1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methyl Ester | 219325-02-7

• 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: 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methyl Ester
• 英文别名: Methyl 1,3-diethyl-2-oxobenzimidazole-5-carboxylate
• CAS: 219325-02-7
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: JPIPOZQUWPCIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methyl Ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 1,3-diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and bioevaluation of pyrazole-benzimidazolone hybrids as novel human 4-Hydroxyphenylpyruvate dioxygenase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.01.018
• 作为产物：
  描述：

  2-氧代-2,3-二氢-1H-1,3-苯并咪唑-5-羧酸甲酯 在 碘乙烷 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 1.0h， 生成 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methyl Ester
  参考文献：
  名称：

  [EN] METHODS OF TREATING ACUTE INFLAMMATION IN ANIMALS WITH p38 MAP KINASE INHIBITORS
  [FR] METHODES DE TRAITEMENT DE L'INFLAMMATION AIGUE CHEZ LES ANIMAUX AVEC DES INHIBITEURS DE LA PROTEINE KINASE MAP P38

  摘要：

  本发明提供了治疗患有急性炎症状况的动物（包括乳腺炎）的方法，通过给予至少一种p38 MAP激酶抑制剂。本发明还提供了一种方法，通过给予至少一种p38 MAP激酶抑制剂，来增强患有急性炎症状况的动物的乳制品产量并减少废弃的乳制品。

  公开号：

  WO2005060967A1

文献信息

• Novel benzimidazole anti-inflammatory compounds
  申请人：Pfizer Inc.

  公开号：US20030092749A1

  公开（公告）日：2003-05-15

  The present invention relates to novel triazolo-pyridines of the formula I 1 wherein Het is an optionally substituted 5 -membered heterocycle containing one to two heteroatoms selected from nitrogen, sulfur and oxygen wherein at least one of said heteroatoms atoms must be nitrogen; R 2 is selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl or other suitable substituents; R 3 is selected from the group consisting of hydrogen, (C 1 -C6)alkyl or other suitable substituents; s is an integer from 0-5; to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, repurfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明涉及公式I的新型三唑基吡啶 其中Het是一个可选择取代的 含有一个到两个氮、硫和氧杂原子的5元杂环，其中至少一个杂原子必须是氮; R 2 选自由氢、(C 1 -C 6 )烷基或其他适当的取代基组成的群; R 3 选自由氢、(C 1 -C6)烷基或其他适当的取代基组成的群; s是0-5之间的整数; 用于它们的制备的中间体，含有它们的药物组合物以及它们的药用。本发明的化合物是MAP激酶，优选为p38激酶的有效抑制剂。它们在治疗炎症、骨关节炎、类风湿性关节炎、癌症、中风或心脏病发中的再灌注或缺血、自身免疫疾病和其他疾病中有用。
• US7056918B2
  申请人：——

  公开号：US7056918B2

  公开（公告）日：2006-06-06
• 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.
• [EN] METHODS OF TREATING ACUTE INFLAMMATION IN ANIMALS WITH p38 MAP KINASE INHIBITORS<br/>[FR] METHODES DE TRAITEMENT DE L'INFLAMMATION AIGUE CHEZ LES ANIMAUX AVEC DES INHIBITEURS DE LA PROTEINE KINASE MAP P38
  申请人：PFIZER PROD INC

  公开号：WO2005060967A1

  公开（公告）日：2005-07-07

  The present invention provides methods for treating animals having acute inflammatory conditions, including mastitis, by administering at least one p38 MAP kinase inhibitor. The present invention also provides methods for enhancing milk production and reducing milk discard in animals afflicted with acute inflammatory conditions by administering at least one, p38 MAP kinase inhibitor.

  本发明提供了治疗患有急性炎症状况的动物（包括乳腺炎）的方法，通过给予至少一种p38 MAP激酶抑制剂。本发明还提供了一种方法，通过给予至少一种p38 MAP激酶抑制剂，来增强患有急性炎症状况的动物的乳制品产量并减少废弃的乳制品。