1-(4-methoxybenzyl)-2-methyl-1H-benzo[d]imidazole | 114963-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4-methoxybenzyl)-2-methyl-1H-benzo[d]imidazole
• 英文别名: 1-(4-methoxybenzyl)-2-methyl-1H-benzimidazole；1-[(4-methoxyphenyl)methyl]-2-methylbenzimidazole
• CAS: 114963-96-1
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: DEWIBSSWWNXZEY-UHFFFAOYSA-N

物化性质

• 沸点：
  452.8±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)-2-methyl-1H-benzo[d]imidazole 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以62%的产率得到1-p-methoxybenzylbenzimidazole-2-carboxaldehyde
  参考文献：
  名称：

  在四个唑取代基的卟啉的内消旋的X射线晶体结构：位置内消旋-卟啉在200K的-tetrakis-（1- benzylpyrazol -4-基）

  摘要：

  使用已建立的方法已经以提高的收率制备了几种新的卟啉，该方法适用于带有吡唑N 1-氮保护基的甲酰基吡唑。的脱保护的N-对甲氧基苄基和SEM保护的内消旋-pyrazolylporphyrins得到与吡唑游离N的第一个已知pyrazolylporphyrins ħ组。通过X射线分析已经解析了内消旋-四（-1-）（苄基-吡唑-4-基）卟啉4a的晶体和分子结构。卟啉核显示出与中观相似的键距和键角-四苯基卟啉本身。吡唑环几乎垂直于大环，使得吡唑N 2原子的氮原子孤对（ααββ阻转异构体）位于其上，下，下，上。

  DOI：

  10.1016/0040-4020(95)00159-6
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以51%的产率得到1-(4-methoxybenzyl)-2-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

  摘要：

  The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell sternness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.

  DOI：

  10.1021/acs.jmedchem.5b01741

文献信息

• Tetranuclear Palladium Complexes of Abnormal <i>N</i> ‐Heterocyclic Carbene Ligands and their Catalytic Activities in Mizoroki‐Heck Coupling Reaction of Electron‐Rich Aryl Chlorides
  作者：Jhen‐Yi Lee、Yong‐Siang Su、Yu‐Shan Wang、Hon Man Lee

  DOI：10.1002/adsc.201900805

  日期：2019.10.22

  imidazolyl/benziimidazolyl moiety and a N‐CH2C(=O)NHPh substituent, two series of ligand precursors with ortho hydroxy groups incorporated on the N‐phenyl rings were prepared. The structural fine tuning of the ligand scaffold allowed the synthesis of tetranuclear palladium complexes with abnormal N‐heterocyclic carbene (aNHC) ligands. For precursors with C2‐methyl blocking groups, pyridine‐assisted C−H bond activation

  基于咪唑基/苯并咪唑基部分的配体骨架和一个N- CH 2 C（= O）NHPh取代基，制备了两个在N-苯基环上结合有邻羟基的配体前体系列。该配体的支架的结构微调允许与异常四核钯络合物的合成Ñ -杂环卡宾（一个NHC）配体。对于具有C2-甲基封闭基团的前体，吡啶辅助的CH键活化导致形成单核三齿钯a NHC复合物或具有三齿CNO供体的四核复合物。代表性的单核和四核钯aNHC配合物通过X射线衍射研究进行了结构表征，揭示了非常短的Pd-C键距。四核钯a NHC络合物在催化Mizoroki-Heck偶联反应方面非常有效，并且能够使用一系列芳基氯化物，包括失活的底物，钯载量低至0.2 mol％。
• Palladium-Catalyzed Asymmetric Allylic Alkylations of Polynitrogen-Containing Aromatic Heterocycles
  作者：Barry M. Trost、David A. Thaisrivongs、Jan Hartwig

  DOI：10.1021/ja205523e

  日期：2011.8.17

  palladium-catalyzed asymmetric allylic alkylation (AAA) reaction of a variety of nitrogen-containing aromatic heterocycles, including pyrazine, pyrimidine, pyridazine, quinoxaline, and benzoimidazole derivatives. The mesityl ester, whose steric bulk prevents competitive deacylation of the electrophile from "hard" nucleophiles, is introduced as a new leaving group in allylic alkylation chemistry. In contrast to

  我们报告了钯催化的各种含氮芳香杂环的不对称烯丙基烷基化 (AAA) 反应，包括吡嗪、嘧啶、哒嗪、喹喔啉和苯并咪唑衍生物。在烯丙基烷基化化学中作为新的离去基团引入了甲基酯，其空间体积可以防止亲电试剂与“硬”亲核试剂的竞争性脱酰。与我们之前对基于吡啶的底物的 AAA 反应的研究相比，在用 LiHMDS 去质子化之前不需要与路易斯酸进行预络合，这强调了这些缺电子亲核试剂的相对酸性。
• New amino-alkyl-amide derivatives as CCR3 receptor ligands
  申请人：PAPPNE BEHR Agnes

  公开号：US20080293745A1

  公开（公告）日：2008-11-27

  The invention relates to a compound of the general formula (I), as defined herein which is useful for the treatment of a pathology in a patient wherein a CCR3 receptor plays a role in the development of the pathology, and pharmaceutical preparations containing such compound. The invention is also directed to a process for preparing the compound of the general formula (I), and intermediate useful in the preparation.

  本发明涉及一种通式(I)所定义的化合物，其对于治疗患者中CC3受体在病理发展中起作用的病理学是有用的，并且包含这种化合物的制药制剂。本发明还涉及一种制备通式(I)的化合物的方法，以及用于制备的中间体。
• [EN] AMINO-ALKYL-AMIDE DERIVATIVES AS CCR3 RECEPTOR LIGANDS<br/>[FR] DERIVES D'AMINO-ALKYL-AMIDE UTILISES COMME LIGANDS DE RECEPTEUR CCR3
  申请人：SANOFI AVENTIS

  公开号：WO2007034251A1

  公开（公告）日：2007-03-29

  [EN] The present invention relates to the CCR3 receptor ligands of the general formula (I), within them favourably to antagonists and to the salts, solvates and isomers thereof, to the pharmaceutical compositions containing them, to the use of the compounds of the general formula (I) and their salts, solvates and isomers, to the preparation of the compounds of the general formula (I) and their salts, solvates and isomers and to the new intermediates of the general formula (III).
  [FR] La présente invention concerne des ligands de récepteur CCR3 de formule générale (I), des antagonistes, sels, solvates et isomères de ceux-ci, des compositions pharmaceutiques les contenant, l'utilisation des composés de formule générale (I) et de leurs sels, solvates et isomères, un procédé pour préparer les composés de formule générale (I) et leurs sels, solvates et isomères, ainsi que de nouveaux produits intermédiaires de formule générale (III).
• Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1
  作者：Sabin Llona-Minguez、Andreas Höglund、Sylvain A. Jacques、Lars Johansson、José Manuel Calderón-Montaño、Magnus Claesson、Olga Loseva、Nicholas C. K. Valerie、Thomas Lundbäck、Javier Piedrafita、Giovanni Maga、Emmanuele Crespan、Laurent Meijer、Estefanía Burgos Morón、Pawel Baranczewski、Ann-Louise Hagbjörk、Richard Svensson、Elisee Wiita、Ingrid Almlöf、Torkild Visnes、Fredrik Jeppsson、Kristmundur Sigmundsson、Annika Jenmalm Jensen、Per Artursson、Ann-Sofie Jemth、Pål Stenmark、Ulrika Warpman Berglund、Martin Scobie、Thomas Helleday

  DOI：10.1021/acs.jmedchem.5b01741

  日期：2016.2.11

  The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell sternness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.