeprotonated complex Fe(HpydioneN5)(Cl). The presence of an accessible proton either from the solvent (reactions in methanol) or from the complex itself (in Fe(HpydioneN5)(Cl)) proves sufficient to alter the oxygenation pathway

  大环十五碳烯配体3,6,9,12,18-五氮杂双环[12.3.1] octadeca-1（18），14,16-三烯-2,13-二酮（H2pydioneN5）和16-氯的铁（II）配合物合成并充分表征了-3,6,9,12,18-五氮杂双环[12.3.1] octadeca-1（18），14,16-三烯-2,13-二烯（H2pyCldioneN5）。均分离了具有一个或两个H2pydione的去质子化酰胺基的配合物。在前一种情况下，金属离子具有扭曲的八面体配位球；在后一种情况下，复合体采用五边形-双锥体的几何形状。NMR实验表明，配体的质子化状态保留在二甲基亚砜（DMSO）溶液中。即使在低温下，配合物也保持高自旋状态。铁（II）配合物氧合的详细动力学研究表明，配合物的去质子化状态对与双氧的反应性具有深远的影响。铁（II）的双质子化复合物Fe（pydioneN5）在质子惰性溶剂中的氧化过程类似于铁
• Potentiometric studies of complex formation of amidopyridine macrocycles bearing pendant arms with proton and heavy metal ions in aqueous solution
  作者：Yu. V. Fedorov、O.A. Fedorova、S.N. Kalmykov、M.S. Oshchepkov、Yu. V. Nelubina、D.E. Arkhipov、B.V. Egorova、A.D. Zubenko

  DOI：10.1016/j.poly.2016.12.037

  日期：2017.3

  values for the Cu2+, Ni2+ and Pb2+ complexes of ligand containing three carboxylic arms are exceptionally high. Single crystal structures of a few complexes with Cu2+ and Pb2+ were determined. In all complexes, the metal centre exhibit a strong coordination with amine N-atoms and arm’s ligand groups. The rigid structure of pyridine-2,6-dicarbamide fragment and an open macrocyclic cavity provide a possibility

  摘要合成了一种新型的含吡啶或羧基侧链的吡啶-氮杂row杂醚酰胺大环。通过电位法测定了化合物的质子化常数及其与多种金属离子（Ag +，Cu2 +，Zn2 +，Cd2 +，Ni2 +，Pb2 +，Y3 +，Eu3 +，Lu3 +）的配合物的稳定性常数。发现形成了大环与阳离子的不同络合物，包括HML，ML和ML（OH）n。配合物稳定性的增加提供了吡啶-氮杂row杂醚酰胺大环中羧基取代基的存在。包含三个羧基臂的配体的Cu2 +，Ni2 +和Pb2 +配合物的值非常高。确定了一些与Cu2 +和Pb2 +形成的配合物的单晶结构。在所有建筑群中 金属中心与胺的N原子和臂的配体基团具有很强的配位作用。吡啶-2,6-二氨基甲酰胺片段的刚性结构和开放的大环腔为复合物形成的快速动力学提供了可能。
• A New High-Spin Iron(III) Complex with a Pentadentate Macrocyclic Amidopyridine Ligand:  A Change from Slow Single-Ion Paramagnetic Relaxation to Long-Range Antiferromagnetic Order in a Hydrogen-Bonded Network
  作者：Ivan V. Korendovych、Richard J. Staples、William M. Reiff、Elena V. Rybak-Akimova

  DOI：10.1021/ic0351601

  日期：2004.6.28

  A new, stable iron(III) complex with a pentadentate amide-containing macrocyclic ligand was prepared and fully characterized. The complex adopted a pentagonal-bipyramidal geometry, where an equatorial plane is occupied by the pyridine nitrogen, two deprotonated amide nitrogens, and two secondary amines from the macrocycle, and two axial positions are available for monodentate ligand (chloride anion

  制备了具有五齿含酰胺大环配体的新型稳定铁（III）配合物，并对其进行了全面表征。该络合物采用五边形-双锥体的几何构型，其中一个大环上的吡啶氮，两个去质子化的酰胺氮和两个仲胺占据了一个赤道平面，并且两个轴向位置可用于单齿配体（氯离子或溶剂分子）的配位。 。刚性的平面铁酰胺结构单元通过氢键系统在三维网络中相连，Fe-Fe间隔最短为8.02A。强供电子，带负电荷的去质子化酰胺基团的配位导致铁的高氧化态的预期稳定作用（Fe（III）L / Fe（II）L对的氧化还原电势，-0.57 V对SCE）。与大多数具有多齿酰胺配体的铁配合物相反，本文描述的大环配合物的五边形-双锥体几何结构提供了中心金属离子的高自旋构型（室温磁矩为5.84microβ） ）。变温铁57 Mossbauer光谱和交，直流磁化研究表明，顺磁弛豫缓慢，并且在T <约3.2 K时与长距离反铁磁阶交叉。
• A novel method for the synthesis of acyclic ligands with combined chelating groups
  作者：Anna A. Shchukina、Anastasia D. Zubenko、Olga A. Fedorova

  DOI：10.1016/j.tet.2023.133773

  日期：2024.1

  developed in this work provides a simple route to the acyclic versatile ligands with combined chelating groups. The approach involves three-step synthesis: the preparation of amide macrocyclic derivatives containing one type of chelating substituents, hydrolysis of macrocyclic compounds giving the acyclic derivatives with unsubstituted terminal amino groups and final modification of terminal amines by another

  这项工作中开发的合成方法为具有组合螯合基团的无环多功能配体提供了一条简单的途径。该方法涉及三步合成：制备含有一种类型的螯合取代基的酰胺大环衍生物，水解大环化合物得到具有未取代的末端氨基的无环衍生物，最后用另一种类型的螯合取代基对末端胺进行修饰。所得络合物结合了不同性质的螯合取代基，可用于进一步研究医用金属阳离子在放射性药物中的应用。