methyl 1-benzyl-2-oxo-3H-benzimidazole-5-carboxylate | 214903-69-2

• 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: methyl 1-benzyl-2-oxo-3H-benzimidazole-5-carboxylate
• CAS: 214903-69-2
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: SQZHYOUVAHDLSH-UHFFFAOYSA-N

物化性质

• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-2-oxo-3H-benzimidazole-5-carboxylate 在 盐酸 、 三氯氧磷 作用下， 反应 4.0h， 以68.6%的产率得到1-苄基-2-氯-1H-苯并咪唑-5-羧酸甲酯
  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：

  methyl 4-(benzylamino)-3-nitrobenzoate 在 nickel dichloride 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 methyl 1-benzyl-2-oxo-3H-benzimidazole-5-carboxylate
  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

文献信息

• [EN] GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT<br/>[FR] AGONISTE DU RÉCEPTEUR GPR40, PROCÉDÉS DE PRÉPARATION DE CELUI-CI, ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CELUI-CI EN TANT QUE SUBSTANCE ACTIVE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2014073904A1

  公开（公告）日：2014-05-15

  The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

  本发明涉及一种具有GPR40受体激动剂活性的新化合物，可促进胰岛素分泌并抑制葡萄糖负荷后血糖升高，因此适用于糖尿病及其并发症的治疗，以及包含它们作为活性成分的制备方法和药物组合物。
• GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE AGENT
  申请人：LG LIFE SCIENCES LTD.

  公开号：US20150291584A1

  公开（公告）日：2015-10-15

  The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

  本发明涉及一种新型化合物，具有GPR40受体激动剂活性，促进胰岛素分泌并抑制葡萄糖负荷后血糖升高，因此可用于糖尿病及其并发症的治疗，其制备方法和含有其作为活性成分的药物组合物。
• Synthesis and bioevaluation of pyrazole-benzimidazolone hybrids as novel human 4-Hydroxyphenylpyruvate dioxygenase inhibitors
  作者：Yu-Ling Xu、Hong-Yan Lin、Xu Ruan、Sheng-Gang Yang、Ge-Fei Hao、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.ejmech.2015.01.018

  日期：2015.3

  4-Hydroxyphenylpyruvate dioxygenase (HPPD), an essential enzyme in tyrosine catabolism, is an important target for treating type I tyrosinemia. Inhibition of HPPD can effectively alleviate the symptoms of type I tyrosinemia. However, only one commercial HPPD inhibitor, 2-(2-nitro-4-trifluoromethylbenzoyl) cyclohexane-1,3-dione (NTBC), has been available for clinical use so far. In the present study, a series of novel pyrazole-benzimidazolone hybrids were designed, synthesized and evaluated as potent human HPPD inhibitors. Most of the new compounds displayed significant inhibitory activity against the recombinant human HPPD. Moreover, compound 91 was identified as the most potent candidate with IC50 value of 0.021 mu M against recombinant human HPPD, about 3-fold more potent than NTBC. Thus the pyrazole-benzimidazolone hybrid has great potential to be further developed for the treatment of type I tyrosinemia. (C) 2015 Elsevier Masson SAS. All rights reserved.
• GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：LG Life Sciences Ltd.

  公开号：EP2917180A1

  公开（公告）日：2015-09-16
• US9988379B2
  申请人：——

  公开号：US9988379B2

  公开（公告）日：2018-06-05