methyl 2-(2-(benzyloxy)-5-formylphenoxy)acetate | 1346225-91-9

• 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: methyl 2-(2-(benzyloxy)-5-formylphenoxy)acetate
• 英文别名: Methyl 2-(5-formyl-2-phenylmethoxyphenoxy)acetate
• CAS: 1346225-91-9
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: XRLSQQRIICAYFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-(benzyloxy)-5-formylphenoxy)acetate 在 甲醇 、 potassium carbonate 、 potassium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.0h， 生成 (R)-dimethyl 2-(4-((4-formyl-2-(2-methoxy-2-oxoethoxy)phenoxy)methyl)benzamido)pentanedioate
  参考文献：
  名称：

  New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: Design, synthesis, crystal structures, and biological evaluation

  摘要：

  Mur ligases (MurC-MurF), a group of bacterial enzymes that catalyze four consecutive steps in the formation of cytoplasmic peptidoglycan precursor, are becoming increasingly adopted as targets in antibacterial drug design. Based on the crystal structure of MurD cocrystallized with thiazolidine-2,4-dione inhibitor I, we have designed, synthesized, and evaluated a series of improved glutamic acid containing 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2,4-dione inhibitors of MurD with IC50 values up to 28 mu M. Inhibitor 37, with an IC50 of 34 mu M, displays a weak antibacterial activity against S. aureus ATCC 29213 and E. faecalis ATCC 29212 with minimal inhibitory concentrations of 128 mu g/mL. High-resolution crystal structures of MurD in complex with two new inhibitors (compounds 23 and 51) reveal details of their binding modes within the active site and provide valuable information for further structure-based optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.017
• 作为产物：
  描述：

  氯化苄 在 碳酸氢钠 、 potassium carbonate 、 potassium iodide 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 methyl 2-(2-(benzyloxy)-5-formylphenoxy)acetate
  参考文献：
  名称：

  New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: Design, synthesis, crystal structures, and biological evaluation

  摘要：

  Mur ligases (MurC-MurF), a group of bacterial enzymes that catalyze four consecutive steps in the formation of cytoplasmic peptidoglycan precursor, are becoming increasingly adopted as targets in antibacterial drug design. Based on the crystal structure of MurD cocrystallized with thiazolidine-2,4-dione inhibitor I, we have designed, synthesized, and evaluated a series of improved glutamic acid containing 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2,4-dione inhibitors of MurD with IC50 values up to 28 mu M. Inhibitor 37, with an IC50 of 34 mu M, displays a weak antibacterial activity against S. aureus ATCC 29213 and E. faecalis ATCC 29212 with minimal inhibitory concentrations of 128 mu g/mL. High-resolution crystal structures of MurD in complex with two new inhibitors (compounds 23 and 51) reveal details of their binding modes within the active site and provide valuable information for further structure-based optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.017

文献信息

• 2,2- dimethylbenzopyran derivatives containing pyridone structural fragments as selective dual-targeting inhibitors of HIF-1α and EZH2 for the treatment of lung cancer
  作者：Huashen Xu、Jie Zhang、Junning Zhuang、Yuanguang Chen、Lu Chen、Jianmin Wang、Ruolin Cao、Fuqin Liu、Kaibo Wang、Xiaoyu Zhang、Lihui Wang、Guoliang Chen

  DOI：10.1016/j.bioorg.2024.107419

  日期：2024.4

  levels, and conversely, inhibition of EZH2 promoted HIF-1α transcription. HIF-1α and EZH2 interacted to form a negative feedback loop that reinforced each other's activity. In this paper, a series of 2,2- dimethylbenzopyran derivatives containing pyridone structural fragments were designed and synthesized with , a HIF-1α inhibitor previously reported by our group, and , an EZH2 inhibitor approved by

  我们之前报道，EZH2抑制剂使HIF-1抑制剂耐药细胞敏感，并抑制HIF-1α促进SUZ12转录，导致EZH2酶活性增强和H3K27me3水平升高，反之，抑制EZH2促进HIF-1α转录。 HIF-1α 和 EZH2 相互作用形成负反馈回路，增强彼此的活性。本文以本课题组先前报道的HIF-1α抑制剂和FDA批准的EZH2抑制剂为先导化合物，设计合成了一系列含有吡啶酮结构片段的2,2-二甲基苯并吡喃衍生物。其中，对HIF-1α和EZH2具有显着的抑制活性。体外实验表明，显着抑制A549细胞的迁移、克隆、侵袭和血管生成。此外，具有良好的药代动力学特征。所有有关化合物的研究结果可为HIF-1α和EZH2双靶向化合物的研发奠定基础。
• New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: Design, synthesis, crystal structures, and biological evaluation
  作者：Nace Zidar、Tihomir Tomašić、Roman Šink、Andreja Kovač、Delphine Patin、Didier Blanot、Carlos Contreras-Martel、Andréa Dessen、Manica Müller Premru、Anamarija Zega、Stanislav Gobec、Lucija Peterlin Mašič、Danijel Kikelj

  DOI：10.1016/j.ejmech.2011.09.017

  日期：2011.11

  Mur ligases (MurC-MurF), a group of bacterial enzymes that catalyze four consecutive steps in the formation of cytoplasmic peptidoglycan precursor, are becoming increasingly adopted as targets in antibacterial drug design. Based on the crystal structure of MurD cocrystallized with thiazolidine-2,4-dione inhibitor I, we have designed, synthesized, and evaluated a series of improved glutamic acid containing 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2,4-dione inhibitors of MurD with IC50 values up to 28 mu M. Inhibitor 37, with an IC50 of 34 mu M, displays a weak antibacterial activity against S. aureus ATCC 29213 and E. faecalis ATCC 29212 with minimal inhibitory concentrations of 128 mu g/mL. High-resolution crystal structures of MurD in complex with two new inhibitors (compounds 23 and 51) reveal details of their binding modes within the active site and provide valuable information for further structure-based optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.