ethyl 1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylate | 1198352-87-2

• 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 1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylate
• 英文别名: Ethyl 1-(5-chloro-2-methoxyphenyl)-5-methylpyrazole-4-carboxylate
• CAS: 1198352-87-2
• 化学式: C₁₄H₁₅ClN₂O₃
• 分子量: 294.738
• InChiKey: LZARYFMMLFCAIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以90%的产率得到1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carbohydrazide
  参考文献：
  名称：

  Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles

  摘要：

  In the present investigation a series of novel 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-IH-pyrazol-4yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles (4a-j) were synthesized by cyclization of substituted-benzoic acid N'-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-hydrazide by using phosphorousoxychloride at 120 degrees C. The chemical structure of the newly synthesized compounds was 13 characterized by analytical and spectral (IR, H-1 NMR, C-13 NMR and LC-MS) methods. The title compounds were screened for qualitative (zone of inhibition) and quantitative antibacterial activity (MIC) by agar cup plate and microtitration methods, respectively. Among the synthesized compounds in this series compound 2-[1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl-5-(4-fluorophenyl)-1,3,4-oxadiazole (4b) was found to exhibit significant antibacterial activity with MICs of 22.4, 29.8, 29.6 and 30.0 mu g/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively. The other compounds exhibited moderate activity when compared to standard substance Ampicillin. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.020
• 作为产物：
  描述：

  ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 、 (5-氯-2-甲氧基苯基)-肼盐酸盐 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以70%的产率得到ethyl 1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles

  摘要：

  In the present investigation a series of novel 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-IH-pyrazol-4yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles (4a-j) were synthesized by cyclization of substituted-benzoic acid N'-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-hydrazide by using phosphorousoxychloride at 120 degrees C. The chemical structure of the newly synthesized compounds was 13 characterized by analytical and spectral (IR, H-1 NMR, C-13 NMR and LC-MS) methods. The title compounds were screened for qualitative (zone of inhibition) and quantitative antibacterial activity (MIC) by agar cup plate and microtitration methods, respectively. Among the synthesized compounds in this series compound 2-[1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl-5-(4-fluorophenyl)-1,3,4-oxadiazole (4b) was found to exhibit significant antibacterial activity with MICs of 22.4, 29.8, 29.6 and 30.0 mu g/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively. The other compounds exhibited moderate activity when compared to standard substance Ampicillin. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.020

文献信息

• [EN] NOVEL MACROCYCLES AS FACTOR XIA INHIBITORS<br/>[FR] NOUVEAUX MACROCYCLES EN TANT QU'INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013022818A1

  公开（公告）日：2013-02-14

  The present invention provides compounds of Formula (Ia): or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein all the variables are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of FXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供了化合物的公式(Ia)：或其立体异构体、互变异构体或药用可接受盐，其中所有变量如本文所定义。这些化合物是选择性因子XIa抑制剂或FXIa和血浆激肽原的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗血栓栓塞和/或炎症性疾病的方法。
• NOVEL MACROCYCLES AS FACTOR XIA INHIBITORS
  申请人：Pinto Donald J. P.

  公开号：US20140221338A1

  公开（公告）日：2014-08-07

  The present invention provides compounds of Formula (Ia): or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein all the variables are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of FXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供以下式（Ia）的化合物：或其立体异构体、互变异构体或药学上可接受的盐，其中所有变量均如本文所定义。这些化合物是选择性因子XIa抑制剂或FXIa和血浆卡利肌酶的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗血栓栓塞性和/或炎症性疾病的方法。
• Macrocycles as factor XIa inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10208068B2

  公开（公告）日：2019-02-19

  The present invention provides compounds of Formula (Ia): or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein all the variables are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of FXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供了式 (Ia) 的化合物： 或其立体异构体、同系物或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性因子 XIa 抑制剂或 FXIa 和血浆钙激酶的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些化合物治疗血栓栓塞性和/或炎症性疾病的方法。
• US9221818B2
  申请人：——

  公开号：US9221818B2

  公开（公告）日：2015-12-29
• US9611274B2
  申请人：——

  公开号：US9611274B2

  公开（公告）日：2017-04-04