1-(6,7-dichloro-3-methyl-1,4-dioxyquinoxaline-2-yl)ethanone | 380576-08-9

• 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: 1-(6,7-dichloro-3-methyl-1,4-dioxyquinoxaline-2-yl)ethanone
• 英文别名: Ethanone, 1-(6,7-dichloro-3-methyl-1,4-dioxido-2-quinoxalinyl)-；1-(6,7-dichloro-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)ethanone
• CAS: 380576-08-9
• 化学式: C₁₁H₈Cl₂N₂O₃
• 分子量: 287.102
• InChiKey: UYEJSNFETDFBSI-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C(Solv: methanol (67-56-1))
• 沸点：
  515.0±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6,7-dichloro-3-methyl-1,4-dioxyquinoxaline-2-yl)ethanone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 氯仿 为溶剂， 反应 24.0h， 以84%的产率得到Ethanone, 1-[3-(bromomethyl)-6,7-dichloro-1,4-dioxido-2-quinoxalinyl]-
  参考文献：
  名称：

  Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents

  摘要：

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00137-5
• 作为产物：
  描述：

  5,6-dichlorobenzofuroxan 、 乙酰丙酮 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以71%的产率得到1-(6,7-dichloro-3-methyl-1,4-dioxyquinoxaline-2-yl)ethanone
  参考文献：
  名称：

  Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents

  摘要：

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00137-5

文献信息

• Design and synthesis of novel quinoxaline derivatives as potential candidates for treatment of multidrug-resistant and latent tuberculosis
  作者：Mery Santivañez-Veliz、Silvia Pérez-Silanes、Enrique Torres、Elsa Moreno-Viguri

  DOI：10.1016/j.bmcl.2016.03.066

  日期：2016.5

  Twenty-four quinoxaline derivatives were evaluated for their antimycobacterial activity using BacTiter-Glo microbial cell viability assay. Five compounds showed MIC values <3.1 μM and IC50 values <1.5 μM in primary screening and therefore, they were moved on for further evaluation. Compounds 21 and 18 stand out, showing MIC values of 1.6 μM and IC50 values of 0.5 and 1.0 μM, respectively. Both compounds

  使用BacTiter-Glo微生物细胞生存力测定法评估了24种喹喔啉衍生物的抗分枝杆菌活性。五个化合物在初次筛选时的MIC值<3.1μM，IC 50值<1.5μM，因此，他们继续进行进一步的评估。化合物21和18脱颖而出，分别显示MIC值为1.6μM和IC 50值为0.5和1.0μM。两种化合物对三种评估的耐药菌株均最有效。此外，考虑到对数减少和细胞活力，它们在感染的巨噬细胞中表现出细胞内活性。此外，化合物16和21对非复制有效结核分枝杆菌和化合物21具有杀菌作用。因此，可以考虑使用喹喔啉衍生物在抗分枝杆菌药的未来发展中取得进一步的进展。
• Silica Gel Catalyzed Synthesis of Quinoxaline 1,4-Dioxides under Solvent-Free Conditions Using Microwave Irradiation
  作者：Tohru Takabatake、Yusuke Sumiyoshi、Hiroaki Saito、Shinichi Miyairi

  DOI：10.3987/com-08-11588

  日期：——

  We report on the simple and quick synthesis of quinoxaline 1,4-dioxides in solvent-free conditions under microwave irradiation. Heating of various benzofuroxans and beta-ketoesters or 1,3-diketones adsorbed on silica gel in a microwave oven for two minutes affords diverse biologically attractive quinoxaline 1,4-dioxides in high to excellent yields. Silica gel functions not only as support using microwave but also as catalyst and dehydration reagent.
• Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents
  作者：Andrés Jaso、Belén Zarranz、Ignacio Aldana、Antonio Monge

  DOI：10.1016/s0223-5234(03)00137-5

  日期：2003.9

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.