2-甲基-1H-苯并咪唑-5-羧酸乙酯 | 717-37-3

• 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-甲基-1H-苯并咪唑-5-羧酸乙酯
• 英文名称: 5-ethoxycarbonyl-2-methylbenzimidazole
• 英文别名: 2-Methyl-5-ethoxycarbonyl-benzimidazol；ethyl 2-methyl-1H-benzimidazole-5-carboxylate；2-methyl-1(3)H-benzoimidazole-5-carboxylic acid ethyl ester；2-methyl-1(3)H-benzimidazole-5-carboxylic acid ethyl ester；2-Methyl-1(3)H-benzimidazol-5-carbonsaeure-aethylester；2-Methyl-1H-benzimidazole-5-carboxylic acid ethyl ester；ethyl 2-methyl-3H-benzimidazole-5-carboxylate
• CAS: 717-37-3
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD09027456
• 分子量: 204.228
• InChiKey: HVEHULVPFMWQAB-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  410.1±18.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-1H-苯并咪唑-5-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 以21%的产率得到(2-甲基-1H-苯并咪唑-5-基)甲醇
  参考文献：
  名称：

  [EN] OGA INHIBITOR COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS D'OGA

  摘要：

  本发明涉及O-GlcNAc水解酶（OGA）抑制剂。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物和组合物预防和治疗抑制OGA有益的疾病的用途，例如tau病变，特别是阿尔茨海默病或进行性上行性麻痹; 以及伴有tau病理的神经退行性疾病，特别是由C90RF72突变引起的肌萎缩性侧索硬化或额颞叶痴呆。

  公开号：

  WO2019243528A1
• 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 2-甲基-1H-苯并咪唑-5-羧酸乙酯
  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。
• Method of inhibiting neoplastic cells with benzimidazole derivatives
  申请人：Cell Pathways, Inc.

  公开号：US06348032B1

  公开（公告）日：2002-02-19

  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。
• 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。
• Nouvelle voie de synthèse des arylimidazoles sous irradiation micro-ondes en “milieu sec”
  作者：Khalid Bougrin、Mohamed Soufiaoui

  DOI：10.1016/0040-4039(95)00611-f

  日期：1995.5

  Arylimidazoles are prepared in good yields on solid mineral supports in “dry media” and under microwave irradiation in domestic ovens.

  在“干介质”中以及在家用烤箱中的微波辐射下，在固态矿物载体上以高收率制备丙烯酸咪唑。
• New transition metal ion complexes with benzimidazole-5-carboxylic acid hydrazides with antitumor activity
  作者：Shadia A. Galal、Khaled H. Hegab、Ahmed S. Kassab、Mireya L. Rodriguez、Sean M. Kerwin、Abdel-Mo'men A. El-Khamry、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2008.07.013

  日期：2009.4

  Metal complexes of 2-methyl-1H-benzimidazole-5-carboxylic acid hydrazide (4a; L1) and its Schiff base 2-methyl-N-(propan-2-ylidene)-1H-benzimidazole-5-carbohydrazide (5a; L2) with transition metal ions e.g., copper, silver, nickel, iron and manganese were prepared. The complexes formed were 1:1 or 1:2 M:L complexes and have the structural formulae [Cu(L1)Cl(H2O)]Cl·3H2O (6), [Ag(L1)NO3(H2O)] (7),

  2-甲基-1 H-苯并咪唑-5-羧酸酰肼的金属配合物（4a ; L 1）及其席夫碱2-甲基-N-（丙烷-2-亚烷基）-1 H-苯并咪唑-5-碳酰肼（制备具有过渡金属离子例如铜，银，镍，铁和锰的5a； L 2）。形成的配合物为1：1或1：2 M：L配合物，并具有结构式[Cu（L 1）Cl（H 2 O）] Cl·3H 2 O（6），[Ag（L 1）NO 3（H 2 O）]（7），[Ni（L 1）Cl 2（H 2 O）2 ]·H 2 O（8），[Fe（L 1）Cl 3（H 2 O）]·3H 2 O（9）和[Mn（L 1）2 Cl（H 2 O）用于配体L 1的] Cl·3H 2 O（10）和[Cu（L 2）Cl 2（H 2 O）2 ]·H 2 O（11），[Ag（L 2）2 ] NO 3 ·H 2 O（12），[Ni（L 2）2 Cl 2 ]·5H 2 O（13），[Fe（L 2）2 Cl 2 ]