3,4-dihydro-2H-8-methoxy-1,4-benzoxazin-6-carbaldehyde | 1367348-64-8

• 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: 3,4-dihydro-2H-8-methoxy-1,4-benzoxazin-6-carbaldehyde
• 英文别名: 8-methoxy-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde
• CAS: 1367348-64-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: YNPDUEYSZMMWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2H-8-methoxy-1,4-benzoxazin-6-carbaldehyde 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以43 %的产率得到(Z)-3,4-dihydro-2H-8-methoxy-1,4-benzoxazin-6-carbaldehyde oxime
  参考文献：
  名称：

  在硅片中寻找不同的磷酸二酯酶 4 抑制剂化学类型以指导抗炎/抗氧化剂的设计

  摘要：

  基于先前磷酸二酯酶 4 (PDE4) 抑制剂的 X 射线数据，化合物1-3被设计、合成并在计算机中筛选为推定的 PDE4 抑制剂，以利用儿茶酚基团的结构变异以获得进一步的接触，尤其是与平面PDE4 的芳香族残基。随后对血小板和内皮细胞进行的体外生物测定为抗氧化和抗炎活性提供了证据。

  DOI：

  10.1002/cmdc.202300046
• 作为产物：
  描述：

  4-(1,3-Dioxolan-2-yl)-2-methoxy-6-nitrophenol 在 三乙基硅烷 、 palladium on activated charcoal 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,4-dihydro-2H-8-methoxy-1,4-benzoxazin-6-carbaldehyde
  参考文献：
  名称：

  Structure aided design of chimeric antibiotics

  摘要：

  The rise of antibiotic resistance is of great clinical concern. One approach to reducing the development of resistance is to co-administer two or more antibiotics with different modes of action. However, it can be difficult to control the distribution and pharmacokinetics of two drugs to ensure both concentrations remain within the range of therapeutic efficacy whilst avoiding adverse effects. Hybrid drugs, where two drugs are linked together with a flexible linker, have been explored, but the resultant large, flexible molecules can have poor bioavailability. We have developed a chimeric approach using click chemistry where the pharmacophores of two drugs are overlapped into a single smaller, more drug-like molecule. Design and selection of compounds were assisted by in silico structural docking. We prepared a series of compounds that include candidates showing activity against the targets of both trimethoprim; dihydrofolate reductase, and ciprofloxacin; DNA gyrase and topoisomerase IV. The resultant triazole containing molecules show modest, but broad spectrum activities against drug sensitive and resistant Gram-negative and Gram-positive bacteria, with no observable cytotoxicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.019

文献信息

• Structure aided design of chimeric antibiotics
  作者：Tomislav Karoli、Sreeman K. Mamidyala、Johannes Zuegg、Scott R. Fry、Ernest H.L. Tee、Tanya A. Bradford、Praveen K. Madala、Johnny X. Huang、Soumya Ramu、Mark S. Butler、Matthew A. Cooper

  DOI：10.1016/j.bmcl.2012.02.019

  日期：2012.4

  The rise of antibiotic resistance is of great clinical concern. One approach to reducing the development of resistance is to co-administer two or more antibiotics with different modes of action. However, it can be difficult to control the distribution and pharmacokinetics of two drugs to ensure both concentrations remain within the range of therapeutic efficacy whilst avoiding adverse effects. Hybrid drugs, where two drugs are linked together with a flexible linker, have been explored, but the resultant large, flexible molecules can have poor bioavailability. We have developed a chimeric approach using click chemistry where the pharmacophores of two drugs are overlapped into a single smaller, more drug-like molecule. Design and selection of compounds were assisted by in silico structural docking. We prepared a series of compounds that include candidates showing activity against the targets of both trimethoprim; dihydrofolate reductase, and ciprofloxacin; DNA gyrase and topoisomerase IV. The resultant triazole containing molecules show modest, but broad spectrum activities against drug sensitive and resistant Gram-negative and Gram-positive bacteria, with no observable cytotoxicity. (C) 2012 Elsevier Ltd. All rights reserved.
• Scouting Different Phosphodiesterase 4 Inhibitor Chemotypes in Silico To Guide the Design of Anti‐inflammatory/Antioxidant Agents
  作者：Elena Cichero、Federica Rapetti、Matteo Lusardi、Naomi Scarano、Silvana Alfei、Paola Altieri、Silvano Garibaldi、Pietro Ameri、Maria Grazia Signorello、Chiara Brullo

  DOI：10.1002/cmdc.202300046

  日期：——

  Based on the X-ray data of previous phosphodiesterase 4 (PDE4) inhibitors, compounds 1–3 were designed, synthesized, and screened in silico as putative PDE4 inhibitors to exploit structural variation at the catechol group to gain further contacts, especially with the flat aromatic residues of PDE4. Subsequent in vitro biological assays on platelets and endothelial cells provided evidence for antioxidant

  基于先前磷酸二酯酶 4 (PDE4) 抑制剂的 X 射线数据，化合物1-3被设计、合成并在计算机中筛选为推定的 PDE4 抑制剂，以利用儿茶酚基团的结构变异以获得进一步的接触，尤其是与平面PDE4 的芳香族残基。随后对血小板和内皮细胞进行的体外生物测定为抗氧化和抗炎活性提供了证据。