2-乙基-5-甲氧基-1H-苯并咪唑 | 23073-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-乙基-5-甲氧基-1H-苯并咪唑
• 英文名称: 2-ethyl-5-methoxy-1H-benzo[d]imidazole
• 英文别名: 2-ethyl-5-methoxybenzimidazole；5-methoxy-2-ethylbenzimidazole；2-ethyl-6-methoxy-1H-benzimidazole
• CAS: 23073-50-9
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: AAXILYPOZBBCEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙基-5-甲氧基-1H-苯并咪唑 在 potassium carbonate 、 sodium iodide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2-ethyl-5-methoxy-1-(4-phenoxybutyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Identification of Phenoxyalkylbenzimidazoles with Antitubercular Activity

  摘要：

  We conducted an evaluation of the phenoxyalkylbenzimidazole series based on the exemplar 2-ethyl-1-(3-phenoxypropyl)-1H-benzo[d]imidazole for its antitubercular activity. Four segments of the molecule were examined systematically to define a structure activity relationship with respect to biological activity. Compounds had submicromolar activity against Mycobacterium tuberculosis; the most potent compound had a minimum inhibitory concentration (MIC) of 52 nM and was not cytotoxic against eukaryotic cells (selectivity index = 523). Compounds were selective for M. tuberculosis over other bacterial species, including the closely related Mycobacterium smegmatis. Compounds had a bacteriostatic effect against aerobically grown, replicating M. tuberculosis, but were bactericidal against nonreplicating bacteria. Representative compounds had moderate to high permeability in MDCK cells, but were rapidly metabolized in rodents and human liver microsomes, suggesting the possibility of rapid in vivo hepatic clearance mediated by oxidative metabolism. These results indicate that the readily synthesized phenoxyalkylbenzimidazoles are a promising class of potent and selective antitubercular agents, if the metabolic liability can be solved.

  DOI：

  10.1021/acs.jmedchem.5b00546
• 作为产物：
  描述：

  丙醇 、 2-硝基-4-甲氧基苯胺 在 palladium with copper supported on alumina 作用下， 以 水 为溶剂， 179.84 ℃ 、3.5 MPa 条件下， 反应 12.0h， 以96.8%的产率得到2-乙基-5-甲氧基-1H-苯并咪唑
  参考文献：
  名称：

  Cu-Pd /γ-Al2O3催化多步反应的偶联：苯并咪唑衍生物的直接合成

  摘要：

  非均相催化剂催化的多步反应的偶联是完成一些非常规化学转化的重要途径。由于先前步骤产生的起始原料被吸附在...上

  DOI：

  10.1039/c6ra13004f

文献信息

• Ag–TiO₂/Clay Composite Photocatalyst for the Oxidation–Cyclization of 1,2-Diamine Compounds with Propylene Glycol or Alcohols
  作者：Kaliyamoorthy Selvam、Mari Annadhasan、Rengasamy Velmurugan、Meenakshisundaram Swaminathan

  DOI：10.1246/bcsj.20090319

  日期：2010.7.15

  Silver-loaded TiO2 (Ag–TiO2) and acidic clay (K10 montmorillonite) composite photocatalyst has been successfully applied for the light-induced conversion of o-phenylenediamine (OPD) and its derivatives to substituted benzimidazoles with various alcohols in acetonitrile using UV-A and solar light. The influence of the various photocatalysts, solvents, and substituents on the yield and selectivity of the products has been investigated. The mechanism of photocatalysis is proposed. Loading silver on TiO2 enhances product yield and selectivity both in UV and solar light. In the presence of primary alcohols, 2-aminothiophenol forms only disulfide and hence Ag–TiO2/clay can be used as a green catalyst for the synthesis of disulfides.

  负载银的TiO2（Ag–TiO2）和酸性粘土（K10蒙脱石）复合光催化剂已成功应用于紫外A和太阳光诱导的邻苯二胺（OPD）及其衍生物与多种醇在乙腈中的光催化转化合成取代苯并咪唑。考察了不同光催化剂、溶剂和取代基对产物收率和选择性的影响。提出了光催化机理。在TiO2上负载银可以提高紫外和太阳光下产物的收率和选择性。在存在一级醇的情况下，2-氨基硫酚仅形成二硫化物，因此Ag–TiO2/粘土可用作合成二硫化物的绿色催化剂。
• INDOLE DERIVATIVES AS CRAC MODULATORS
  申请人：Alam Muzaffar

  公开号：US20110071150A1

  公开（公告）日：2011-03-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 and R 4 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with calcium release-activated calcium channels (CRAC).

  公式I的化合物： 或其药用可接受的盐， 其中R1、R2、R3和R4按本文定义。还公开了制造这些化合物的方法以及使用这些化合物治疗与钙释放激活钙通道（CRAC）相关疾病的用途。
• Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides
  作者：Juan J. Rojas、Rosemary A. Croft、Alistair J. Sterling、Edward L. Briggs、Daniele Antermite、Daniel C. Schmitt、Luka Blagojevic、Peter Haycock、Andrew J. P. White、Fernanda Duarte、Chulho Choi、James J. Mousseau、James A. Bull

  DOI：10.1038/s41557-021-00856-2

  日期：2022.2

  This disconnection, comparable to a typical amidation, will allow the application of vast existing amine libraries. The reaction is tolerant to a wide range of polar functionalities and is suitable for array formats. Ten oxetane analogues of bioactive benzamides and marketed drugs are prepared. Kinetic and computational studies support the formation of an oxetane carbocation as the rate-determining

  生物等排体提供了有价值的设计元素，药物化学家可以使用这些元素将生物活性化合物的结构和药代动力学特征调整为可行的候选药物。芳基氧杂环丁胺作为苯甲酰胺（非常常见的药效团）的生物等排体具有令人兴奋的潜力，但由于缺乏可用的合成方法而很少被检查。在这里，我们描述了磺酰氟通过已建立的 SuFEx（磺酰氟交换）点击反应性的替代途径形成氨基氧杂环丁烷的一类反应。脱氟磺酰化仅在加热时形成平面氧杂环丁烷碳正离子。这种断开与典型的酰胺化相当，将允许应用大量现有的胺库。该反应对多种极性官能团具有耐受性，适用于阵列形式。制备了十种具有生物活性的苯甲酰胺和已上市药物的氧杂环丁烷类似物。动力学和计算研究支持氧杂环丁烷碳正离子的形成作为速率决定步骤，然后是化学选择性亲核偶联步骤。
• QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  申请人：Cook, II James H.

  公开号：US20090270405A1

  公开（公告）日：2009-10-29

  The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the nicotinic α7 receptor and may be useful for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.

  该披露提供了公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物是烟碱性α7受体的配体，可能对治疗中枢神经系统的各种疾病，特别是情感和神经退行性疾病，有用。
• 一种基于邻苯二胺环化的苯并咪唑类化合物制 备方法
  申请人：大连理工大学

  公开号：CN103910682B

  公开（公告）日：2016-03-02

  本发明属于精细化工领域，涉及一种苯并咪唑化合物的合成方法改进及相关化学技术。其特征在于：使用邻苯二胺和1,3-二羰基化合物为原料，在质子酸催化下合成苯并咪唑化合物。本发明主要是提供一种新的合成苯并咪唑化合物的方法，该方法具有反应条件温和、方法步骤简单、原料易得、官能团兼容性好等优点。由于苯并咪唑是一种重要的生物活性基团，在药学领域有着非常广泛的应用；因此，本发明具有较大的使用价值和社会经济效益。