N,N′-(pyridine-2,6-diylbis(methylene))dianiline | 1248447-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N′-(pyridine-2,6-diylbis(methylene))dianiline
• 英文别名: 2,6-bis(anilinomethyl)pyridine；N,N'-(pyridine-2,6-diylbis(methylene))dianiline；N-[[6-(anilinomethyl)pyridin-2-yl]methyl]aniline
• CAS: 1248447-17-7
• 化学式: C₁₉H₁₉N₃
• 分子量: 289.38
• InChiKey: QCMVVRQHKNADIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N′-(pyridine-2,6-diylbis(methylene))dianiline 在 2,6-二甲基吡啶 、 dipotassium hydrogenphosphate 、 三氟甲磺酸三甲基硅酯 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 diethyl 2,2′-((pyridine-2,6-diylbis(methylene))bis((4-((4,5-dimethoxy-2-nitrophenyl)(hydroxy)methyl)phenyl)azanediyl))diacetate
  参考文献：
  名称：

  Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺Photocages Using Multiple Nitrobenzyl Groups

  摘要：

  Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn2+ chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal bound aniline ligands, which decreases the Zn2+ affinity 190 fold The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14 fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,Ni-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn2+-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn2+ complexes, and photolysis of two photolabile groups increases the Zn2+ affinity changes to 480 fold The Zn2+, Cu2+, and Cd2+ binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn2+-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.

  DOI：

  10.1021/ic400465g
• 作为产物：
  描述：

  2,6-bis[(phenylamino)methylene]pyridine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 N,N′-(pyridine-2,6-diylbis(methylene))dianiline
  参考文献：
  名称：

  Synthesis of pyridine derivatives as potential antagonists of chemokine receptor type 4

  摘要：

  一系列吡啶衍生物被合成为潜在的趋化因子受体4的抑制剂。这种趋化因子受体已与各种疾病途径相关联，包括HIV-1增殖、自身免疫疾病、炎症性疾病和癌症转移。这些化合物通过亲和结合测定和抑制细胞侵袭能力的测定进行了活性测试。已确定两种命中化合物（2b和2j）进行进一步评估，这些化合物通过细胞侵袭至少抑制50%，并在亲和结合测定中的有效浓度小于100 nM。合成化合物的结构已通过光谱数据确认。

  DOI：

  10.1515/hc-2014-0041

文献信息

• Reusable Co-nanoparticles for general and selective <i>N</i>-alkylation of amines and ammonia with alcohols
  作者：Zhuang Ma、Bei Zhou、Xinmin Li、Ravishankar G. Kadam、Manoj B. Gawande、Martin Petr、Radek Zbořil、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1039/d1sc05913k

  日期：——

  A general cobalt-catalyzed N-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generated in situ by mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based

  报道了一种通用的钴催化胺与醇的N-烷基化反应，利用氢方法制备不同种类的胺。这种转化的最佳催化剂是通过热解特定的模板材料来制备的，该模板材料是通过混合钴盐、氮配体和胶态二氧化硅原位生成的，然后去除二氧化硅。应用这种新型Co纳米粒子基材料，>100伯胺、仲胺和叔胺（包括N-甲胺）和选定的药物分子可以从廉价且容易获得的醇和胺或氨开始方便地制备。
• Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst
  作者：Amreen K. Bains、Abhishek Kundu、Sudha Yadav、Debashis Adhikari

  DOI：10.1021/acscatal.9b02977

  日期：2019.10.4

  bench-stable azo-phenolate ligand-coordinated nickel catalyst which can efficiently execute N-alkylation of a variety of anilines by alcohol. We demonstrate that the redox-active azo ligand can store hydrogen generated during alcohol oxidation and redelivers the same to an in-situ-generated imine bond to result in N-alkylation of amines. The reaction has wide scope, and a large array of alcohols can directly

  我们在这里报道了一种定义明确且稳定的偶氮酚盐配体配位的镍催化剂，该催化剂可以通过醇有效地进行多种苯胺的N-烷基化。我们证明，氧化还原活性偶氮配体可以存储在醇氧化过程中产生的氢，并将其重新转移到原位产生的亚胺键上，从而导致胺的N-烷基化。该反应的范围很广，并且大量的醇可以直接偶联到各种苯胺上。包括氘标记到基质上的机理研究建立了从醇中借用氢的方法，并指出了存在于配体主链上的氧化还原活性偶氮部分的关键作用。用自由基猝灭剂和更高的k H / k分离捕获形式的酮基中间体醇氧化步骤的D建议将氢原子转移（HAT）完全转移到还原的偶氮主链上，以铺平醇氧化，这与常规的金属-配体双功能机理相反。该实施例清楚地表明，廉价的贱金属催化剂可以在氧化还原活性配体主链的帮助下完成重要的偶联反应。
• Solvent-Free N-Alkylation and Dehydrogenative Coupling Catalyzed by a Highly Active Pincer-Nickel Complex
  作者：Vinay Arora、Moumita Dutta、Kanu Das、Babulal Das、Hemant Kumar Srivastava、Akshai Kumar

