1-(furan-2-yl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione | 92189-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(furan-2-yl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione
• 英文别名: 1-Furyl-(2)-<2-hydroxy-5-methoxy-phenyl>-propan-1,3-dion；1-Furyl-(2)-(2-hydroxy-5-methoxy-phenyl)-propan-1,3-dion
• CAS: 92189-09-8
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: WULDXKAKCGMFDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 2-furan-2-yl-6-methoxy-chromen-4-one
  参考文献：
  名称：

  Assessment of antiplatelet activity of 2-aminopyrimidines

  摘要：

  A series of 4,6-diaryl-2-aminopyrimidines was developed as antiplatelet agents and their potency was evaluated by in vitro assay. Compound 14k was found to be two times more potent than aspirin. These encouraging results could be helpful for the development of new antiplatelet compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.035
• 作为产物：
  描述：

  2-acetyl-4-methoxyphenyl furan-2-carboxylate 在 potassium carbonate 作用下， 以 吡啶 为溶剂， 以70%的产率得到1-(furan-2-yl)-3-(2-hydroxy-5-methoxyphenyl)propane-1,3-dione
  参考文献：
  名称：

  多功能Chromeno[2,3-c]pyrrol-9(2H)-ones的合成：4-(二甲氨基)吡啶催化Baker-Venkataraman重排反应的研究与应用

  摘要：

  描述了从 1,3-二芳基-1,3-二酮和氨基酸中高效一锅合成多功能 chromeno[2,3-c]pyrrol-9(2H)-ones。该合成基于 4-（二甲氨基）吡啶催化的 Baker-Venkataraman 重排和后续反应。

  DOI：

  10.1002/ejoc.201100435

文献信息

• Synthesis of Multi-Functionalized Chromeno[2,3-c]pyrrol-9(2H)-ones: Investigation and Application of Baker-Venkataraman Rearrangement Involved Reactions Catalyzed by 4-(Dimethylamino)pyridine
  作者：Yanjun Yu、Yun Hu、Weiyan Shao、Jianing Huang、Yinglin Zuo、Yingpeng Huo、Linkun An、Jun Du、Xianzhang Bu

  DOI：10.1002/ejoc.201100435

  日期：2011.8

  An efficient one-pot synthesis of multi-functionalized chromeno[2,3-c]pyrrol-9(2H)-ones from 1,3-diaryl-1,3-diketones and amino acids is described. The synthesis is based on the 4-(dimethylamino)pyridine-catalyzed Baker–Venkataraman rearrangement and subsequent reactions.

  描述了从 1,3-二芳基-1,3-二酮和氨基酸中高效一锅合成多功能 chromeno[2,3-c]pyrrol-9(2H)-ones。该合成基于 4-（二甲氨基）吡啶催化的 Baker-Venkataraman 重排和后续反应。
• Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure
  作者：Na-Na Shang、Yong-Xian Shao、Ying-Hong Cai、Matthew Guan、Manna Huang、Wenjun Cui、Lin He、Yan-Jun Yu、Lei Huang、Zhe Li、Xian-Zhang Bu、Hengming Ke、Hai-Bin Luo

  DOI：10.1016/j.bcp.2014.02.013

  日期：2014.5

  Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 angstrom resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors. (C) 2014 Elsevier Inc. All rights reserved.
• Assessment of antiplatelet activity of 2-aminopyrimidines
  作者：Rajani Giridhar、Riyaj S. Tamboli、R. Ramajayam、Dhaval G. Prajapati、M.R. Yadav

  DOI：10.1016/j.ejmech.2012.01.035

  日期：2012.4

  A series of 4,6-diaryl-2-aminopyrimidines was developed as antiplatelet agents and their potency was evaluated by in vitro assay. Compound 14k was found to be two times more potent than aspirin. These encouraging results could be helpful for the development of new antiplatelet compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.