2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid | 174422-18-5

• 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: 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 2-(4-phenylmethoxyphenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 174422-18-5
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: HGLQZMHFAPHBJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.047
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid 在 氯化亚砜 作用下， 以 氯仿 、 苯 为溶剂， 反应 2.5h， 生成 [2-(4-Benzyloxy-phenyl)-1H-benzoimidazol-5-yl]-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Some New 2-Phenyl-N-substituted Carboxamido-1H-benzimidazole Derivatives

  摘要：

  Some 1H-benzimidazole-carboxamide derivatives were prepared and their antimicrobial activities against Staphyloccus aureus, Escherichia coli and Candida albicans evaluated. Compounds 18, 22, and 25 exhibited the best activity against Candida albicans.

  DOI：

  10.1002/1521-4184(200105)334:5<148::aid-ardp148>3.0.co;2-s
• 作为产物：
  描述：

  对羟基苯甲醛 在 sodium metabisulfite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.5h， 生成 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid
  参考文献：
  名称：

  NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

  摘要：

  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。

  公开号：

  US20140037564A1

文献信息

• Synthesis of some new benzimidazole-5(6)-carboxylic acids
  作者：Hakan Göker、Süreyya Ölgen、Rahmiye Ertand、HÜLya Akgün、Süheyla Özbey、Engin Kendi、GÜL Topçu

  DOI：10.1002/jhet.5570320617

  日期：1995.11

  The title compounds, 1,2-dialkyl-benzimidazole-5(6)-carboxylic acids 34–45 were prepared at four steps; 1) preparation of mono amide derivatives 1–11 by the reaction of methyl 3,4-diaminobenzoate and substituted phenyl or phenoxyacetic acid chlorides; 2) preparation of the methyl benzimidazolecarboxyl-ates 12–22, with zinc chloride and dry hydrogen chloride gas; 3) alkaline hydrolysis of the esters

  标题化合物1,2-二烷基苯并咪唑-5（6）-羧酸34-45的制备分为四个步骤；1）通过3,4-二氨基苯甲酸甲酯与取代的苯基或苯氧乙酸氯的反应制备单酰胺衍生物1-11；2）用氯化锌和干燥的氯化氢气体制备苯并咪唑甲酸甲酯12-22。3）酯23-33的碱水解；4）在碱性介质中用苄基或对氟苄基溴取代咪唑环。2-芳基苯并咪唑-5-（6） -羧酸50-53制备通过 3,4-二氨基苯甲酸和芳香醛与铜离子的氧化缩合反应
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREOF
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：US20150366776A1

  公开（公告）日：2015-12-24

  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、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有抑制酪氨酸酶的美白活性，因此可用于美白药物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于制备有效预防和治疗肥胖症、代谢性疾病或心血管疾病的药物组合物或保健食品。
• Synthesis of Some 2-Substituted-5-(Benzothiazol-2-yl)-1H-Benzimidazole Derivatives and Investigation of Their Antiproliferative Effects
  作者：Bilge Uzun Polat、Ulviye Acar Çevik、Miriş Dikmen、Yusuf Özkay

  DOI：10.1007/s11094-022-02658-3

  日期：2022.7

  In addition to methods such as radiotherapy and surgery, another effective way that is preferred for the treatment of cancer is based on the use of chemotherapeutic agents. Although there are more than hundred drugs for cancer treatment, there is still a need to develop new anticancer drugs because of reasons such as drug resistance, side effects, low selectivity and severe toxicity. Benzimidazole and benzothiazole ring systems are the basis of chemical structures of many important drugs because of their different pharmacological properties. In this work, due to potential anticancer effects of benzothiazole and benzimidazole ring systems, eight new compounds that contain both these ring systems in the same chemical structure were synthesized. The structures of obtained compounds were characterized by the IR, NMR, and mass spectroscopy and by elemental analysis data. Cytotoxic effects of the synthesized compounds were tested on Caco-2 (ATCC HTB-37), A549 (ATCC CCL-185) and NIH3T3 (ATCC CRL-1658) cell lines. Two compounds (3c and 3e) were determined as the most effective agents that showed activity comparable with that of the reference drug Cisplatin.

  除了放疗和手术等方法外，另一种治疗癌症的有效方法是使用化疗药物。虽然目前治疗癌症的药物已超过百种，但由于耐药性、副作用、选择性低和毒性大等原因，仍需要开发新的抗癌药物。苯并咪唑和苯并噻唑环系统因其不同的药理特性，成为许多重要药物的化学结构基础。由于苯并噻唑和苯并咪唑环系统具有潜在的抗癌作用，本研究合成了 8 个在同一化学结构中含有这两种环系统的新化合物。通过红外光谱、核磁共振和质谱以及元素分析数据对所获化合物的结构进行了表征。在 Caco-2 (ATCC HTB-37)、A549 (ATCC CCL-185) 和 NIH3T3 (ATCC CRL-1658) 细胞系上测试了合成化合物的细胞毒性作用。两个化合物（3c 和 3e）被确定为最有效的药物，其活性与参考药物顺铂相当。
• Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity
  作者：Hakan Göker、Meral Tunçbilek、Gülgün Ayhan、Nurten Altanlar

  DOI：10.1016/s0014-827x(98)00045-7

  日期：1998.6

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.
• Goeker, Hakan; Tebrizli, Emin; Abbasoglu, Ufuk, Il Farmaco, 1996, vol. 51, # 1, p. 53 - 58
  作者：Goeker, Hakan、Tebrizli, Emin、Abbasoglu, Ufuk

  DOI：——

  日期：——