1,4,7-tris(carbamoylmethyl)-1,4,7-triazacyclononane | 180297-76-1

• 物质功能分类: 生物 - 蛋白&多肽
• 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-tris(carbamoylmethyl)-1,4,7-triazacyclononane
• 英文别名: Notam；2-[4,7-bis(2-amino-2-oxoethyl)-1,4,7-triazonan-1-yl]acetamide
• CAS: 180297-76-1
• 化学式: C₁₂H₂₄N₆O₃
• 分子量: 300.361
• InChiKey: ALRKEASEQOCKTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  630.2±55.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,7-tris(carbamoylmethyl)-1,4,7-triazacyclononane 以 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  The NiCEST Approach: Nickel(II) ParaCEST MRI Contrast Agents

  摘要：

  Paramagnetic Ni(II) complexes are shown here to form paraCEST MRI contrast agents (paraCEST = paramagnetic: chemical exchange saturation transfer; NICEST = Ni(II) based CEST agents). Three azamacro-cycles with amide pendent groups bind Ni(II) to form stable NiCEST contrast agents including 1,4,7-tris-(carbamoylmethyl)-1,4,7-triazacyclononane. (L1), 1,4,8,11-tetrakis(carbamoylmethyl)-1,4,8,11-tetraazacyclo-tetradecane (L2), and 7,13-bis(carbamoylmethyl)-1,4,10-trioxa-7,13-diazacyclopentadecane (L3). [Ni(L3)](2+), [Ni(L1)](2+), and [Ni(L2)](2+) have CEST peaks attributed to amide protons that are shifted 72, 76, and 76 ppm from the bulk water resonance, respectively. Both CEST MR images and CEST spectroscopy show that [Ni(L3)](2+) has the largest CEST effect in 100 mM NaCl, 20 mM HEPES pH 7.4 at 37 degrees C. This larger CEST effect is attributed to the sharper proton resonances of the complex which arise from a rigid structure and low relaxivity.

  DOI：

  10.1021/ja307909x
• 作为产物：
  描述：

  在 disodium hydrogenphosphate 、 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt 、 potassium carbonate 、 sodium chloride 作用下， 生成 1,4,7-tris(carbamoylmethyl)-1,4,7-triazacyclononane
  参考文献：
  名称：

  The NiCEST Approach: Nickel(II) ParaCEST MRI Contrast Agents

  摘要：

  Paramagnetic Ni(II) complexes are shown here to form paraCEST MRI contrast agents (paraCEST = paramagnetic: chemical exchange saturation transfer; NICEST = Ni(II) based CEST agents). Three azamacro-cycles with amide pendent groups bind Ni(II) to form stable NiCEST contrast agents including 1,4,7-tris-(carbamoylmethyl)-1,4,7-triazacyclononane. (L1), 1,4,8,11-tetrakis(carbamoylmethyl)-1,4,8,11-tetraazacyclo-tetradecane (L2), and 7,13-bis(carbamoylmethyl)-1,4,10-trioxa-7,13-diazacyclopentadecane (L3). [Ni(L3)](2+), [Ni(L1)](2+), and [Ni(L2)](2+) have CEST peaks attributed to amide protons that are shifted 72, 76, and 76 ppm from the bulk water resonance, respectively. Both CEST MR images and CEST spectroscopy show that [Ni(L3)](2+) has the largest CEST effect in 100 mM NaCl, 20 mM HEPES pH 7.4 at 37 degrees C. This larger CEST effect is attributed to the sharper proton resonances of the complex which arise from a rigid structure and low relaxivity.

  DOI：

  10.1021/ja307909x

文献信息

• [EN] MACROCYCLES, COBALT AND IRON COMPLEXES OF SAME, AND METHODS OF MAKING AND USING SAME<br/>[FR] MACROCYCLES, COMPLEXES DE COBALT ET DE FER DE CEUX-CI, ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION CORRESPONDANTS
  申请人：RES FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK UNIVERSITY AT BUFFALO

  公开号：WO2015038943A1

  公开（公告）日：2015-03-19

  Provided are macrocyclic compounds and iron or cobalt coordinated macrocyclic compounds. The compounds can be used as MRI contrast agents. Certain compounds are redox active and can be used to assess the biological redox status of a sample.

