2,6-bis(2,4-dimethoxyphenyl)pyridine | 1257414-43-9

• 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: 2,6-bis(2,4-dimethoxyphenyl)pyridine
• 英文别名: 2,6-Bis(2,4-dimethoxyphenyl)pyridine
• CAS: 1257414-43-9
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: PIMGIQWLAACBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(2,4-dimethoxyphenyl)pyridine 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 乙腈 、 丁酮 为溶剂， 反应 64.25h， 生成 gold(III)(2,6-bis(2,4-didodecyloxyphenyl)pyridine)chloride
  参考文献：
  名称：

  一系列异构双（单烷氧基苯基和二烷氧基苯基）吡啶的金（III）、汞（II）和钯（II）络合物：通过金属转移和催化引入金

  摘要：

  合成并表征了一系列异构双-2,6-(单烷氧基苯基)吡啶和双-2,6-(二烷氧基苯基)吡啶配体。为了制备氯金（III）配合物，首先制备了中间体氯汞（II）配合物，但与之前研究中观察到的结果不同，之前的研究观察到它们是不纯的且最多只能获得中等产率，这里合成了纯配合物，其中许多的产率相当高。根据配体上烷氧基链的取代模式，获得单汞和/或二汞配合物，其特征在于1 H、 13 C{ 1 H} 和199 Hg NMR 光谱，以及在某些情况下通过 X射线晶体学。讨论了可能解释这种不寻常反应性的因素。在大多数情况下，相关氯金(III)络合物的金属转移反应顺利进行，尽管从双汞化前体开始时产率较低。由于这些配体对汞的倾向，人们尝试进行直接氧化，但都没有成功。然而，可以制备钯(II)的二聚体、邻位金属化络合物，并且也易于金属转移成氯金(III)络合物，从而提供无汞合成。

  DOI：

  10.1021/acs.inorgchem.3c03791
• 作为产物：
  描述：

  2,6-bis(2,4-dimethoxyphenyl)pyridine magnesium bromide 在 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 乙酸乙酯 为溶剂， 以87%的产率得到2,6-bis(2,4-dimethoxyphenyl)pyridine
  参考文献：
  名称：

  Electron transfer studies on Cu(II) complexes bearing phenoxy-pincer ligands

  摘要：

  Oxido-pincer ligands with phenolate-groups [2,6-bis(2-methoxyphenyl) pyridine (LOMe2), 2,6-bis(2-hydroxyphenyl)- pyridine (LOH2), 2,6-bis-(2,4-dimethoxyphenyl)-pyridine (LOMe4)] coordinate to Cu-II forming binuclear complexes which can be easily and reliably converted into mononuclear species. Their physical properties were analysed using EPR, optical spectroscopy and (spectro-) electrochemical methods. The results were compared to those of related Ni-II complexes and discussed in view of Cu-containing metalloenzymes. Due to the ligands flexibility the Cu-II/Cu-I redox couple exhibits high reversibility, while the ligand-centred oxidation leads to highly reactive phenoxy radicals. Reduction of the LOH2 complex leads to sequential deprotonation. The ligand LOMe4 and the derived complexes show blue luminescence, which can be rationalised from its molecular structure (analysed by XRD). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.06.011

文献信息

• Design, Synthesis, and Biological Evaluation of Novel Pyridine-Bridged Analogues of Combretastatin-A4 as Anticancer Agents
  作者：Shilong Zheng、Qiu Zhong、Madhusoodanan Mottamal、Qiang Zhang、Changde Zhang、Elise LeMelle、Harris McFerrin、Guangdi Wang

  DOI：10.1021/jm500002k

  日期：2014.4.24

  A series of novel pyridine-bridged analogues of combretastatin-A4 (CA-4) were designed and synthesized. As expected, the 4-atom linker configuration retained little cytotoxicities in the compounds 2e, 3e, 3g, and 4i. Activities of the analogues with 3-atom linker varied widely depending on the phenyl ring substitutions, and the 3-atom linker containing nitrogen represents the more favorable linker

