2-(phenoxymethyl)-1H-benzo[d]imidazole-5-carboxylic acid | 134767-72-9

• 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-(phenoxymethyl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 2-(phenoxymethyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 134767-72-9
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: ALDUIVOXWKRGLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-(phenoxymethyl)-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 [4-(2-hydroxyethyl)piperazin-1-yl]-[2-(phenoxymethyl)-3H-benzimidazol-5-yl]methanone
  参考文献：
  名称：

  Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(98)00045-7
• 作为产物：
  描述：

  苯氧乙酸 在 吡啶 、 盐酸 、 sodium hydroxide 、 氯化亚砜 、 zinc(II) chloride 作用下， 以 乙醇 、 苯 为溶剂， 反应 7.67h， 生成 2-(phenoxymethyl)-1H-benzo[d]imidazole-5-carboxylic acid
  参考文献：
  名称：

  合成一些新的苯并咪唑-5（6）-羧酸

  摘要：

  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

  DOI：

  10.1002/jhet.5570320617

文献信息

• Synthesis and Antifungal Activity of Some New Benzimidazole Derivatives
  作者：Hakan Göker、Rahmiye Ertan、Hülya Akgün、Nuran Yulug

  DOI：10.1002/ardp.19913240505

  日期：——

  Synthesis and antifungal evaluation of 5‐ethoxycarbonyl‐2‐(substituted‐benzyl or phenoxymethyl)benzimidazoles are reported. Structures of the compounds were elucidated with IR‐, 1H‐NMR‐, 13C‐NMR‐, mass‐spectra and elemental analysis. Preliminary results show that none of the synthesized benzimidazole derivatives has antifungal activity at the concentration of 100 μg/ml against Candida parapsilosis

  5-乙氧基羰基-2-（取代的-苄基或苯氧基甲基）苯并咪唑的合成和抗真菌评估报告。化合物的结构经IR、1H NMR、13C NMR、质谱和元素分析阐明。初步结果表明，合成的苯并咪唑衍生物在 100 μg/ml 浓度下均不具有抗近平滑念珠菌、星状念珠菌和假热带念珠菌的抗真菌活性。
• Discovery of a novel series of benzimidazole derivatives as diacylglycerol acyltransferase inhibitors
  作者：Kyeong Lee、Ja-Il Goo、Hwa Young Jung、Minkyoung Kim、Shanthaveerappa K. Boovanahalli、Hye Ran Park、Mun-Ock Kim、Dong-Hyun Kim、Hyun Sun Lee、Yongseok Choi

  DOI：10.1016/j.bmcl.2012.10.046

  日期：2012.12

  A novel series of benzimidazole derivatives was prepared and evaluated for their diacylglycerol acyltransferase (DGAT) inhibitory activity using microsome from rat liver. Among the newly synthesized compounds, furfurylamine containing benzimidazole carboxamide 10j showed the most potent DGAT inhibitory effect (IC50 = 4.4 mu M) and inhibited triglyceride formation in HepG2 cells. Furthermore, compound 10j reduced body weight gain of Institute of Cancer Research mice on a high-fat diet and decreased levels of total triglyceride, total cholesterol, and LDL-cholesterol in the blood accompanied with a significant increase in HDL-cholesterol level. (C) 2012 Elsevier Ltd. All rights reserved.
• 1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition
  作者：Alessandro A. Boezio、Kristin Andrews、Christiane Boezio、Margaret Chu-Moyer、Katrina W. Copeland、Erin F. DiMauro、Robert S. Foti、Robert T. Fremeau、Hua Gao、Stephanie Geuns-Meyer、Russell F. Graceffa、Hakan Gunaydin、Hongbing Huang、Daniel S. La、Joseph Ligutti、Bryan D. Moyer、Emily A. Peterson、Violeta Yu、Matthew M. Weiss

  DOI：10.1016/j.bmcl.2018.04.035

  日期：2018.6

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.
• GOKER, HAKAN;ERTAN, RAHMIYE;AKGUN, HULYA;YULUG, NURAN, ARCH. PHARM., 324,(1991) N, C. 283-286
  作者：GOKER, HAKAN、ERTAN, RAHMIYE、AKGUN, HULYA、YULUG, NURAN

  DOI：——

  日期：——
• 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