  提供的是大环化合物和铁或钴配位的大环化合物。这些化合物可以用作磁共振成像对比剂。某些化合物具有氧化还原活性，可用于评估样品的生物氧化还原状态。
• 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。
• Nickel(II) Complexes as Paramagnetic Shift and paraCEST Agents
  作者：Samira M. Abozeid、Eric M. Snyder、Alejandra P. Lopez、Charles M. Steuerwald、Eric Sylvester、Kamal M. Ibrahim、Rania R. Zaky、Hamed M. Abou‐El‐Nadar、Janet R. Morrow

  DOI：10.1002/ejic.201800021

  日期：2018.5.15

  2′‐(7‐benzyl‐1,4,7‐triazonane‐1,4‐diyl) diacetamide (L5). Solution magnetic moments are consistent with paramagnetic NiII complexes. The complexes are characterized by pH‐potentiometric titrations to determine the pKa values of the bound amide or alcohol pendents or water ligand. Variable temperature 17O NMR studies are consistent with a water ligand in [Ni(L5)]2+ with an exchange rate constant of 4 × 104 s–1

  研究了五个Ni II大环配合物作为水质子转移剂和paraCEST剂（paraCEST =顺磁性化学交换饱和转移），用于MRI应用。五个大环具有酰胺和/或醇侧基，具有四氮杂或三氮杂大环，包括1,1'，1''-（1,4,7-三氮杂烷-1,4,7-三基）三（丙烷-2- ol）（L1），1,1′，1′′，1′′′-（1,4,7,10-四氮杂环十二烷-1,4,7,10-tetra）四（丙烷-2-醇）（L2），1,1'，1''，1'''-（1,4,8,11-四氮杂环十四烷-1,4,8,11-四基）四（丙烷-2-醇）（L3）， 2,2'，2''-（1,4,7-三唑烷-1,4,7-三基）三乙酰胺（L4）或2,2'-（7-苄基-1,4,7-三唑烷- 1,4-二基）二乙酰胺（L5）。溶液磁矩与顺磁性Ni II络合物一致。通过pH电位滴定法表征复合物，以确定结合的酰胺或醇类或水配体的p K a值。可变温度17 O
• Tb(III)配合物及其制备方法和在检测杀螟腈 中的应用
  申请人：陕西师范大学

  公开号：CN104892533B

  公开（公告）日：2017-03-29

  本发明公开了一种Tb(III)配合物及其制备方法和在检测杀螟腈中的应用。该配合物的结构式为其是以1,4,7‑三氮杂环壬烷衍生物为配体，与Tb(III)配合而成的，制备方法极其简单，反应条件温和。本发明Tb(III)配合物具有荧光寿命长、斯托克斯位移大和配位不饱和等特点，可以和中性分子杀螟腈有效配位，并且Tb(III)的5D4能级与杀螟腈的T1能级高度匹配，确保二者之间可发生有效能量转移而大幅敏化Tb(III)配合物的荧光。因此，该配合物对杀螟腈具有较强的选择性，能够实现对杀螟腈的高选择性、高灵敏度传感识别，并且操作过程简单便捷，为杀螟腈的高效检测提供了一种便捷、快速低耗的新方法。
• Synthesis and characterization of the yttrium(III) and lutetium(III) complexes of 1,4,7-tris(carbamoylmethyl)-1,4,7-triazacyclononane (TCMT). Crystal structure of [Y(TCMT)(CF3SO3)2(H2O)](CF3SO3)
  作者：Shahid Amin、Christian Marks、Laurence M. Toomey、Melvyn Rowen Churchill、Janet R. Morrow

  DOI：10.1016/0020-1693(96)05056-6

  日期：1996.5

  The 1,4,7-tris(carbamoylmethyl)-1,4,7-triazacyclononane (TCMT) ligand and its complexes with yttrium(III) and lutetium(III) have been prepared. [Y(TCMT)(CF3SO3)2(H2O)](CF3SO3) crystallizes in the centrosymmetric triclinic space group P1 (No. 2) with a = 10.3660(14), b = 11.7663(15), c = 13.3008(20) A, α = 72.079(10), β = 81.684(12), γ = 78.401(11)°, V = 1506.1(4) and Z = 2. The structure was refined

  制备了1,4,7-三（氨基甲酰基甲基）-1,4,7-三氮杂环壬烷（TCMT）配体及其与钇（III）和（III）的配合物。[Y（TCMT）（CF3SO3）2（H2O）]（CF3SO3）在中心对称三斜空间群P1（No. 2）中结晶，其中a = 10.3660（14），b = 11.7663（15），c = 13.3008（20） A，α= 72.079（10），β= 81.684（12），γ= 78.401（11）°，V = 1506.1（4）和Z =2。对于1758个反射，该结构细化为R = 5.64％。佛| >6σ（| Fo |）。非配位的钇（III）离子具有一个键合的水分子，两个键合的三氟甲磺酸根离子和一个六齿TCMT配体。配位几何形状可以描述为3：5：1排列，其中C6N3骨架占据'3'位置，H2O占据独特的'1'位置，或者可替代地描述为带帽的方形棱镜或扭曲的三棱柱形棱镜。[Ln（TCMT）]