1,4-bis(t-butoxycarbonylmethyl)-6-[bis(t-butoxycarbonylmethyl)]amino-6-hydroxymethylperhydro-1,4-diazepine | 1173766-95-4

• 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-bis(t-butoxycarbonylmethyl)-6-[bis(t-butoxycarbonylmethyl)]amino-6-hydroxymethylperhydro-1,4-diazepine
• CAS: 1173766-95-4
• 化学式: C₃₀H₅₅N₃O₉
• 分子量: 601.781
• InChiKey: BEXNSFVWRUBWJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  135.15
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(t-butoxycarbonylmethyl)-6-[bis(t-butoxycarbonylmethyl)]amino-6-hydroxymethylperhydro-1,4-diazepine 在 potassium carbonate 作用下， 生成 1,8,11-tris(t-butoxycarbonylmethyl)-1,8,11-triaza-4-oxa-3-oxospiro[5.6]dodecane
  参考文献：
  名称：

  Fast and easy access to efficient bifunctional chelators for MRI applications

  摘要：

  Novel bifunctional agents based on the AAZTA (6-amino-6-methylperhydro-1,4-diazepinetetraacetic acid) structure with hydroxyl, carboxyl and chloro functional groups were prepared. The Gd-III complexes show optimal magnetic properties making them very good candidates for conjugation to biomolecules for molecular imaging applications. An example of conjugation to a bile acid derivative is also reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.024
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 6-amino-6-hydroxymethylperhydro-1,4-diazepine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以53%的产率得到1,4-bis(t-butoxycarbonylmethyl)-6-[bis(t-butoxycarbonylmethyl)]amino-6-hydroxymethylperhydro-1,4-diazepine
  参考文献：
  名称：

  Fast and easy access to efficient bifunctional chelators for MRI applications

  摘要：

  Novel bifunctional agents based on the AAZTA (6-amino-6-methylperhydro-1,4-diazepinetetraacetic acid) structure with hydroxyl, carboxyl and chloro functional groups were prepared. The Gd-III complexes show optimal magnetic properties making them very good candidates for conjugation to biomolecules for molecular imaging applications. An example of conjugation to a bile acid derivative is also reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.024

文献信息

• Rigid and Compact Binuclear Bis‐hydrated Gd‐complexes as High Relaxivity MRI Agents
  作者：Loredana Leone、Luca Guarnieri、Jonathan Martinelli、Massimo Sisti、Andrea Penoni、Mauro Botta、Lorenzo Tei

  DOI：10.1002/chem.202101701

  日期：2021.8.16

  Gd-complexes. Thus, the 1H relaxometric study on [Gd2PCTA2(H2O)4] and on [Gd2AAZTA2(H2O)4]2− highlighted the remarkable rigidity and compactness of the two binuclear complexes, which results in molar relaxivities (per Gd), at 1.5 T and 298 K of ca. 12–12.6 mM−1 s−1 with an increase of ca. 80 % at 1.5 T and 298 K (+70 % at 310 K) with respect to the corresponding mononuclear complexes.

  12 元吡啶基聚氨基羧酸盐大环配体 PCTA 的第一个双核 Gd 配合物是通过两种不同的合成程序通过吡啶单元的 C-C 连接合成的。还合成了二聚 AAZTA 配体，目的是比较松弛测量结果或两种双位 Gd 复合物。因此，[Gd 2 PCTA 2 (H 2 O) 4 ] 和 [Gd 2 AAZTA 2 (H 2 O) 4 ] 2−的1 H 弛豫研究突出了两种双核配合物的显着刚性和致密性，结果摩尔弛豫率（每 Gd），在 1.5 T 和 298 K 的约。12–12.6 毫米-1  s -1增加约。相对于相应的单核复合物，在 1.5 T 和 298 K 时为 80%（在 310 K 时为 +70%）。
• Orthogonal synthesis of a heterodimeric ligand for the development of the GdIII–GaIII ditopic complex as a potential pH-sensitive MRI/PET probe
  作者：Nikolay Vologdin、Gabriele A. Rolla、Mauro Botta、Lorenzo Tei

  DOI：10.1039/c2ob27200h

  日期：——

  A heterodimeric polyaminocarboxylate ligand based on a DO3A-sulfonamide linked to AAZTA (6-amino-6-methylperhydro-1,4-diazepinetetracarboxylic acid) was synthesised via an orthogonal pathway in order to differentiate the two chelating cages and allow the formation of a GdIII–GaIII heteroditopic complex. The goal is to create a smart MRI/PET probe with pH dependent relaxivity and with the bimodal imaging approach that enables direct quantification of the stimulus, in this case pH. A 1H NMR relaxometric study of the Gd–Ga heteroditopic complex addressed the pH modulation of the relaxivity and thus its possible use as an MRI pH sensitive probe.

  我们通过正交途径合成了一种基于 DO3A 磺酰胺与 AAZTA（6-氨基-6-甲基全氢-1,4-二氮杂环庚烷四羧酸）的异二聚体多氨基羧酸配体，以区分两种螯合笼，并形成 GdIIIâGaIII 异二聚体复合物。我们的目标是研制出一种智能 MRI/PET 探针，它具有与 pH 值相关的弛豫性，并采用双模成像方法，能够直接量化刺激因素（在本例中为 pH 值）。对 GdâGa 异二价复合物进行的 1H NMR 驰豫度研究解决了驰豫度的 pH 值调制问题，因此可以将其用作 MRI pH 值敏感探针。
• AAZTA-based bifunctional chelating agents for the synthesis of multimeric/dendrimeric MRI contrast agents
  作者：Giuseppe Gugliotta、Mauro Botta、Lorenzo Tei

  DOI：10.1039/c0ob00096e

  日期：——

  Monomeric and dimeric bifunctional chelates based on the AAZTA (6-amino-6-methylperhydro-1,4-diazepinetetraacetic acid) platform bearing arylamino and isothiocyanate groups for conjugation to biomolecules were synthesised. Both systems were used for the preparation of high relaxivity dendrimeric (PAMAM G1) and multimeric octa-GdIII complexes. These systems show enhanced relaxometric properties attributed to the presence of two coordinated, fast exchanging, water molecules (q = 2) on each metal ion and to a rather rigid and compact molecular structure.

  我们合成了基于 AAZTA（6-氨基-6-甲基全氢-1,4-二氮杂环四乙酸）平台的单体和二聚体双功能螯合物，该平台带有用于与生物大分子共轭的芳基氨基和异硫氰酸基。这两种体系均用于制备高松弛性树枝状（PAMAM G1）和多聚八-GdIII 复合物。由于每个金属离子上都有两个配位的、快速交换的水分子（q = 2），而且分子结构相当坚固紧凑，因此这些体系显示出更强的弛豫特性。