4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenol

• 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: 4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenol
• 英文别名: 2-(4-hydroxyphenyl)-5-methylbenzimidazole；4-(6-methyl-1H-1,3-benzodiazol-2-yl)phenol；4-(6-methyl-1H-benzimidazol-2-yl)phenol
• 化学式: C₁₄H₁₂N₂O
• mdl: MFCD12408725
• 分子量: 224.262
• InChiKey: CPQLMFZCFVDANN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenol 、 N,N-二乙基氯乙胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以12%的产率得到N,N-diethyl-2-[4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenoxy]ethanamine
  参考文献：
  名称：

  Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors

  摘要：

  A series of N-(2-[4-(1H-benzimidazole-2-yl)phenoxy]ethyl}substituted amine derivatives were designed to assess cholinesterase inhibitor activities. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitor activities were evaluated in vitro by using Ellman's method. It was discovered that most of the compounds displayed AChE and/or BuChE inhibitor activity and few compounds were selective against AChE/BuChE. Compound 3c and 3e were the most active compounds in the series against eeAChE and hAChE, respectively. Molecular docking studies and molecular dynamics simulations were also carried out. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.065
• 作为产物：
  描述：

  在 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenol
  参考文献：
  名称：

  2-芳基-1H-苯并[d]咪唑衍生物作为潜在微管靶向剂的合成与评价

  摘要：

  微管靶向剂（MTA）是抗癌药物发现的潜在候选药物。通过合成分子破坏微管形成或抑制解聚过程可以产生出色的抗癌候选药物。在这里，我们将 2,5-取代-1 H-苯并[d]咪唑衍生物作为潜在的秋水仙碱、诺考达唑结合位点靶向剂。使用温和的反应条件合成了大约 20 种苯并咪唑衍生物，收率 82.0%–94.0%。合成的化合物在三种细胞系中显示出中等至优异的抗癌活性，包括 Hela 细胞、A549 细胞、MRC-5 细胞。化合物B15、B16、B19和B20是三种不同细胞系中IC 50 <15 μM 的潜在候选者。在 MTT 测定中，化合物B15、B16、B19和B20显示出优异的抗增殖活性，使用 HeLa 和 A549 细胞系的 IC 50值在 5.3 ± 0.21 至 18.1 ± 0.32 μM 范围内。B15、B16、B19和B20的预测吸收、分布、代谢和排泄 (ADME) 特性和药物相似特性表

  DOI：

  10.1002/ddr.21909

文献信息

• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140037564A1

  公开（公告）日：2014-02-06

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医药用途，该化合物具有抑制酪氨酸酶的美白皮肤活性，因此适用于用于美白皮肤的药用组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药用组合物或保健食品。
• Ester derivatives of dimethylpropionic acid and pharmaceutical compositions containing them
  申请人：CERMOL S.A.

  公开号：EP1132381A1

  公开（公告）日：2001-09-12

  The present invention relates to esters of 2,2-dimethylpropionic acid having the general formula (I) or pharmacological acceptable salts thereof, as well as to pharmaceutical compositions containing said compounds and having an inhibitory activity of elastase.

  本发明涉及具有通式（I）的2,2-二甲基丙酸酯或其药理学上可接受的盐，以及含有该化合物并具有弹性蛋白酶抑制活性的药物组合物。
• Selective phenol alkylation for an improved synthesis of 2-arylbenzimidazole H4 receptor ligands
  作者：Brad M. Savall、Jill R. Fontimayor、James P. Edwards

  DOI：10.1016/j.tetlet.2009.03.033

  日期：2009.5

  free benzimidazole NH was investigated and found to be highly dependent on the substitution of the benzimidazole and phenol rings. The modification of our original synthesis of 2-arylbenzimidazole H4 receptor ligands has resulted in improved yields and ease of isolation of final products.

  研究了在游离苯并咪唑NH存在下苯酚OH的烷基化反应，发现该反应高度依赖于苯并咪唑和苯酚环的取代。我们对2-芳基苯并咪唑H 4受体配体的原始合成方法进行了改进，从而提高了收率，并易于分离最终产物。
• A facile and efficient synthesis of benzimidazole as potential anticancer agents
  作者：Thi-Kim-Chi Huynh、Thi-Hong-An Nguyen、Ngoc-Hoang-Son Tran、Thanh-Danh Nguyen、Thi-Kim-Dung Hoang

  DOI：10.1007/s12039-020-01783-4

  日期：2020.12

  simple process to synthesize and separate of 2-(substituted-phenyl) benzimidazole derivatives with high yield and efficiency. Specifically, by reacting ortho-phenylenediamines with benzaldehydes using sodium metabisulphite as an oxidation agent in a mixture of solvent under mild condition, twenty-three compounds of benzimidazoles were obtained and separated easily using hexane and water to wash, respectively

  摘要这项研究报告了一个简单的过程以高收率和高效率地合成和分离2-（取代的苯基）苯并咪唑衍生物。具体地说，通过在焦油条件下在溶剂混合物中用亚硫酸氢钠作为氧化剂使邻苯二胺与苯甲醛反应，制得二十三种苯并咪唑化合物，并分别用己烷和水洗涤容易地分离。通过FTIR，NMR和HRMS鉴定所有获得的化合物的结构。合成苯并咪唑在人肺（A549），乳腺癌（MDA-MB-231）和前列腺癌（PC3）癌细胞系上的SAR分析表明，苯并咪唑支架上5（6）位的甲基存在是一个重要因素影响抗癌活性。给电子基团（OH，OMe，–NMe的存在2，–O–CH 2 –C 6 H 5）也引起抗癌活性的显着提高，而苯并咪唑环2位苯基上的吸电子基团（–NO 2，–CF 3）的存在减少抑制合成苯并咪唑的能力。化合物2f和2g对A549和PC3细胞系均显示出显着的抗癌活性。 图形摘要通过简单的方法合成了两个系列的2-苯基苯并咪唑，并阐明了其
• Mannich-Benzimidazole Derivatives as Antioxidant and Anticholinesterase Inhibitors: Synthesis, Biological Evaluations, and Molecular Docking Study
  作者：Ayşe Selcen Alpan、Görkem Sarıkaya、Güneş Çoban、Sülünay Parlar、Güliz Armagan、Vildan Alptüzün

  DOI：10.1002/ardp.201600351

  日期：2017.7

  A series of Mannich bases of benzimidazole derivatives having a phenolic group were designed to assess their anticholinesterase and antioxidant activities. The acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activities were evaluated in vitro by using Ellman's method. According to the activity results, all of the compounds exhibited moderate to good AChE inhibitory activity

  设计了一系列具有酚基的苯并咪唑衍生物的曼尼希碱来评估它们的抗胆碱酯酶和抗氧化活性。乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 抑制活性通过使用 Ellman 方法在体外进行评估。根据活性结果，所有化合物均表现出中等至良好的AChE抑制活性（2a除外），IC50值为0.93至10.85 μM，一般表现出中等的BuChE抑制活性。此外，大多数化合物对 BuChE 具有选择性。化合物 4b 是 AChE 酶活性最强的分子，也是选择性的。此外，我们在体外研究了合成化合物对 FeCl2/抗坏血酸诱导的大鼠脑氧化应激的抗氧化作用，活性结果表明，大部分化合物作为自由基清除剂是有效的。还进行了分子对接研究和分子动力学模拟。