6-(4-methoxyphenyl)-5,7,8-trimethyl-3,4-dihydro-2H-1,4-benzoxazine | 1277193-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-(4-methoxyphenyl)-5,7,8-trimethyl-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 1277193-48-2
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: PUCLHQVMBQCZDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基-3,5,6-三甲基苯酚 在 四(三苯基膦)钯 、 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 氢溴酸 、 氢气 、 双氧水 、 四丁基碘化铵 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 3.08h， 生成 6-(4-methoxyphenyl)-5,7,8-trimethyl-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  Regulation of the Escherichia coli AtoSC two component system by synthetic biologically active 5;7;8-trimethyl-1;4-benzoxazine analogues

  摘要：

  The Escherichia coli AtoSC two component system; upon acetoacetate induction; regulates the expression of the atoDAEB operon; through His -> Asp phopshotransfer; thus modulating important cellular processes. In this report the effect of seven 5,7,8-trimethyl-1,4-benzoxazine derivatives on the regulation of the E. coli AtoSC system was studied. The new compounds were tested for their effectiveness on the expression of the atoC and the regulated atoDAEB operon. The non-substituted 5,7,8-trimethyl-1,4-benzoxazine (4a), was the most potent inducer on atoC transcription; resulting in accumulation of AtoC protein. The induction of atoC by 4a was specific; since no effect was observed on the other genes of the system (atoS and atoDAEB). Moreover; compound 4a was shown to significantly up-regulate the in vitro kinase activity of the histidine kinase AtoS without altering the protein levels in the cell. Interestingly; this compound appeared to modulate the acetoacetate-mediated induction of the atoDAEB promoter by the AtoSC system. These data provide the first evidence for a differential modulator role of 5,7,8-trimethyl-1,4-benzoxazine; on the AtoSC two component system mediated signaling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.029

文献信息

• Regulation of the Escherichia coli AtoSC two component system by synthetic biologically active 5;7;8-trimethyl-1;4-benzoxazine analogues
  作者：Panagiota S. Filippou、Eftychia N. Koini、Theodora Calogeropoulou、Panagiota Kalliakmani、Christos A. Panagiotidis、Dimitrios A. Kyriakidis

  DOI：10.1016/j.bmc.2011.06.029

  日期：2011.8

  The Escherichia coli AtoSC two component system; upon acetoacetate induction; regulates the expression of the atoDAEB operon; through His -> Asp phopshotransfer; thus modulating important cellular processes. In this report the effect of seven 5,7,8-trimethyl-1,4-benzoxazine derivatives on the regulation of the E. coli AtoSC system was studied. The new compounds were tested for their effectiveness on the expression of the atoC and the regulated atoDAEB operon. The non-substituted 5,7,8-trimethyl-1,4-benzoxazine (4a), was the most potent inducer on atoC transcription; resulting in accumulation of AtoC protein. The induction of atoC by 4a was specific; since no effect was observed on the other genes of the system (atoS and atoDAEB). Moreover; compound 4a was shown to significantly up-regulate the in vitro kinase activity of the histidine kinase AtoS without altering the protein levels in the cell. Interestingly; this compound appeared to modulate the acetoacetate-mediated induction of the atoDAEB promoter by the AtoSC system. These data provide the first evidence for a differential modulator role of 5,7,8-trimethyl-1,4-benzoxazine; on the AtoSC two component system mediated signaling. (C) 2011 Elsevier Ltd. All rights reserved.