6-(morpholine-4-sulfonyl)-1,4-dihydroquinoxaline-2,3-dione

• 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: 6-(morpholine-4-sulfonyl)-1,4-dihydroquinoxaline-2,3-dione
• 英文别名: 6-Morpholin-4-ylsulfonyl-1,4-dihydroquinoxaline-2,3-dione
• 化学式: C₁₂H₁₃N₃O₅S
• 分子量: 311.318
• InChiKey: CHWYWIAZSUIAFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(morpholine-4-sulfonyl)-1,4-dihydroquinoxaline-2,3-dione 在 五氯化磷 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 2,3-disulfanilamildoquinoxaline-6-morpholyl sulfonamide
  参考文献：
  名称：

  El-Sharief; Ali; Ammar, Pakistan Journal of Scientific and Industrial Research, 1996, vol. 39, # 1-4, p. 5 - 10

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二羟基喹喔啉 在 氯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 6-(morpholine-4-sulfonyl)-1,4-dihydroquinoxaline-2,3-dione
  参考文献：
  名称：

  Synthesis of some sulfonamide derivatives with potential antibacterial activity

  摘要：

  DOI：

  10.1007/bf02269544

文献信息

• Experimental and theoretical investigation for 6-Morpholinosulfonylquinoxalin-2(1H)-one and its haydrazone derivate: Synthesis, characterization, tautomerization and antimicrobial evaluation
  作者：Doaa M. Elsisi、Ahmed Ragab、Ahmed A. Elhenawy、Awatef A. Farag、Abeer M. Ali、Yousry A. Ammar

  DOI：10.1016/j.molstruc.2021.131314

  日期：2022.1

  synthesize a safe antimicrobial agent based on dihydroquinoxalinedione derivatives. The structure of the synthesized compounds was established based on different spectral data. The antimicrobial activity for the tested compounds was evaluated against eight pathogens. Also, the ADMET was measured to identify toxicity prediction, lipophilicity, bioactivity, and pharmacophores for antimicrobial activities for

  这项工作旨在合成一种基于二氢喹喔啉二酮衍生物的安全抗菌剂。根据不同的光谱数据确定合成化合物的结构。针对八种病原体评估了测试化合物的抗微生物活性。此外，还测量了 ADMET，以确定这些化合物的毒性预测、亲脂性、生物活性和药效团的抗菌活性。互变异构过程的存在是控制抗菌活性方向的主要因素。因此，已执行 DFT 以鉴定 B3LYP/6-311G* 水平的物理化学参数，以获得对全局和局部分子反应性的清晰视图。此外，合成化合物的分子特征通过 HOMO、绘制 LUMO 和 MEP（分子静电势）以确定分子内的电荷转移。此外，DFT 计算已用于获得全局和局部分子反应性的清晰视图。讨论了合成化合物的 NLO 特性，其显示出比参考度量更高的特性。通过 DHPS 进行分子对接以使观察到的抗菌活性合理化。化合物2和5代表显着的交互得分。通过分子动力学模拟检查对接配体的稳定性，这表明测试化合物进入活性位点具有高稳定性
• Design, synthesis, antimicrobial activity and molecular docking studies of some novel di-substituted sulfonylquinoxaline derivatives
  作者：Yousry A. Ammar、Awatef A. Farag、Abeer M. Ali、Ahmed Ragab、Ahmed A. Askar、Doaa M. Elsisi、Amany Belal

  DOI：10.1016/j.bioorg.2020.104164

  日期：2020.11

  quinoxaline derivatives 11a-c. Additionally triazolo and pyrazolyl quinoxaline derivatives 12–14 were obtained through the reaction of compound 11a with phenyl isothiocyanate, formylpyrazole and ethyl acetoacetate. All the synthesized compounds were screened for their antibacterial and antifungal activities. Compounds 7a, 9b, 10a, 10c, 10f and 11c showed good to moderate antimicrobial activity against

  通过邻苯二胺与草酸反应，然后用过量的氯磺酸进行氯磺化反应，制得2，3-二氧-1,2,3,4-四氢喹喔啉-6-磺酰氯1。一系列新sulfonylquinoxaline衍生物的2 - 6在化合物反应，得到1与不同类型的胺。2,3-二氯-6- morpholinosulfonylquinoxaline衍生物6进行进一步的化学反应，得到6-吗啉代的许多衍生物2,3- disubstitutedquinoxalines，从而化合物的反应6具有不同的仲胺，得到单和二仲氨基喹喔啉衍生物7 - 10取决于两个氯原子的反应性差异。化合物7提供的肼基喹喔啉衍生物11a-c的水合肼解。此外三唑和吡唑基喹喔啉衍生物12 - 14是通过化合物的反应获得11A与异硫氰酸苯酯，甲酰基和乙酰乙酸乙酯。筛选所有合成的化合物的抗菌和抗真菌活性。化合物7a，9b，10a，10c，10f和11c对被测革兰氏阳性，革兰氏阴性细菌和
• Antimicrobial evaluation of thiadiazino and thiazolo quinoxaline hybrids as potential DNA gyrase inhibitors; design, synthesis, characterization and morphological studies
  作者：Yousry A. Ammar、Awatef A. Farag、Abeer M. Ali、Sadia A. Hessein、Ahmed A. Askar、Eman A. Fayed、Doaa M. Elsisi、Ahmed Ragab

  DOI：10.1016/j.bioorg.2020.103841

  日期：2020.6

  A series of thiadiazino[5,6-b]quinoxaline and thiazolo[4,5-b]quinoxaline derivatives was designed and synthetized from the reaction of 2,3-dichloro-6-(morpholinosulfonyl)quinoxaline (2) with thiosemicarbazide or thiocarbohydrazide and thiourea derivatives to give nineteen quinoxaline derivatives 3-16. All the synthesized compounds were evaluated for in vitro antimicrobial potential against various bacteria and fungi strains that showed considerable antimicrobial activity against tested microorganisms. The most potent compounds 2, 7, 9, 10, 12 and 13c were exhibited bactericidal activity, in addition to fungistatic activity by dead live assay. Moreover, these compounds showed a significant result against all multi-drug resistance (MDRB) used especially compound 13c that displayed the best results with MICs of MDRB (1.95, 3.9, 2.6, 3.9 mu g/mL) for stains used in this study, compared with Norfloxacin (1.25, 0.78, 1.57, 3.13 mu g/mL). Also, cytotoxicity on normal cell (Vero cells ATCC CCL-81) by MTT assay was performed with lower toxicity results. Additionally, morphological studies, immunostimulatory potency and DNA gyrase inhibition assay of most active compounds was done. A molecular docking study has also been carried out to support the effective binding of the most promising compounds at the active site of the target enzyme S. aureus DNA gyrase (2XCT).
• US5912245A
  申请人：——

  公开号：US5912245A

  公开（公告）日：1999-06-15