2,3-二甲氧基-6-甲基-喹喔啉 | 69722-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2,3-二甲氧基-6-甲基-喹喔啉
• 英文名称: 2,3-dimethoxy-6-methyl-quinoxaline
• 英文别名: 2,3-Dimethoxy-6-methyl-chinoxalin；2,3-Dimethoxy-6-methylquinoxaline
• CAS: 69722-50-5
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: VLACLKWCHQHLHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲氧基-6-甲基-喹喔啉 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以76%的产率得到6-溴甲基-2,3-二甲氧基-喹噁啉
  参考文献：
  名称：

  Quinoxaline chemistry Part 9. Quinoxaline analogues of trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) and its precursors. Synthesis and evaluation of in vitro anticancer activity

  摘要：

  Eighteen quinoxalines bearing a methyleneanilino or methyleneaminobenzoylglutamate group on position 6 of the ring and various lipophilic substituents on positions 2 and 3 were prepared in order to discover if their structural analogy with both trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) might display in vitro anticancer activity. Among these, 12 compounds were selected at the National Cancer Institute, Bethesda, MD, USA; they exhibited moderate (4b,d,i,l,m and 8) to strong (4f,h and 5a,e) cell-growth inhibition at a concentration of 10(-4) M. Interesting selectivities were also recorded between 10(-8) and 10(-6) M. These analogues proved to be less potent inihibitors of tumor cells than other classical and non-classical antifolate analogues previously described by us. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00002-0
• 作为产物：
  描述：

  2,3-二羟基-6-甲基喹喔啉 在 三氯氧磷 作用下， 生成 2,3-二甲氧基-6-甲基-喹喔啉
  参考文献：
  名称：

  275.合成抗疟药。第XL部分。2-氯-3 - β-二乙基氨基乙基氨基喹喔啉中取代基变化的影响

  摘要：

  DOI：

  10.1039/jr9490001271

文献信息

• US4184977A
  申请人：——

  公开号：US4184977A

  公开（公告）日：1980-01-22
• USRE30352E
  申请人：——

  公开号：USRE30352E

  公开（公告）日：1980-07-29
• [EN] INHIBITORS OF ALPHA-HEMOLYSIN OF STAPHYLOCOCCUS AUREUS<br/>[FR] INHIBITEURS DE L'ALPHA-HÉMOLYSINE DE STAPHYLOCOCCUS AUREUS
  申请人：[en]HELMHOLTZ-ZENTRUM FÜR INFEKTIONSFORSCHUNG GMBH

  公开号：WO2023280970A1

  公开（公告）日：2023-01-12

  The present invention relates to novel inhibitors of α-hemolysin of formula (I) and the use thereof for the prophylaxis and treatment of infections caused byStaphylococcusaureus; especiallyS. aureuslung infections.
• 275. Synthetic antimalarials. Part XL. The effect of variation of substituents in 2-chloro-3-β-diethylaminoethylaminoquinoxaline
  作者：F. H. S. Curd、D. G. Davey、G. J. Stacey

  DOI：10.1039/jr9490001271

  日期：——
• Quinoxaline chemistry Part 9. Quinoxaline analogues of trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) and its precursors. Synthesis and evaluation of in vitro anticancer activity
  作者：Mario Loriga、Gabriella Vitale、Giuseppe Paglietti

  DOI：10.1016/s0014-827x(98)00002-0

  日期：1998.2

  Eighteen quinoxalines bearing a methyleneanilino or methyleneaminobenzoylglutamate group on position 6 of the ring and various lipophilic substituents on positions 2 and 3 were prepared in order to discover if their structural analogy with both trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) might display in vitro anticancer activity. Among these, 12 compounds were selected at the National Cancer Institute, Bethesda, MD, USA; they exhibited moderate (4b,d,i,l,m and 8) to strong (4f,h and 5a,e) cell-growth inhibition at a concentration of 10(-4) M. Interesting selectivities were also recorded between 10(-8) and 10(-6) M. These analogues proved to be less potent inihibitors of tumor cells than other classical and non-classical antifolate analogues previously described by us. (C) 1998 Elsevier Science S.A. All rights reserved.