(3,4-dimethoxyphenyl)(4-(3,4-dimethoxyphenyl)-1H-imidazol-2-yl)methanone | 1187829-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4-dimethoxyphenyl)(4-(3,4-dimethoxyphenyl)-1H-imidazol-2-yl)methanone
• 英文别名: (3,4-dimethoxyphenyl)-[5-(3,4-dimethoxyphenyl)-1H-imidazol-2-yl]methanone
• CAS: 1187829-40-8
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: VLPGOMFJNVONFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3,4-dimethoxyphenyl)(4-(3,4-dimethoxyphenyl)-1H-imidazol-2-yl)methanone 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (3,4-dimethoxyphenyl)[4-(3,4-dimethoxyphenyl)-1-(prop-2-yn-1-yl)-1H-imidazol-2-yl]methanol
  参考文献：
  名称：

  咪唑-1,4-恶嗪的简单合成方案及其毒性评估

  摘要：

  AbstractImidazo‐1,5‐alkynyl alcohol derivatives were synthesized, and they were cyclized to imidazo‐1,4‐oxazines by means of cesium carbonate. Propargyl‐allene isomerization was examined, and the reaction mechanism was proposed. Moreover, cytotoxicity of synthesized molecules against LN405 cell lines was investigated by means of structure‐activity relationship (SAR). With SAR study, toxicities of some functional groups have been shown. In addition, two lead compounds were tested against DNA damaging.

  DOI：

  10.1002/hc.21412
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 selenium(IV) oxide 、 ammonium acetate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 (3,4-dimethoxyphenyl)(4-(3,4-dimethoxyphenyl)-1H-imidazol-2-yl)methanone
  参考文献：
  名称：

  一类新的碳酸酐酶抑制剂及其非锌结合的评价

  摘要：

  本研究合成了23种不同的咪唑衍生物，并首次研究了这些衍生物对碳酸酐酶I和II同工酶的抑制特性。发现咪唑衍生物的抑制浓度在 2.89-115.5 nM 范围内。对接研究检查了咪唑衍生物的结合特性，并讨论了构效关系。理论计算表明咪唑环的结合方式为非锌结合。

  DOI：

  10.1002/ardp.202100188

文献信息

• Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases
  作者：Burak Kuzu、Meltem Tan、Parham Taslimi、İlhami Gülçin、Mehmet Taşpınar、Nurettin Menges

  DOI：10.1016/j.bioorg.2019.01.044

  日期：2019.5

  Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption

  使用一锅两步策略合成单或二取代的咪唑衍生物。测试了所有咪唑衍生物的AChE和BChE抑制作用，并显示出与测试化合物多奈哌齐相似的纳摩尔活性，但比他克林的纳摩尔活性更高。进行了结构活性关系研究，对具有PDB代码1B41的AChE的X射线晶体结构的对接研究以及吸附，分布，代谢和排泄（ADME）的预测。合成的核心骨架被绑定到AChE活性位点的重要区域，例如外围阴离子位点（PAS），氧阴离子孔（OH）和阴离子亚位点（AS）。计算出报告的测试化合物的选择性，酶动力学研究表明它们具有竞争性抑制剂的作用，而其中两种测试化合物则显示出非竞争性抑制行为。ADME的预测表明，合成的分子可能会穿过血脑屏障和肠上皮屏障，并在血流中自由循环而不与人血清白蛋白结合。一种化合物对WS1（皮肤成纤维细胞）细胞系的毒性为1790 µM，而对SH-SY5Y（神经母细胞瘤）细胞系的毒性为950 µM。
• Copper-Catalyzed Synthesis of Fused Imidazopyrazine N-Oxide Skeletons
  作者：Volkan Taşdemir、Burak Kuzu、Meltem Tan、Hasan Genç、Nurettin Menges

  DOI：10.1055/s-0037-1610859

  日期：2019.2

  propargyl groups into oxime groups. N-Propargyl monooxime imidazole derivatives were cyclized by treatment with CuI to give various imidazopyrazine N-­oxides. Several copper salts, such as CuOAc, CuSO4, and CuOTf, formed the same cyclization product. This cyclization reaction occurred only in the presence of Cu(I) or Cu(II) salts; other transition metals such as Au, Ag, In, and Fe did not yield cyclic products

