2-羟基-6,7-二甲氧基-3-甲基喹喔啉 | 5762-66-3

• 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-羟基-6,7-二甲氧基-3-甲基喹喔啉
• 中文别名: 4,5-二(4-甲氧苯基)-1H-吡唑-3-胺
• 英文名称: 6,7-dimethoxy-3-methylquinoxalin-2(1H)-one
• 英文别名: 2-Hydroxy-6,7-dimethoxy-3-methylquinoxaline；6,7-dimethoxy-3-methyl-1H-quinoxalin-2-one
• CAS: 5762-66-3
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: AIWLGDWWEZIPIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 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：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-6,7-二甲氧基-3-甲基喹喔啉 在 N-甲基吗啉 、 硫酸 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 、 potassium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 17.5h， 生成 (Z)-2-(6,7-dimethoxy-2-oxo-3-(2-(pyridin-4-yl)vinyl)quinoxalin-1(2H)-yl)-N-phenylacetamide
  参考文献：
  名称：

  Quinoxalinone (Part II). Discovery of (Z)-3-(2-(pyridin-4-yl)vinyl)quinoxalinone derivates as potent VEGFR-2 kinase inhibitors

  摘要：

  Inhibition of VEGFR-2 kinase has been highlighted as one of the well-defined strategies to suppress tumor growth via blockade of angiogenesis. Guided by the principles of bioisosteric replacement and pharmacophoric fragment migration, a series of novel quinoxalinone derivates were designed, synthesized and evaluated for their VEGFR-2 inhibitory potencies. Among them, compounds 7c, 8b, 8c, 8e and 10b displayed antiangiogenic abilities via the in vitro tube formation assay (cellular level) and ex vivo rat aortic ring assay (tissue level) at a low concentration (0.1 mu M). By means of in vivo zebrafish embryo model, two (Z)-3-(2-(pyridin-4-yl)vinyl)quinoxalinone derivates 8c and 8e showed significant antiangiogenesis effects, suggesting they have potentials to be developed into antiangiogenesis agents via further structural optimization. Moreover, these two compounds also demonstrated potent inhibition toward VEGFR-2 and B-raf kinases in a low concentration (1 mu M). A possible interpretation of our evaluation result has been presented by a molecular docking study by docking representative compound 8c with VEGFR-2. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.008
• 作为产物：
  描述：

  1,2-二甲氧基-4-二硝基苯 在 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-羟基-6,7-二甲氧基-3-甲基喹喔啉
  参考文献：
  名称：

  Fluorogenic Enzyme-Triggered Domino Reactions Producing Quinoxalin-2(1H)-one-based Heterocycles

  摘要：

  A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and the ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly"-based fluorescent probe in the fields of sensing and bioimaging.

  DOI：

  10.1021/acs.orglett.0c02287

文献信息

• Nucleotide sequences of coryneform bacteria coding for proteins involved in l-serine metabolism and method for producing l-serine
  申请人：Peters-Wendisch Petra

  公开号：US20060204963A1

  公开（公告）日：2006-09-14

  The invention relates to the nucleotide sequences of coryneform bacteria coding for proteins which are involved in L-serine metabolism with reduced and switched off L-serine dehydratase. Said invention also relates to micro-organisms and to methods for producing L-serine.

  本发明涉及编码参与 L-丝氨酸代谢的 L-丝氨酸脱水酶减少和关闭的蛋白质的伞菌核苷酸序列。本发明还涉及微生物和生产 L-丝氨酸的方法。
• Hara, Shuuji; Yamaguchi, Masatoshi; Nakamura, Masaru, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 8, p. 3493 - 3498
  作者：Hara, Shuuji、Yamaguchi, Masatoshi、Nakamura, Masaru、Ohkura, Yosuke

  DOI：——

  日期：——
• NUCLEOTIDE SEQUENCES OF CORYNEFORM BACTERIA CODED FOR PROTEINS PARTICIPATING IN L-SERINE METABOLISM AND METHOD FOR MICROBIAL PRODUCTION OF L-SERINE
  申请人：Peters-Wendisch Petra

  公开号：US20090061482A1

  公开（公告）日：2009-03-05

  This invention relates to the nucleotide sequence of coryneform bacteria coding for proteins which are involved in L-serine metabolism with reduced and switched off L-serine dehydratase activity. The invention also relates to microorganisms used in methods for producing L-serine.
• US8119374B2
  申请人：——

  公开号：US8119374B2

  公开（公告）日：2012-02-21
• Fluorogenic Enzyme-Triggered Domino Reactions Producing Quinoxalin-2(1<i>H</i>)-one-based Heterocycles
  作者：Garance Dejouy、Kévin Renault、Quentin Bonnin、Arnaud Chevalier、Cédric Michaudet、Michel Picquet、Ibai E. Valverde、Anthony Romieu

  DOI：10.1021/acs.orglett.0c02287

  日期：2020.8.21

  A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and the ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly"-based fluorescent probe in the fields of sensing and bioimaging.