(1,4-dibenzyl-6-nitro-1,4-diazepan-6-yl)methanol | 1173766-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1,4-dibenzyl-6-nitro-1,4-diazepan-6-yl)methanol
• 英文别名: 1,4-dibenzyl-6-hydroxymethyl-6-nitroperhydro-1,4-diazepine
• CAS: 1173766-86-3
• 化学式: C₂₀H₂₅N₃O₃
• 分子量: 355.437
• InChiKey: OCPJEQPMKCZIHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1,4-dibenzyl-6-nitro-1,4-diazepan-6-yl)methanol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以97%的产率得到potassium 1,4-dibenzylperhydro-1,4-diazepine-6-carbonitrate
  参考文献：
  名称：

  通过新型串联逆向亨利和曼尼希/迈克尔反应合成6-取代的6-Nitroperhydro-1,4-二氮杂pine

  摘要：

  N，N'-二苄基-6-羟甲基-6-硝基过氢-1,4-二氮杂via通过逆亨利反应转化为亚硝酸盐，然后通过迈克尔反应与几种丙烯酸衍生物或曼尼希反应与不同的胺反应，从而导致6-取代的6-硝基过氢-1,4-二氮杂s。的串联回亨利/曼尼希反应也进行了，使用苄胺作为碱，溶剂和试剂在同一时间。还成功实现了硝基的选择性加氢和完全氢解。

  DOI：

  10.1021/ol203101s
• 作为产物：
  描述：

  聚合甲醛 、 2-硝基乙醇 、 N,N'-二苄基乙二胺二醋酸 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 以99.5%的产率得到(1,4-dibenzyl-6-nitro-1,4-diazepan-6-yl)methanol
  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

• [Gd(AAZTA)] ⁻ Derivatives with <i>n</i> ‐Alkyl Acid Side Chains Show Improved Properties for Their Application as MRI Contrast Agents**
  作者：Flávio Vinicius Crizóstomo Kock、Attila Forgács、Nicol Guidolin、Rachele Stefania、Adrienn Vágner、Eliana Gianolio、Silvio Aime、Zsolt Baranyai

  DOI：10.1002/chem.202004479

  日期：2021.1.21

  dro‐1,4‐diazepine tetra acetic acid) derivatives functionalized with short (C2 and C4) n‐alkyl acid functions are reported. The carboxylate functionality is the site for further conjugations for the design of more specific contrast agents (CAs). Interestingly, it has been found that the synthesized complexes display enhanced properties for use as MRI contrast agents on their own. The stability constants

  在这里，合成和广泛表征的两个短（C 2和C 4）n功能化的新型Gd（AAZTA）（AAZTA = 6-氨基-6-甲基过氢-1,4-二氮杂四乙酸）衍生物报告了烷基酸功能。羧酸盐官能团是设计更多特异性造影剂（CA）的其他方法。有趣的是，已经发现合成的复合物单独显示出增强的性能以用作MRI造影剂。通过电位滴定法和UV / Vis分光光度法测定的稳定性常数略高于母体Gd（AAZTA）络合物的报道值。相对于母体络合物中的甲基所提供的酰基取代基而言，酰基取代基的更大σ电子捐赠可能解释了这一现象。至于动力学稳定性，内源性离子（例如Cu 2+）的金属转移实验表明，Gd 3+这些Gd（AAZTA）衍生物中存在的离子在接近生理条件的情况下，在25°C下对这些离子进行化学交换的敏感性较小。具有Eu III和Yb III的配合物的1 H NMR光谱显示了一组信号，这些信号与每个配体上存在的亚甲基质子的数量一致。共
• Radiolabeled Dibenzodiazepinone-Type Antagonists Give Evidence of Dualsteric Binding at the M₂ Muscarinic Acetylcholine Receptor
  作者：Andrea Pegoli、Xueke She、David Wifling、Harald Hübner、Günther Bernhardt、Peter Gmeiner、Max Keller

  DOI：10.1021/acs.jmedchem.6b01892

  日期：2017.4.27

  monomeric and the dimeric compound bind to the orthosteric binding site (apparent Kd: 0.87 and 0.31 nM, respectively). Various binding studies with [3H]19 and [3H]33 at the M2R, for instance, saturation binding experiments in the presence of the allosteric MR modulators W84 (8) or LY2119620 (9) (Schild-like analysis) suggested a competitive mechanism between the allosteric modulator and the dibenzodiazepinone

  针对具有改进的亚型选择性的配体的双空间配体方法已经越来越多地应用于毒蕈碱受体（MRs）。在本文中，我们介绍了M 2 R亚型放射性标记的二苯并二氮杂pin酮类拮抗剂（[ 3 H] UNSW-MK259，[ 3 H] 19）及其同型二聚体类似物[ 3 H] UR-AP060（ [ 3 H] 33）。使用正构拮抗剂阿托品对M 2 R的饱和结合研究来确定非特异性结合，证明单体和二聚体化合物与正构结合位点结合（表观K d：分别为0.87和0.31 nM）。用[ 3 H] 19和[ 3 H] 33在M 2 R进行的各种结合研究，例如，在变构MR调节剂W84（8）或LY2119620（9）存在下的饱和结合实验（Schild-like分析）提出了变构调节剂和二苯并二氮杂吡啶酮衍生物之间的竞争机制，因此是19和33的双空间结合模式。这与使用19和33进行的M 2 R MD仿真（≥2μs）的结果一致。
• BIFUNCTIONAL CHELATING AGENTS BASED ON THE 1,4-DIAZEPINE SCAFFOLD (DAZA) FOR NON-INVASIVE MOLECULAR IMAGING
  申请人：JOHANNES GUTENBERG-UNIVERSITÄT MAINZ

  公开号：US20160136309A1

  公开（公告）日：2016-05-19

  A compound fur radio metal complexation includes a chelator and one or more biological targeting vectors TV conjugated to said chelator, wherein the chelator has structure (A) or (B)or (C). based on 1,4-diazepine with groups R 1 , R 2 , R 3 , R 4 , X 1 , X 2 , X 3 . The compound is particularly suited for complexation of radio-isotopic metals, such as 66 Ga(III), 67 Ga(III) and 68 Ga(III).
• [EN] BIFUNCTIONAL CHELATING AGENTS BASED ON THE 1,4-DIAZEPINE SCAFFOLD (DAZA) FOR NON-INVASIVE MOLECULAR IMAGING<br/>[FR] AGENTS CHÉLATEURS BIFONCTIONNELS À BASE DE L'ÉCHAFAUDAGE 1,4-DIAZÉPINE (DAZA) POUR L'IMAGERIE MOLÉCULAIRE NON INVASIVE
  申请人：JOHANNES GUTENBERG UNIVERSITÄT MAINZ

  公开号：WO2014198478A2

  公开（公告）日：2014-12-18

  A compound for radio metal complexation comprises a chelator and one or more biological targeting vectors TV conjugated to said chelator, wherein the chelator has structure (A) or (B) or (C), based on 1,4-diazepine with groups R1; R2, R3, R4, X1, X2, X3. The compound is particularly suited for complexation of radio-isotopic metals, such as 66Ga(III), 67Ga(III) and 68Ga(III).
• Fast and easy access to efficient bifunctional chelators for MRI applications
  作者：Giuseppe Gugliotta、Mauro Botta、Giovanni Battista Giovenzana、Lorenzo Tei

  DOI：10.1016/j.bmcl.2009.05.024

  日期：2009.7

  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.