  N-Propargyl-2-aroylimidazoles 合成并转化为相应的酮肟。在各种条件下，通过将羰基或羰基和炔丙基转化为肟基团，形成了几种单和二酮肟咪唑衍生物。N-炔丙基单肟咪唑衍生物通过用CuI处理而环化，得到各种咪唑并吡嗪N-氧化物。几种铜盐，如 CuOAc、CuSO4 和 CuOTf，形成相同的环化产物。这种环化反应仅在 Cu(I) 或 Cu(II) 盐存在下发生；其他过渡金属如 Au、Ag、In 和 Fe 没有产生环状产物。使用核无关化学位移法计算双环的芳香性。
• Application of 3-aroyl-4(5)-arylimidazols as efficient ligands in Pd-catalyzed Heck reactions
  作者：Mojtaba AMINI、Seyedeh Motahhareh AMINI、Bagher EFTEKHARI-SIS、Ali KEIVANLOO

  DOI：10.3906/kim-1307-18

  日期：——

  The Heck coupling of haloarenes with various alkenes was successfully performed in the presence of 0.25 mol % PdCl_2 and 0.5 mol % biphenyl-4-yl-[4(5)-(biphenyl-4-yl)-1H-imidazol-2-yl]ketone 2f as a ligand with Na_2CO_3 as optimal base, in a 1:1 mixture of H_2O/DMF as the reaction solvent at 80 ^°C for 8 h. Imidazole 2f was found to be an inexpensive, air-stable, easily available, and efficient ligand in the palladium-catalyzed Heck reactions of aryl iodides (76 %--94 %), bromides (52 %--79 %), and chlorides (40 %--70 %).

  卤代芳烃与各种烯烃在0.25 mol%的PdCl_2和0.5 mol%的双苯基-4-基-[4(5)-(双苯基-4-基)-1H-咪唑-2-基]酮2f作为配体，以及Na_2CO_3为最佳碱，在1:1的H_2O/DMF混合溶剂中于80°C反应8小时，成功进行了Heck偶联反应。咪唑2f被发现是一种廉价、空气稳定、易于获取且高效的配体，在钯催化的Heck反应中对碘代芳烃（76%-94%）、溴代芳烃（52%-79%）和氯代芳烃（40%-70%）均有良好效果。
• A novel structure for ESIPT emission: Experimental and theoretical investigations
  作者：Burak Kuzu、Meltem Tan、Zeynep Ekmekci、Nurettin Menges

  DOI：10.1016/j.jphotochem.2019.111874

  日期：2019.8

  A number of substituted imidazole-based molecules were synthesized via a two-step one-pot reaction and their UV/vis and fluorescence spectra were analyzed. Emissions of the imidazole-based molecules were attributed to the excited state intramolecular proton transfer (ESIPT) process. Imidazole-based sensor molecules have high Stokes shifts which is good clue for the ESIPT mechanism. Furthermore, the

  许多取代的咪唑基分子是通过两步一锅法反应及其紫外/可见光和荧光光谱进行了分析。基于咪唑的分子的排放归因于激发态分子内质子转移（ESIPT）过程。基于咪唑的传感器分子具有较高的斯托克斯位移，这对于ESIPT机制是一个很好的线索。此外，一些控制实验证实了ESIPT机制，其中受体和供体基团被官能化，导致ESIPT发射受阻。时间分辨实验表明，合成的骨架具有不同的指数衰减，具体取决于官能团（OMe和OH）。根据时间分辨实验，ESIPT反应发生在1.0到3.10 ns之间。此外，当苯环具有OMe或OH基团时，EtOH中分子的寿命增加。计算了NH和羰基之间的二面角，发现对稳定构型很重要。ESIPT反应应中断的咪唑骨架上的甲基取代的NH基团在DMSO中的寿命为0.3 ns。使用TD-DFT分析所有化合物的势能曲线。可以看出，没有激发态质子转移的障碍，可以实现超快的ESIPT过程。
• Novel one-pot synthesis of (4 or 5)-aryl-2-aryloyl-(1H)-imidazoles in water and tauto-isomerization study using NMR
  作者：Behzad Khalili、Tahereh Tondro、Mohammed M. Hashemi

  DOI：10.1016/j.tet.2009.06.082

  日期：2009.8

  A simple and green route to synthesis of (4 or 5)-aryl-2-aryloyl-(1H)-imidazoles is described. Two isomers can tautomerize to each other by the heat absorption. The tauto-isomerization process was studied by NMR technique. Acidity and stability of products were studied using B3LYP method. (C) 2009 Elsevier Ltd. All rights reserved.