4-methyl-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline | 19848-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline
• 英文别名: 4-Methyl-1-phenyl-s-triazolo<4,3-a>chinoxalin；1-Phenyl-4-methyl-1,2,4-triazolo<4,3-a>chinoxalin；1-phenyl-4-methyl-1,2,4-triazolo[4,3-a]quinoxaline；4-Methyl-1-phenyl(1,2,4)triazolo(4,3-a)quinoxaline
• CAS: 19848-92-1
• 化学式: C₁₆H₁₂N₄
• 分子量: 260.298
• InChiKey: WBEHLJGGQKPBGY-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-3-甲基喹喔啉 在 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 4-methyl-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline
  参考文献：
  名称：

  [EN] TRIAZOLOPYRAZINE DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL AND PSYCHIATRIC DISORDERS
  [FR] DÉRIVÉS DE TRIAZOLOPYRAZINE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET PSYCHIATRIQUES

  摘要：

  本发明涉及式(I)的三唑吡嗪化合物。该发明的不同方面涉及包含所述化合物的药物组合物以及将该化合物用作治疗神经系统和精神疾病的治疗剂的用途。

  公开号：

  WO2013034755A1

文献信息

• [EN] TRIAZOLOPYRAZINE DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL AND PSYCHIATRIC DISORDERS<br/>[FR] DÉRIVÉS DE TRIAZOLOPYRAZINE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET PSYCHIATRIQUES
  申请人：LUNDBECK & CO AS H

  公开号：WO2013034755A1

  公开（公告）日：2013-03-14

  The present invention is directed to triazolopyrazine compounds of Formula (I). Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds as therapeutic agents treating neurological and psychiatric disorders.

  本发明涉及式(I)的三唑吡嗪化合物。该发明的不同方面涉及包含所述化合物的药物组合物以及将该化合物用作治疗神经系统和精神疾病的治疗剂的用途。
• Hypervalent Iodine‐Mediated Synthesis of 1‐Aryl‐4‐methyl‐1,2,4‐triazolo[4,3‐a]quinoxalines by Oxidative Cyclization of Arene Carbaldehyde‐3‐methylquinoxalin‐2‐yl Hydrazones
  作者：Ranjana Aggarwal、Garima Sumran

  DOI：10.1080/00397910600602586

  日期：2006.7

  Abstract Arene carbaldehyde‐3‐methylquinoxalin‐2‐yl hydrazones (2) obtained by the condensation of 2‐hydrazino‐3‐methylquinoxaline (1) with various aromatic aldehydes, on treatment with iodobenzene diacetate (IBD) in dichloromethane, undergo oxidative cyclization to exclusively afford 1‐aryl‐4‐methyl‐1,2,4‐triazolo[4,3‐a]quinoxalines (5) in excellent yield.

  摘要 芳烃甲醛-3-甲基喹喔啉-2-基腙(2) 由2-肼基-3-甲基喹喔啉(1) 与各种芳香醛缩合得到，在二氯甲烷中用碘苯二乙酸酯(IBD) 处理，经过氧化环化得到以优异的收率独家提供 1-芳基-4-甲基-1,2,4-三唑并[4,3-a]喹喔啉 (5)。
• Synthesis of Triazoloquinoxalines as Antitubercular Agents
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Vajja Sambasiva Rao、Dalip Kumar

  DOI：10.5012/bkcs.2011.32.8.2657

  日期：2011.8.20

  1,2,4-Triazoles and quinoxalines were found to display various pharmacological activities. Hence a series of 1-aryl-4-methyl-1,2,4-triazolo[4,3-a]quinoxalines were synthesized. Due to various advantages of organic reactions under solvent-free conditions these compounds were developed using iodobenzene diacetate under solvent-free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, $^1H$ NMR, $^13}C$ NMR and HRMS. All the synthesized compounds were investigated for their antitubercular activity and 5g was found to the most active compound.

  研究发现，1,2,4-三唑和喹喔啉类化合物具有多种药理活性。因此，我们合成了一系列 1-芳基-4-甲基-1,2,4-三唑并[4,3-a]喹喔啉类化合物。由于在无溶剂条件下进行有机反应具有各种优势，因此这些化合物是在无溶剂条件下使用二乙酸碘苯进行合成的。合成的化合物通过元素显微分析、红外光谱、$^1H$ NMR、$^13}C$ NMR 和 HRMS 进行了表征。研究了所有合成化合物的抗结核活性，发现 5g 是活性最高的化合物。
• Some novel observations on the reaction of 2-hydrazino-3-methylquinoxaline with trifluoromethyl-β-diketones
  作者：Ranjana Aggarwal、Rajiv Kumar、Shiv P. Singh

  DOI：10.1016/j.jfluchem.2009.06.021

  日期：2009.10

  The reaction of 2-hydrazino-3-methylquinoxaline 1 with trifluoromethyl-beta-diketones 2 not only yields the expected 5-trifluoromethyl-5-hydroxy-Delta(2)-pyrazolines 3a-3f and/or 3-trifluoromethylpyrazoles 4c-4f but also the unexpected products 1,2,4-triazolo[4,3-a]quinoxalines 5a-5f and/or 3(5)-trifluoromethyl-1H-pyrazoles 6c-6f. Furthermore, the acid-catalyzed dehydration of 5-hydroxypyrazolines 3a-3b resulted in the formation of unexpected 5a-5b along with the expected corresponding pyrazoles 7a-7b. These unprecedented observations provide evidence for the existence of equilibrium between the hydroxypyrazoline 3 and its open chain tautomer, ketoimine 9 in the mechanistic path leading to the formation of pyrazoles 7 and triazoles 5. (C) 2009 Elsevier B.V. All rights reserved.
• 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES
  申请人：Andrés-Gil José Ignacio

  公开号：US20140147386A1

  公开（公告）日：2014-05-29

  The present invention relates to novel 1-aryl-4-methyl-[1,2,4]triazolo[4,3-a]-quinoxaline derivatives as inhibitors of phosphodiesterase 2 (PDE2) and to a lesser extent of phosphodiesterase 10 (PDE10) or as inhibitors of both, phosphodiesterases 2 and 10. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which PDE2 is involved, or disorders in which both PDE2 and PDE 10 are involved, such as neurological and psychiatric disorders, and endocrinological or metabolic diseases. The present invention also relates to radiolabelled compounds which may be useful for imaging and quantifying the PDE2 enzyme in tissues, using positron-emission tomography (PET). The invention is also directed to compositions comprising such compounds, to processes for preparing such compounds and compositions, to the use of such compounds and compositions for imaging a tissue, cells or a host, in vitro or in vivo and to precursors of said compounds.

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