5-氨基-1-(2-甲基苯基)-1H-吡唑-4-腈 | 142893-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-(2-甲基苯基)-1H-吡唑-4-腈
• 英文名称: (5-amino-1-o-tolyl-1H-pyrazole-4-carbonitrile)
• 英文别名: 5-amino-1-o-tolyl-1H-pyrazole-4-carbonitrile；5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile；5-amino-1-(2-methylphenyl)pyrazole-4-carbonitrile
• CAS: 142893-46-7
• 化学式: C₁₁H₁₀N₄
• mdl: MFCD00128419
• 分子量: 198.227
• InChiKey: DASDHYYNSIACSW-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氨基-1-(2-甲基苯基)-1H-吡唑-4-腈 在 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 4-methanimidoyl-2-(2-methylphenyl)pyrazol-3-amine
  参考文献：
  名称：

  Discovery and Evaluation of 7-Alkyl-1,5-bis-aryl-pyrazolopyridinones as Highly Potent, Selective, and Orally Efficacious Inhibitors of p38α Mitogen-Activated Protein Kinase^⊥⊥ Atomic coordinates and structure factors for crystal structure of compound3dwith p38α can be accessed using PDB code 3LHJ.

  摘要：

  The p38 alpha mitogen-activated protein (MAP) kinase is a central signaling molecule in many proinflammatory pathways, regulating the cellular response to a multitude of external stimuli including heat, ultraviolet radiation, osmotic shock, and a variety of cytokines especially interleukin-1 beta and tumor necrosis factor alpha. Thus, inhibitors of this enzyme are postulated to have significant therapeutic potential for the treatment of rheumatoid arthritis, inflammatory bowel disease, and Crohn's disease, as well as other diseases where aberrant cytokine signaling is the driver of disease. In this communication, we describe a novel class of 7-alkyl-1,5-bis-aryl-pyrazolopyridinone-based p38 alpha inhibitors. In particular, compound 3f is highly potent in the enzyme and cell-based assays, selective in an Ambit kinase screen, and efficacious (ED50 <= 0.01 mg/kg) in the rat collagen induced arthritis (CIA) model.

  DOI：

  10.1021/jm100095x
• 作为产物：
  描述：

  乙氧基亚甲基丙二腈 、 (2-甲基苯基)肼 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 5-氨基-1-(2-甲基苯基)-1H-吡唑-4-腈
  参考文献：
  名称：

  新型GLUT抑制剂的鉴定

  摘要：

  使用HTS将1 H-吡唑并[3,4- d ]嘧啶类化合物鉴定为促进葡萄糖转运蛋白1（GLUT1）的非常有效的抑制剂。建立了分子框架每个环系统的广泛结构-活性关系研究（SAR），揭示了必要的结构动机（即，邻甲氧基取代的苯，哌嗪和嘧啶）。对GLUT2的选择性非常好，并且最初的体外和体内药代动力学（PK）研究令人鼓舞。

  DOI：

  10.1016/j.bmcl.2016.02.050

文献信息

• [EN] PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE SOUS FORME DE PYRAZOLOPYRIMIDINES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004009602A1

  公开（公告）日：2004-01-29

  The present invention relates generally to inhibitors of the kinases and more particularly to novel pyrazolopyrimidine compounds.

  本发明一般涉及激酶的抑制剂，更具体地涉及新型吡唑吡嘧啶化合物。
• 6-Arylmethyl-substituted pyrazolopyrimidines
  申请人：Hendrix Martin

  公开号：US20070161662A1

  公开（公告）日：2007-07-12

  The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

  这项发明涉及新型的6-芳基甲基取代的吡唑吡嘧啶化合物，其制备方法以及它们用于生产用于改善感知、集中力、学习和/或记忆的药物。
• 6-Cyclylmethyl- and 6-alkylmethyl-substituted pyrazolepyrimidines
  申请人：Hendrix Martin

  公开号：US20070105876A1

  公开（公告）日：2007-05-10

  The invention relates to novel 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

  这项发明涉及新颖的6-环己甲基和6-烷基甲基取代的吡唑吡咯嘧啶化合物，其制备方法以及它们用于生产用于改善感知、集中力、学习和/或记忆的药物。
• [EN] COMBINATION THERAPY FOR TREATING MPS1<br/>[FR] POLYTHÉRAPIE POUR LE TRAITEMENT DE LA MPS1
  申请人：GAIN THERAPEUTICS SA

  公开号：WO2021156774A1

  公开（公告）日：2021-08-12

  The application is directed to compounds of formula (I) and their salts and solvates, wherein B, R1, R2, R3, R3', R4, R4', and R5 are as set forth in the specification, as well as to methods for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of, e.g., MPS1, optionally in combination with α-L-iduronidase or an analog or variant thereof, e.g., laronidase.

  该申请涉及公式(I)化合物及其盐和溶剂化合物，其中B、R1、R2、R3、R3'、R4、R4'和R5如规范中所述，以及其制备方法、含有相同化合物的药物组合物，以及用于治疗和/或预防MPS1等疾病的方法，可选地与α-L-异硫酸酶或其类似物或变体（例如，laronidase）结合使用。
• Deacylation during the Synthesis of New 4-Amino-1H-Pyrazolo [3,4-B] Pyridines Catalysed by Sncl₄
  作者：Hua-nan Hu、You Peng、Hua-nan Huang、Tao Yang、Fu-shan Chen、Ping Yan

  DOI：10.3184/174751918x15337230783041

  日期：2018.8

  A series of novel 1-(4-amino-6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-5-yl)-ethanones and 6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-4-amines were prepared by the annulation of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles with acetylacetone in the presence of tin(IV) chloride. The results demonstrated that the ethanones are the precursors of second compounds.

  一系列新型 1-(4-amino-6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-5-yl)-ethoneones 和 6-methyl-1-aryl-1H-pyrazolo[在氯化锡 (IV) 存在下，通过 5-氨基-1-芳基-1H-吡唑-4-腈与乙酰丙酮的环化制备 3,4-b] 吡啶-4-胺。结果表明乙酮是第二化合物的前体。