3-Methyl-7-trifluoromethylquinoxaline-2(1H)-one | 166402-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Methyl-7-trifluoromethylquinoxaline-2(1H)-one
• 英文别名: 3-methyl-7-trifluoromethyl-1H-quinoxalin-2-one；3-methyl-7-(trifluoromethyl)-1H-quinoxalin-2-one
• CAS: 166402-52-4
• 化学式: C₁₀H₇F₃N₂O
• 分子量: 228.174
• InChiKey: QVBCXXWMNSIAGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Methyl-7-trifluoromethylquinoxaline-2(1H)-one 在 三氯氧磷 作用下， 反应 2.0h， 以77%的产率得到2-Chloro-3-methyl-7-trifluoromethylquinoxaline
  参考文献：
  名称：

  Loriga; Fiore; Sanna, Il Farmaco, 1995, vol. 50, # 5, p. 289 - 301

  摘要：

  DOI：
• 作为产物：
  描述：

  N-<(2-Nitro-4-trifluoromethyl)phenyl>alanine 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 双氧水 作用下， 以 乙醇 为溶剂， 15.0~100.0 ℃ 、303.98 kPa 条件下， 反应 1.33h， 生成 3-Methyl-7-trifluoromethylquinoxaline-2(1H)-one
  参考文献：
  名称：

  Loriga; Fiore; Sanna, Il Farmaco, 1995, vol. 50, # 5, p. 289 - 301

  摘要：

  DOI：

文献信息

• Quinoxaline‐based efflux pump inhibitors restore drug susceptibility in drug‐resistant nontuberculous mycobacteria
  作者：Paola Corona、Roberta Ibba、Sandra Piras、Paola Molicotti、Alessandra Bua、Antonio Carta

  DOI：10.1002/ardp.202100492

  日期：2022.8

  abscessus. The two NTMs were tested for drug susceptibility against different antibiotics. To restore drug susceptibility, a new series of 2-aryl-3-phenoxymethyl-quinoxaline derivatives (QXs) was designed, synthesized, and investigated as efflux pump inhibitors (EPIs) against two clinical isolates of the above-cited NTMs, evaluating how EPIs can influence the drug minimal inhibitory concentration values

  非结核分枝杆菌 (NTM) 包括几种普遍存在的环境局部细菌，这些细菌可能导致严重的人类疾病。NTM 相关肺部感染主要影响患有潜在呼吸道疾病或慢性疾病的个体和免疫抑制患者。模拟分枝杆菌和脓肿分枝杆菌是导致免疫功能正常和免疫功能低下个体肺部疾病的两种 NTM。在这项研究中，从意大利一家医院收治的两名患者身上分离出两种 NTM 菌株，分别被鉴定为M. simiae和M. abscessus. 测试了两种 NTM 对不同抗生素的药物敏感性。为了恢复药物敏感性，设计、合成了一系列新的 2-aryl-3-phenoxymethyl-quinoxaline 衍生物 (QX)，并将其作为外排泵抑制剂 (EPI) 对上述 NTM 的两种临床分离株进行研究，评估 EPI 如何可以影响药物的最小抑制浓度值，从而影响活性。在临床菌株中追踪的不同耐药水平被 EPI 降低，并且在一些情况下，易感性完全恢复。QX 还可
• Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted-3-Methyl-Quinoxalin-2-Ones with<scp><i>N</i></scp>-Phenylglycine
  作者：Julio R. De la Fuente、Álvaro Cañete、Carolina Jullian、Claudio Saitz、Christian Aliaga

  DOI：10.1111/php.12162

  日期：2013.11

  AbstractPhotoinduced electron transfer between N‐phenylglycine (NPG) and electronically excited triplets of 7‐substituted‐3‐methyl‐quinoxalin‐2‐ones in acetonitrile generate the respective ion radical pair, where by decarboxylation the phenyl‐amino‐alkyl radical, PhNHCH2•, is generated. This radical reacts with the 3‐methyl‐quinoxalin‐2‐ones ground states, leading to the product 2. Other, unexpected, 7‐substituted‐1,2,3,3a‐tetrahydro‐3a‐methyl‐2‐phenylimidazo[1,5‐a]quinoxalin‐4(5H)‐ones, annulation products, 3a–f, were generated; likely by the addition of two PhNHCH2• radicals, to positions 3 and 4 of the quinoxalin‐2‐ones. The reaction mechanism includes a photoinduced one electron transfer initiation step, propagation steps involving radical intermediates and NPG with radical chain termination steps that lead to the respective products 2a–f and 3a–f and NPG by‐products. The proposed mechanism accounts for the strong dependency found for the initial photoconsumption quantum yields on the electron‐withdrawing power of the substituent. Therefore, photolysis of common reactants widely used such as NPG and substituted quinoxalin‐2‐ones may provide a simple synthetic way to the unusual, unreported tetrahydro‐imidazoquinoxalinones 3a–f.
• Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2
  作者：Paolo Sanna、Antonio Carta、Mario Loriga、Stefania Zanetti、Leonardo Sechi

  DOI：10.1016/s0014-827x(99)00010-5

  日期：1999.3

  A new set of 35 3-alkyl and 3-ethoxycarbonylalkyl 6- and/or 7-substituted-2-quinoxalinones was prepared and submitted to a preliminary in vitro investigation of their antimicrobial, anticancer and anti-HIV activities. Results are referred. (C) 1999 Elsevier Science S.A. All rights reserved.