1H-吡唑-4-羧酸,3-(乙酰基氨基)-,乙基酯 | 15250-36-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1H-吡唑-4-羧酸,3-(乙酰基氨基)-,乙基酯
• 英文名称: ethyl 3-acetamido-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 5-acetamido-1H-pyrazole-4-carboxylate
• CAS: 15250-36-9
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: VXPNQAVZOJQXJV-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  478.7±30.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H-吡唑-4-羧酸,3-(乙酰基氨基)-,乙基酯 在 溴 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以90%的产率得到5-乙酰氨基-3-溴-1H-吡唑-4-羧酸乙酯
  参考文献：
  名称：

  (Pd/C-mediated)coupling–iodocyclization–coupling strategy in discovery of novel PDE4 inhibitors: a new synthesis of pyrazolopyrimidines

  摘要：

  与吡唑并嘧啶部分融合的吡喃酮通过区域选择性构建吡喃酮环的方法制备，采用了（Pd/C介导的）偶联-碘环化反应，之后进行Sonogashira/Heck/Suzuki反应。所需的基于吡唑并嘧啶的反应物通过一种新的H3PO3介导的缩合反应获得。这一策略导致了新型且潜在安全的PDE4抑制剂的发现。

  DOI：

  10.1039/c2md00273f
• 作为产物：
  描述：

  2-氰基-3-乙氧基丙烯酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 1H-吡唑-4-羧酸,3-(乙酰基氨基)-,乙基酯
  参考文献：
  名称：

  Application of Ullmann and Ullmann–Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation

  摘要：

  Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT, receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.056

文献信息

• [EN] BRUTON'S TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：PFIZER

  公开号：WO2014068527A1

  公开（公告）日：2014-05-08

  Disclosed herein are compounds that form covalent bonds with Bruton's tyrosine kinase (BTK). Methods for the preparation of the compounds are disclosed. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the BTK inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions. (Formula I)

  本文披露了一种与Bruton's酪氨酸激酶（BTK）形成共价键的化合物。公开了制备这些化合物的方法。还披露了包括这些化合物的药物组合物。公开了使用BTK抑制剂的方法，单独或与其他治疗剂联合治疗自身免疫疾病或症状、异源免疫疾病或症状、癌症，包括淋巴瘤，以及炎症性疾病或症状的方法。 (化学式I)
• [EN] N-((HET)ARYLMETHYL)-HETEROARYL-CARBOXAMIDES COMPOUNDS AS PLASMA KALLIKREIN INHIBITORS,<br/>[FR] COMPOSÉS N-((HET)ARYLMÉTHYL)-HÉTÉROARYL-CARBOXAMIDES COMME INHIBITEURS DE LA KALLIKRÉINE PLASMATIQUE
  申请人：KALVISTA PHARMACEUTICALS LTD

  公开号：WO2016083820A1

  公开（公告）日：2016-06-02

  The present invention provides compounds of formula (I): (I) compositions comprising such compounds; the use of such compounds in therapy (for example in the treatment or prevention of a disease or condition in which plasma kallikrein activity is implicated); and methods of treating patients with such compounds; wherein R5, R6, R7, A, B, W, X, Y and Z are as defined herein.

  本发明提供了以下公式(I)的化合物：(I)包含这种化合物的组合物；在治疗中使用这种化合物（例如在涉及血浆卡利克雷因活性的疾病或病况的治疗或预防中）；以及使用这种化合物治疗患者的方法；其中R5、R6、R7、A、B、W、X、Y和Z的定义如本文所述。
• [EN] PYRAZOLE DERIVATIVES AS PLASMA KALLIKREIN INHIBITORS<br/>[FR] DÉRIVÉS DE PYRAZOLE EN TANT QU'INHIBITEURS DE LA KALLICRÉINE PLASMATIQUE
  申请人：KALVISTA PHARMACEUTICALS LTD

  公开号：WO2017207983A1

  公开（公告）日：2017-12-07

  The present invention provides a selection of compounds of formula (I): (I) compositions comprising such compounds; the use of such compounds in therapy (for example in the treatment or prevention of a disease or condition in which plasma kallikrein activity is implicated); and methods of treating patients with such compounds; wherein R5,R6,R7, A, B,W, X, Y and Z are as defined herein.

  本发明提供了一种化合物选择，其化学式为（I）：（I）包含这种化合物的组合物；在治疗中使用这种化合物（例如在涉及血浆激肽酶活性的疾病或病况的治疗或预防中）；以及使用这种化合物治疗患者的方法；其中R5、R6、R7、A、B、W、X、Y和Z的定义如本文所述。
• (Pd/C-mediated)coupling–iodocyclization–coupling strategy in discovery of novel PDE4 inhibitors: a new synthesis of pyrazolopyrimidines
  作者：P. Mahesh Kumar、K. Siva Kumar、Chandana L. T. Meda、G. Rajeshwar Reddy、Pradeep K. Mohakhud、K. Mukkanti、G. Rama Krishna、C. Malla Reddy、D. Rambabu、K. Shiva Kumar、K. Krishna Priya、Keerthana Sarma Chennubhotla、Rakesh Kumar Banote、Pushkar Kulkarni、Kishore V. L. Parsa、Manojit Pal

  DOI：10.1039/c2md00273f

  日期：——

  Pyranones fused with a pyrazolopyrimidine moiety were prepared via regioselective construction of pyranone ring using (Pd/C-mediated)coupling–iodocyclization followed by Sonogashira/Heck/Suzuki reactions. The pyrazolopyrimidine based reactant required was obtained via a new H3PO3 mediated condensation reaction. This strategy has led to the discovery of a novel and potentially safe PDE4 inhibitor.

  与吡唑并嘧啶部分融合的吡喃酮通过区域选择性构建吡喃酮环的方法制备，采用了（Pd/C介导的）偶联-碘环化反应，之后进行Sonogashira/Heck/Suzuki反应。所需的基于吡唑并嘧啶的反应物通过一种新的H3PO3介导的缩合反应获得。这一策略导致了新型且潜在安全的PDE4抑制剂的发现。
• [EN] PI3 KINASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PI3 KINASE ET LEURS UTILISATIONS
  申请人：FRONTHERA U S PHARMACEUTICALS LLC

  公开号：WO2019028395A1

  公开（公告）日：2019-02-07

  Described herein are PI3 Kinase inhibitors and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of cancer, cardiovascular diseases, and inflammatory diseases.

  本文介绍了PI3激酶抑制剂和含有该化合物的药物组合物。这些化合物和组合物对于治疗癌症、心血管疾病和炎症性疾病非常有用。