4-(4-methoxyphenyl)-1-methyl-1H-imidazole | 40688-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-methoxyphenyl)-1-methyl-1H-imidazole
• 英文别名: 1-methyl-4-(4-methoxyphenyl)imidazole；4-(4-Methoxyphenyl)-1-methylimidazole
• CAS: 40688-49-1
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: IWUMIMWFLSUQER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-(4-methoxyphenyl)-1-methyl-1H-imidazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到4-(1-methyl-1H-imidazol-4-yl)phenol
  参考文献：
  名称：

  靶向结核分枝杆菌肌苷 5'-单磷酸脱氢酶 (IMPDH) 的基于片段的方法。

  摘要：

  结核病 (TB) 仍然是全世界死亡的主要原因，需要改进治疗以对抗耐药性的出现。肌苷 5'-单磷酸脱氢酶 (IMPDH) 是从头合成鸟嘌呤核苷酸所需的关键酶，是一种有吸引力的结核病药物靶点。在这里，我们描述了使用基于片段的筛选和基于结构的设计技术来鉴定有效的 IMPDH 抑制剂。筛选耐热分枝杆菌 (Mth) IMPDH ΔCBS 抑制剂的片段库确定了一种低亲和力苯基咪唑衍生物。第 M 个 IMPDH ΔCBS-IMP-抑制剂复合物的 X 射线晶体学显示该片段的两个分子结合在 IMPDH 的 NAD 结合口袋中。

  DOI：

  10.1021/acs.jmedchem.7b01622
• 作为产物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 在 氢氧化钾 、 氨 作用下， 以 丙酮 为溶剂， 反应 5.12h， 生成 4-(4-methoxyphenyl)-1-methyl-1H-imidazole
  参考文献：
  名称：

  Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds

  摘要：

  Polycarpine 1, a highly cytotoxic marine natural product, has been synthesized in three steps from p-methoxyphenacyl bromide 4 in 57% overall yield. The key reaction for construction of the symmetrically substituted disulfide linkage of polycarpine is the treatment of 2-amino-4-(4-methoxyphenyl)-1-methylimidazole 17 with S2Cl2 in acetic acid. In a similar way ten related compounds, including three thiazole analogues, have been prepared. Most of them exhibit high cytotoxic activities against an array of human cancer cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00668-0

文献信息

• [EN] VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE PROTÉINE 1 D'ADHÉSION VASCULAIRE (VAP -1) ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2020006177A1

  公开（公告）日：2020-01-02

  Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文披露了小分子血管粘附蛋白-1（VAP-1）调节剂组合物、药物组合物及其使用和制备方法。
• Regioselective Synthesis of 4,5-Diaryl-1-methyl-1<i>H</i>-imidazoles Including Highly Cytotoxic Derivatives by Pd-Catalyzed Direct C-5 Arylation of 1-Methyl-1<i>H</i>-imidazole with Aryl Bromides
  作者：Fabio Bellina、Silvia Cauteruccio、Annarita Di Fiore、Renzo Rossi

  DOI：10.1002/ejoc.200800738

  日期：2008.11

  A general and efficient three-step procedure for the highly regioselective synthesis of 1-methyl-1H-imidazoles possessing electron-rich, electron-neutral, and/or electron-deficient aryl moieties at their 4- and 5-positions is described. The first step involves the Pd-catalyzed direct C-5 arylation of commercially available 1-methyl-1H-imidazole with aryl bromides, and the second and third steps of

  描述了在 4 位和 5 位具有富电子、电子中性和/或缺电子芳基部分的 1-甲基-1H-咪唑的高度区域选择性合成的通用和有效的三步法。第一步涉及 Pd 催化的市售 1-甲基-1H-咪唑与芳基溴化物的直接 C-5 芳基化，该序列的第二步和第三步涉及所得 5-芳基的选择性 C-4 溴化。 1-甲基-1H-咪唑与NBS，然后是PdCl2(dppf)-催化的5-芳基-4-溴-1-甲基-1H-咪唑和芳基硼酸在相转移条件下的铃木型反应。如此制备的两种 4,5-二芳基-1-甲基-1H-咪唑，可被视为天然存在的考布他汀 A-4 (CA-4) 的 Z 限制类似物，已证明对多种人类肿瘤细胞系具有高度细胞毒性，并且这些衍生物之一已被证明比 CA-4 和迄今为止文献中研究的所有咪唑衍生物更具细胞毒性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany
• Beta-agonists, methods for the preparation thereof and their use as pharmaceutical compositions
  申请人：Trieselmann Thomas

  公开号：US20080234278A1

  公开（公告）日：2008-09-25

  The present invention relates to new beta-agonists of general formula (I) wherein the groups R 1 to R 7 have the meanings given in the claims and specification, the tautomers, the enantiomers, the diastereomers, the mixtures thereof, the prodrugs thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, processes for preparing these compounds and their use as pharmaceutical compositions.

  本发明涉及通式（I）的新型β-激动剂，其中R1至R7的基团具有权利要求书和说明书中所给出的含义，它们的互变异构体、对映异构体、顺反异构体、混合物、前药及其盐，特别是与无机或有机酸或碱的生理上可接受的盐，制备这些化合物的过程以及它们作为药物组成物的用途。
• Imidazole analogues of resveratrol: synthesis and cancer cell growth evaluation
  作者：Fabio Bellina、Nicola Guazzelli、Marco Lessi、Chiara Manzini

  DOI：10.1016/j.tet.2015.02.024

  日期：2015.4

  Novel trans-restricted analogues of resveratrol in which the C-C double bond of the natural derivative has been replaced by diaryl substituted imidazole analogues have been designed. The syntheses of 1,4-, 2,4-, and 2,5-diarylimidazoles, in which the two aryl moieties are linked to the heteroaromatic core in a 1,3 fashion in order to preserve the trans stereochemistry, have been successfully carried out by regioselective sequential transition metal-catalyzed arylations of simple, commercially available imidazole precursors. The anticancer activity of selected analogues has been evaluated in vitro against the NCI-60 human tumor cell lines panel. From this screening, we were able to select a synthetic candidate that resulted more active than its natural lead. (C) 2015 Elsevier Ltd. All rights reserved.
• Horne, David A.; Yakushijin, Kenichi; Buechi, George, Heterocycles, 1994, vol. 39, # 1, p. 139 - 154
  作者：Horne, David A.、Yakushijin, Kenichi、Buechi, George

  DOI：——

  日期：——