2-(3-methyl-1H-pyrazol-5-yl)aniline | 114554-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-methyl-1H-pyrazol-5-yl)aniline
• 英文别名: 2-(5-methyl-1(2)H-pyrazol-3-yl)-aniline；2-(5-Methyl-1(2)H-pyrazol-3-yl)-anilin；2-(5-methyl-1H-pyrazol-3-yl)aniline
• CAS: 114554-23-3
• 化学式: C₁₀H₁₁N₃
• mdl: MFCD17015592
• 分子量: 173.217
• InChiKey: AISXDDNPFKZTJA-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C
• 沸点：
  383.8±27.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methyl-1H-pyrazol-5-yl)aniline 在 水 、 溶剂黄146 、 sodium nitrite 作用下， 生成 2-methyl-benzo[e]pyrazolo[1,5-c][1,2,3]triazine
  参考文献：
  名称：

  Koenigs; v. Loesch, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 59,62

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯乙酮 在 palladium 10% on activated carbon hydrazine hydrate 、 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 3.0h， 生成 2-(3-methyl-1H-pyrazol-5-yl)aniline
  参考文献：
  名称：

  [EN] TRIAZOLO- AND PYRAZOLOQUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITOR
  [FR] DÉRIVÉS DE TRIAZOLO- ET DE PYRAZOLOQUINAZOLINE EN TANT QU'INHIBITEURS D'ENZYME PDE10A

  摘要：

  本发明涉及式(I)化合物的用途，以及它们作为药物成分的应用，特别是用于治疗与中枢神经系统相关的疾病。

  公开号：

  WO2012007006A1

文献信息

• Synthesis and study of the electronic properties of pyrazolo[1,5-c]pyrrolo[1,2-a]quinazoline and pyrazolo[1,5-c]pyrido[1,2-a]quinazoline derivatives
  作者：Paola Acosta、Alejandro Ortiz、Braulio Insuasty、Rodrigo Abonia、Jairo Quiroga

  DOI：10.1007/s00706-016-1783-x

  日期：2017.2

  AbstractNovel pyrazolo[1,5-c]pyrrolo[1,2-a]quinazoline and pyrazolo[1,5-c]pyrido[1,2-a]quinazoline derivatives were prepared by a double cyclization cascade type reaction between 2-(1H-pyrazol-5-yl)anilines and ω-chloroketones using acetic acid both as catalyst and solvent. The electronic and redox properties characterization of the new compounds offers a new alternative in luminescence applications

  AbstractNovel pyrazolo[1,5-c]pyrrolo[1,2-a]quinazoline and pyrazolo[1,5-c]pyrido[1,2-a]quinazoline derivatives were prepared by a double cyclization cascade type reaction between 2-(1H-pyrazol-5-yl)anilines and ω-chloroketones using acetic acid both as catalyst and solvent. The electronic and redox properties characterization of the new compounds offers a new alternative in luminescence applications
• Synthesis and SAR study of new phenylimidazole-pyrazolo[1,5-c]quinazolines as potent phosphodiesterase 10A inhibitors
  作者：Battistina Asproni、Gabriele Murineddu、Amedeo Pau、Gérard A. Pinna、Morten Langgård、Claus Tornby Christoffersen、Jacob Nielsen、Jan Kehler

  DOI：10.1016/j.bmc.2010.10.038

  日期：2011.1

  A series of phenylimidazole-pyrazolo[1,5-c]quinazolines 1a-q was designed, synthesized and characterised as a novel class of potent phophodiesterase 10A (PDE10A) inhibitors. In this series, 2,9-dimethyl-5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)pyrazolo[1,5-c]quinazoline (1q) showed the highest affinity for PDE10A enzyme (IC50 = 16 nM). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of imidazole-4,5- and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus
  作者：Milind Saudi、Joanna Zmurko、Suzanne Kaptein、Jef Rozenski、Johan Neyts、Arthur Van Aerschot

  DOI：10.1016/j.ejmech.2014.09.062

  日期：2014.11

  The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DC5) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 = 1.85 mu M. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 = 0.93 mu M) in Vero cells. (c) 2014 The Authors. Published by Elsevier Masson SAS.
• Saudi, Milind; Zmurko, Joanna; Kaptein, Suzanne, European Journal of Medicinal Chemistry, 2016, vol. 121, p. 158 - 168
  作者：Saudi, Milind、Zmurko, Joanna、Kaptein, Suzanne、Rozenski, Jef、Gadakh, Bharat、Chaltin, Patrick、Marchand, Arnaud、Neyts, Johan、Van Aerschot, Arthur

  DOI：——

  日期：——
• Koenigs; Freund, Chemische Berichte, 1947, vol. 80, p. 143
  作者：Koenigs、Freund

  DOI：——

  日期：——