  设计并合成了一系列新型吡啶桥连的考布他汀-A4 (CA-4) 类似物。正如预期的那样，4 原子接头构型在化合物2e、3e、3g和4i 中几乎没有细胞毒性。具有 3 原子接头的类似物的活性因苯环取代而有很大差异，含氮的 3 原子接头代表更有利的接头结构。其中，三种类似物（4h、4s和4t）以与 CA-4 相当的方式在体内有效抑制细胞存活和生长、阻止细胞周期并阻断血管生成和脉管系统形成。叠加4H和微管蛋白的秋水仙碱结合口袋中的4s显示 CA- 4、4h和4s的结合姿势是相似的，正如竞争性结合试验所证实的，其中测量了配体替代微管蛋白结合的秋水仙碱的能力。结合数据与观察到的抗增殖和抑制血管生成的生物活性一致，但不能预测它们的抗微管蛋白聚合活性。
• [EN] ANTI-VASCULATURE AND ANTI-TUBULIN COMBRETASTATIN ANALOGS FOR TREATMENT OF CANCER<br/>[FR] ANALOGUES DE COMBRÉTASTATINE ANTI-VAISSEAUX SANGUINS ET ANTI-TUBULINE POUR LE TRAITEMENT DU CANCER
  申请人：XAVIER UNIVERSITY OF LOUISIANA

  公开号：WO2015153252A1

  公开（公告）日：2015-10-08

  Combretastatins analog compounds and their pharmaceutically acceptable salts are presented, as well as pharmaceutical compositions comprising the combretastatin analog compounds and uses of the combretastatin analog compounds, either alone or in combination with at least one additional therapeutic agent, in the treatment of cancer, and in particular cancer presenting as metastatic tumors.

  提供了Combretastatins类似化合物及其药用可接受的盐，以及包含Combretastatins类似化合物的药物组合物，以及Combretastatins类似化合物的用途，无论是单独使用还是与至少一种额外治疗剂联合使用，用于治疗癌症，特别是表现为转移性肿瘤的癌症。
• Anti-vasculature and anti-tubulin combretastatin analogs for treatment of cancer
  申请人：XAVIER UNIVERSITY OF LOUISIANA

  公开号：US10017475B2

  公开（公告）日：2018-07-10

  Combretastatins analog compounds and their pharmaceutically acceptable salts are presented, as well as pharmaceutical compositions comprising the combretastatin analog compounds and uses of the combretastatin analog compounds, either alone or in combination with at least one additional therapeutic agent, in the treatment of cancer, and in particular cancer presenting as metastatic tumors.

  本研究介绍了考布他汀类似物化合物及其药学上可接受的盐类，以及包含考布他汀类似物化合物的药物组合物和考布他汀类似物化合物在治疗癌症，特别是以转移性肿瘤为表现形式的癌症中单独使用或与至少一种额外治疗剂联合使用的用途。
• ANTI-VASCULATURE AND ANTI-TUBULIN COMBRETASTATIN ANALOGS FOR TREATMENT OF CANCER
  申请人：WANG Guangdi

  公开号：US20170044103A1

  公开（公告）日：2017-02-16

  Combretastatins analog compounds and their pharmaceutically acceptable salts are presented, as well as pharmaceutical compositions comprising the combretastatin analog compounds and uses of the combretastatin analog compounds, either alone or in combination with at least one additional therapeutic agent, in the treatment of cancer, and in particular cancer presenting as metastatic tumors.
• Electron transfer studies on Cu(II) complexes bearing phenoxy-pincer ligands
  作者：Axel Klein、Katharina Butsch、Jörg Neudörfl

  DOI：10.1016/j.ica.2010.06.011

  日期：2010.10

  Oxido-pincer ligands with phenolate-groups [2,6-bis(2-methoxyphenyl) pyridine (LOMe2), 2,6-bis(2-hydroxyphenyl)- pyridine (LOH2), 2,6-bis-(2,4-dimethoxyphenyl)-pyridine (LOMe4)] coordinate to Cu-II forming binuclear complexes which can be easily and reliably converted into mononuclear species. Their physical properties were analysed using EPR, optical spectroscopy and (spectro-) electrochemical methods. The results were compared to those of related Ni-II complexes and discussed in view of Cu-containing metalloenzymes. Due to the ligands flexibility the Cu-II/Cu-I redox couple exhibits high reversibility, while the ligand-centred oxidation leads to highly reactive phenoxy radicals. Reduction of the LOH2 complex leads to sequential deprotonation. The ligand LOMe4 and the derived complexes show blue luminescence, which can be rationalised from its molecular structure (analysed by XRD). (C) 2010 Elsevier B.V. All rights reserved.