ethyl 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate | 89457-09-0

• 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: ethyl 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-2-trifluoromethylbenzimidazole；ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate；ethyl 2-(trifluoromethyl)-3H-benzimidazole-5-carboxylate
• CAS: 89457-09-0
• 化学式: C₁₁H₉F₃N₂O₂
• 分子量: 258.2
• InChiKey: WOQXCSGTWFKUSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  ethyl 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(三氟甲基)-1H-苯并[D]咪唑-6-甲醛
  参考文献：
  名称：

  [EN] MAP4K4 (HGK) Inhibitors
  [FR] INHIBITEURS DE MAP4K4 (HGK)

  摘要：

  该发明提供了有丝分裂原激活蛋白激酶激酶激酶激酶4（MAP4K4）抑制剂，以及其药用盐、氢化物和立体异构体。这些化合物被用于制备药物组合物，并用于制备方法，包括使用有效量的该化合物或组合物治疗需要的人，以及检测结果肿瘤细胞生长、癌症或转移的减少。

  公开号：

  WO2016114816A1
• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 盐酸 、 甲酸 、 硫酸 作用下， 以 水 为溶剂， 生成 ethyl 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

  摘要：

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.004

文献信息

• Benzimidazole compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06352985B1

  公开（公告）日：2002-03-05

  A benzimidazole compound represented by the formula (I): wherein R3 is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.

  一种由公式（I）表示的苯并咪唑化合物：其中R3是一个羧基、酯化羧基、酰胺化羧基、氨基、酰胺基或磺酰基，或其药学上可接受的盐。由于它们具有降低血糖作用或PDE5抑制作用，这些化合物或其盐可用作治疗糖耐量受损、糖尿病、糖尿病并发症、胰岛素抵抗综合征、高脂血症、动脉粥样硬化、心血管疾病、高血糖或高血压的药物；或心绞痛、高血压、肺动脉高压、充血性心力衰竭、肾小球病、肾小管间质疾病、肾功能衰竭、动脉粥样硬化、血管狭窄、远端血管病、脑卒中、慢性可逆性梗阻、过敏性鼻炎、荨麻疹、青光眼、以肠蠕动障碍为特征的疾病、阳痿、糖尿病并发症、肾炎、癌性消瘦或PTCA后再狭窄的药物。
• Benzimidazole derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06166219A1

  公开（公告）日：2000-12-26

  Novel benzimidazole derivatives represented by the formula (I): ##STR1## wherein R.sub.3 is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.

  新型苯并咪唑衍生物的化学式（I）表示如下：##STR1##其中R.sub.3是一个羧基、酯化羧基、酰胺化羧基、氨基、酰胺基或磺酰基，或它们的药学上可接受的盐。由于它们具有降低血糖作用或PDE5抑制作用，这些化合物或其盐可用作治疗糖耐量受损、糖尿病、糖尿病并发症、胰岛素抵抗综合征、高脂血症、动脉粥样硬化、心血管疾病、高血糖或高血压的药物；或心绞痛、高血压、肺动脉高压、充血性心力衰竭、肾小球病、肾小管间质疾病、肾功能衰竭、动脉粥样硬化、血管狭窄、远端血管病变、脑卒中、慢性可逆性梗阻、过敏性鼻炎、荨麻疹、青光眼、以肠动力障碍为特征的疾病、阳痿、糖尿病并发症、肾炎、癌性消瘦或PTCA后再狭窄的药物。
• Fe(OTf) 3 -catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o -arylenediamines and hexafluoroacetylacetone
  作者：Yanmei Zhou、Guanshuo Shen、Yuebo Sui、Haifeng Zhou

  DOI：10.1016/j.tetlet.2016.06.086

  日期：2016.7

  An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure

  已经开发出铁催化的实际合成方法，即通过邻芳基二胺和六氟乙酰丙酮的缩合，然后分子内加成和一锅中C–C键的裂解，合成2-三氟甲基芳基咪唑。获得了一系列标题化合物，产率高达99％。由于简单的实验程序和容易获得的试剂，该方法非常实用并且适合于可扩展的制备。
• Nouvelle voie de synthèse des 2-trifluorométhylarylimidazoles sur montmorillonite K10 en ‘milieu sec’ sous micro-onde
  作者：Khalid Bougrin、André Loupy、Alain Petit、Boujemâa Daou、Mohamed Soufiaoui

  DOI：10.1016/s0040-4020(00)00992-3

  日期：2001.1

  Cyclocondensation of N-(carbotrifluoromethyl)-ortho-arylenediamines leads to a series of 2-trifluoromethylarylimidazoles with good yields on montmorillonite K10 in ‘dry media’ under microwave irradiation within 2 min in a domestic oven. By conventional heating in the same conditions, no reaction is observed.

  的环化缩合ñ - （carbotrifluoromethyl） -邻-arylenediamines导致对蒙脱土K10在“干媒体”在2分钟内在家用烤箱一系列2-trifluoromethylarylimidazoles具有良好产率微波辐射下。在相同条件下通过常规加热，未观察到反应。
• Method of inhibiting neoplastic cells with benzimidazole derivatives
  申请人：——

  公开号：US20020082280A1

  公开（公告）日：2002-06-27

  A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to benzimidazole derivatives.

  一种通过将受影响的细胞暴露于苯并咪唑衍生物来抑制肿瘤，特别是癌症和癌前病变的方法。