N-(3,5-dimethoxy-2-methoxyacetylphenyl)-3,4-dimethoxybenzamide | 1026457-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,5-dimethoxy-2-methoxyacetylphenyl)-3,4-dimethoxybenzamide
• 英文别名: N-(3,5-dimethoxy-2-(2-methoxyacetyl)phenyl)-3,4-dimethoxybenzamide；N-[3,5-dimethoxy-2-(2-methoxyacetyl)phenyl]-3,4-dimethoxybenzamide
• CAS: 1026457-04-4
• 化学式: C₂₀H₂₃NO₇
• 分子量: 389.405
• InChiKey: CSTNAMLGZWNCCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(3,5-dimethoxy-2-methoxyacetylphenyl)-3,4-dimethoxybenzamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 160.0~165.0 ℃ 、1.24 MPa 条件下， 反应 3.0h， 以36%的产率得到3,5,7-trimethoxy-2-(3,4-dimethoxyphenyl)-4-oxo-1,4-dihydroquinoline
  参考文献：
  名称：

  Synthesis and topoisomerase inhibitory activities of novel aza-analogues of flavones11Part of the work was presented at the XIVth International Symposium on Medicinal Chemistry, Maastricht, NL, 1996 (Abst. P–10.17)

  摘要：

  A series of aza-flavones (3-hydroxy-2-phenyl-4-quinolones) were designed and synthesized as inhibitors of bacterial DNA-gyrase and mammalian topoisomerase II. Structure activity relationships of the compounds against each of the enzymes are discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80087-7
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 吡啶 、 三氯化硼 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 41.75h， 生成 N-(3,5-dimethoxy-2-methoxyacetylphenyl)-3,4-dimethoxybenzamide
  参考文献：
  名称：

  Synthesis and topoisomerase inhibitory activities of novel aza-analogues of flavones11Part of the work was presented at the XIVth International Symposium on Medicinal Chemistry, Maastricht, NL, 1996 (Abst. P–10.17)

  摘要：

  A series of aza-flavones (3-hydroxy-2-phenyl-4-quinolones) were designed and synthesized as inhibitors of bacterial DNA-gyrase and mammalian topoisomerase II. Structure activity relationships of the compounds against each of the enzymes are discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80087-7

文献信息

• Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors
  作者：Václav Zima、Kateřina Radilová、Milan Kožíšek、Carlos Berenguer Albiñana、Elena Karlukova、Jiří Brynda、Jindřich Fanfrlík、Miroslav Flieger、Jan Hodek、Jan Weber、Pavel Majer、Jan Konvalinka、Aleš Machara

  DOI：10.1016/j.ejmech.2020.112754

  日期：2020.12

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.
• Synthesis and topoisomerase inhibitory activities of novel aza-analogues of flavones11Part of the work was presented at the XIVth International Symposium on Medicinal Chemistry, Maastricht, NL, 1996 (Abst. P–10.17)
  作者：Zhihua Sui、Van N Nguyen、Jason Altom、Jeffrey Fernandez、Jamese J Hilliard、Jeffrey I Bernstein、John F Barrett、Kwasi A Ohemeng

  DOI：10.1016/s0223-5234(99)80087-7

  日期：1999.5

  A series of aza-flavones (3-hydroxy-2-phenyl-4-quinolones) were designed and synthesized as inhibitors of bacterial DNA-gyrase and mammalian topoisomerase II. Structure activity relationships of the compounds against each of the enzymes are discussed. (C) Elsevier, Paris.