ethyl 5-(2-bromoacetyl)-1-methyl-1H-pyrazole-3-carboxylate | 1227409-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(2-bromoacetyl)-1-methyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 5-(2-bromoacetyl)-1-methyl-1H-pyrazol-3-carboxylate；Ethyl 5-(2-bromoacetyl)-1-methylpyrazole-3-carboxylate；ethyl 5-(2-bromoacetyl)-1-methylpyrazole-3-carboxylate
• CAS: 1227409-99-5
• 化学式: C₉H₁₁BrN₂O₃
• 分子量: 275.102
• InChiKey: MEQXAPXLCCHUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-bromoacetyl)-1-methyl-1H-pyrazole-3-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1-methyl-5-(2-(p-tolylamino)thiazol-4-yl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.

  DOI：

  10.1021/acs.jmedchem.7b00793
• 作为产物：
  描述：

  5-乙酰基1H-吡唑-3-羧酸乙酯 在 苯基三甲基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 ethyl 5-(2-bromoacetyl)-1-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  NOVEL PYRAZOLE-3-CARBOXAMIDE DERIVATIVE HAVING 5-HT2B RECEPTOR ANTAGONIST ACTIVITY

  摘要：

  揭示的是由通式（I）表示的化合物或其药用可接受盐，其作为5-HT2B受体的选择性拮抗剂是有用的。该化合物和盐可用于治疗或预防与5-HT2B受体相关的各种疾病和症状。

  公开号：

  US20110275628A1

文献信息

• NOVEL PYRAZOLE-3-CARBOXAMIDE DERIVATE HAVING 5-HT2B RECEPTOR ANTAGONIST ACTIVITY
  申请人：RaQualia Pharma Inc

  公开号：EP2386546A1

  公开（公告）日：2011-11-16

  Disclosed is a compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, which is useful as a selective antagonist of a 5-HT2B receptor. The compound and salt are useful for treatment or prevention of various diseases and conditions associated with a 5-HT2B receptor.

  本发明公开了通式 (I) 所代表的化合物或其药学上可接受的盐，可用作 5-HT2B 受体的选择性拮抗剂。该化合物和盐可用于治疗或预防与 5-HT2B 受体相关的各种疾病和病症。
• US8252790B2
  申请人：——

  公开号：US8252790B2

  公开（公告）日：2012-08-28
• NOVEL PYRAZOLE-3-CARBOXAMIDE DERIVATIVE HAVING 5-HT2B RECEPTOR ANTAGONIST ACTIVITY
  申请人：Yamagishi Tatsuya

  公开号：US20110275628A1

  公开（公告）日：2011-11-10

  Disclosed is a compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, which is useful as a selective antagonist of a 5-HT 2B receptor. The compound and salt are useful for treatment or prevention of various diseases and conditions associated with a 5-HT 2B receptor.

  揭示的是由通式（I）表示的化合物或其药用可接受盐，其作为5-HT2B受体的选择性拮抗剂是有用的。该化合物和盐可用于治疗或预防与5-HT2B受体相关的各种疾病和症状。
• Substituted <i>N</i>-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery
  作者：Elisa Azzali、Diana Machado、Amit Kaushik、Federica Vacondio、Sara Flisi、Clotilde Silvia Cabassi、Gyanu Lamichhane、Miguel Viveiros、Gabriele Costantino、Marco Pieroni

  DOI：10.1021/acs.jmedchem.7b00793

  日期：2017.8.24

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.