2,3-Bis-brommethyl-6-methoxychinoxalin | 32602-03-2

• 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: 2,3-Bis-brommethyl-6-methoxychinoxalin
• 英文别名: 2,3-bis(bromomethyl)-6-methoxyquinoxaline；2,3-Bis(bromomethyl)-6-methoxyquinoxaline
• CAS: 32602-03-2
• 化学式: C₁₁H₁₀Br₂N₂O
• 分子量: 346.021
• InChiKey: MXSFZKDGGYWGQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-Bis-brommethyl-6-methoxychinoxalin 在 potassium fluoride 、 18-冠醚-6 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以78%的产率得到2,3-bis(fluoromethyl)-6-methoxyquinoxaline
  参考文献：
  名称：

  Synthesis of 2,3-Bis(halomethyl)quinoxaline Derivatives and Evaluation of Their Antibacterial and Antifungal Activities

  摘要：

  合成了在2位和3位具有双（氟甲基）、双（氯甲基）或双（碘甲基）基团，在6位和/或7位具有各种电子给体/电子受体取代基的喹喔啉衍生物。通过最小抑菌浓度测定法评估了它们的抗菌和抗真菌活性。喹喔啉衍生物的取代基与抗菌活性之间的关系表明，卤甲基单元的电负性在产生抗菌活性方面起着重要作用。

  DOI：

  10.1248/cpb.c12-01061
• 作为产物：
  描述：

  4-甲氧基邻苯二胺 、 1,4-二溴-2,3-丁二酮 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-Bis-brommethyl-6-methoxychinoxalin
  参考文献：
  名称：

  Luminescent bis(benzo[d]thiazolyl)quinoxaline: facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application

  摘要：

  已合成一系列发光的双(苯并[d]噻唑基)喹喔啉化合物，并研究了它们的荧光特性、抗癌效力、与DNA和BSA的相互作用、细胞摄取以及代谢稳定性。

  DOI：

  10.1039/c9ra01498e

文献信息

• Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives
  作者：Hisato Ishikawa、Takayuki Sugiyama、Keisuke Kurita、Akihiro Yokoyama

  DOI：10.1016/j.bioorg.2011.12.002

  日期：2012.4

  We synthesized 12 derivatives of 2,3-bis(bromomethyl) quinoxaline with substituents at the 6-and/or 7-positions, and evaluated their activities against bacteria and fungi. Of the 12 compounds, nine (1a-h, 1j, and 1k) showed antibacterial activity. The derivative 1g, which bears a trifluoromethyl group at the 6-position, showed the highest activity against Gram-positive bacteria, while 1c, which has a fluoro-group at the 6-position, showed the widest antifungal activity spectrum. However, only the derivative with an ethyl ester substitution, 1k showed activity against Gram-negative bacteria. (C) 2012 Elsevier Inc. All rights reserved.
• Luminescent bis(benzo[<i>d</i>]thiazolyl)quinoxaline: facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application
  作者：Lavanya Thilak Babu、Gajanan Raosaheb Jadhav、Priyankar Paira

  DOI：10.1039/c9ra01498e

  日期：——

  A series of luminescent bis(benzo[d]thiazolyl)quinoxalines have been synthesized and their fluorescence properties, anticancer potency, DNA and BSA interactions, cellular uptake, and metabolic stabilities are investigated.

  已合成一系列发光的双(苯并[d]噻唑基)喹喔啉化合物，并研究了它们的荧光特性、抗癌效力、与DNA和BSA的相互作用、细胞摄取以及代谢稳定性。
• Synthesis of 2,3-Bis(halomethyl)quinoxaline Derivatives and Evaluation of Their Antibacterial and Antifungal Activities
  作者：Hisato Ishikawa、Takayuki Sugiyama、Akihiro Yokoyama

  DOI：10.1248/cpb.c12-01061

  日期：——

  Quinoxaline derivatives having bis(fluoromethyl), bis(chloromethyl), or bis(iodomethyl) groups at the 2- and 3-positions, and various electron-donating/withdrawing substituents at the 6- and/or 7-positions, were synthesized. Their antibacterial and antifungal activities were evaluated by means of minimum inhibitory concentration assays. The relationships between the substituents and the antimicrobial activities of the quinoxaline derivatives indicate that the electrophilicity of the halomethyl units plays an important role in generating the antimicrobial activity.

  合成了在2位和3位具有双（氟甲基）、双（氯甲基）或双（碘甲基）基团，在6位和/或7位具有各种电子给体/电子受体取代基的喹喔啉衍生物。通过最小抑菌浓度测定法评估了它们的抗菌和抗真菌活性。喹喔啉衍生物的取代基与抗菌活性之间的关系表明，卤甲基单元的电负性在产生抗菌活性方面起着重要作用。