  DOI：10.1021/acs.organomet.0c00233

  日期：2020.6.8

  The synthesis and characterization of a pincer-nickel complex of the type (iPr2NNN)NiCl2(CH3CN) is reported here. We have demonstrated the utility of this pincer-nickel complex (0.02 and 0.002 mol %) for the catalytic N-alkylation of amines using various alcohols. Under solvent-free conditions, while the highest yield (ca. 90%) was obtained for the alkylation of 2-aminopyridine with naphthyl-1-methanol

  （i Pr2 NNN）NiCl 2（CH 3型）的钳镍配合物的合成与表征CN）在这里报告。我们已经证明了这种夹钳-镍配合物（0.02和0.002mol％）对于使用各种醇的胺的催化N-烷基化的实用性。在无溶剂条件下，用2-甲基萘-1-甲醇烷基化2-氨基吡啶的收率最高（约90％），而用4-甲基烷基磺酸2-氨基吡啶的烷基化收率高（34000 TONs）。甲氧基苄醇。为了证明这些系统的合成效用，已探查了具有较高负载的钳制镍催化剂（4摩尔％）的代表性底物的高产率反应（高达98％）。DFT研究表明，尽管消除β-氢化物是酒精脱氢的RDS，N-烷基化产物既可以通过加氢速率决定σ键的复分解反应进行氢化，也可以通过具有亚胺插入作为RDS的醇解反应形成。通过HRMS（ESI）分析已观察到所有相应的静止状态。标记实验还与DFT研究相辅相成，并显示了RDS中的苄基C–H键与DFT研究有关的证据。k CHH / k CHD值约为2
• Synthesis and evaluation of 2,5 and 2,6 pyridine-based CXCR4 inhibitors
  作者：Theresa Gaines、Davita Camp、Renren Bai、Zhongxing Liang、Younghyoun Yoon、Hyunsuk Shim、Suazette Reid Mooring

  DOI：10.1016/j.bmc.2016.08.018

  日期：2016.11

  Targeting the interaction between G-Protein Coupled Receptor, CXCR4, and its natural ligand CXCL12 is a leading strategy to mitigate cancer metastasis and reduce inflammation. Several pyridine-based compounds modeled after known small molecule CXCR4 antagonists, AMD3100 and WZ811, were synthesized. Nine hit compounds were identified. These compounds showed lower binding concentrations than AMD3100

  靶向G蛋白偶联受体CXCR4及其天然配体CXCL12之间的相互作用是减轻癌症转移和减少炎症的领先策略。合成了以已知的小分子CXCR4拮抗剂AMD3100和WZ811为模型的几种基于吡啶的化合物。鉴定出九种命中化合物。这些化合物的结合浓度低于AMD3100（1000 nM），九种化合物中的六种有效浓度（EC）小于或等于WZ811（10 nM）。其中两种命中化合物（2g和2w）以比AMD3100（62％）更高的速率抑制转移细胞的侵袭。化合物2g和2w在足爪水肿测试中，也可将炎症抑制在与WZ811相同的范围内，使炎症减少40％。这些初步结果是新型的基于吡啶的CXCR4拮抗剂的有前途的基础。
• Synthesis of pyridine derivatives as potential antagonists of chemokine receptor type 4
  作者：Suazette Reid Mooring、Theresa Gaines、Zhongxing Liang、Hyunsuk Shim

  DOI：10.1515/hc-2014-0041

  日期：2014.6.1

  A series of pyridine derivatives were synthesized as potential inhibitors of chemokine receptor type 4. This chemokine receptor has been linked to various disease pathways including HIV-1 proliferation, autoimmune disorders, inflammatory diseases, and cancer metastasis. The compounds were tested for activity using an affinity binding assay and an assay that tests the ability to inhibit cell invasion. Two hit compounds (2b and 2j) have been identified for further evaluation that inhibit cell invasion by at least 50% and have an effective concentration of less than 100 nm in the binding affinity assay. The structures of the synthesized compounds were confirmed by spectral data.

  一系列吡啶衍生物被合成为潜在的趋化因子受体4的抑制剂。这种趋化因子受体已与各种疾病途径相关联，包括HIV-1增殖、自身免疫疾病、炎症性疾病和癌症转移。这些化合物通过亲和结合测定和抑制细胞侵袭能力的测定进行了活性测试。已确定两种命中化合物（2b和2j）进行进一步评估，这些化合物通过细胞侵袭至少抑制50%，并在亲和结合测定中的有效浓度小于100 nM。合成化合物的结构已通过光谱数据确认。