3-(4-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one | 115883-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one
• 英文别名: 4-hydroxy-3-(2-methoxyphenyl)furan-2(5H)-one；2-(4-benzyloxyphenyl)-3-hydroxy-2-buten-4-olide；3-hydroxy-4-(4-phenylmethoxyphenyl)-2H-furan-5-one
• CAS: 115883-14-2
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: LPCDETHBBFQOLP-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  516.5±50.0 °C(predicted)
• 密度：
  1.335±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 4-(3,5-dichlorophenylamino)-3-(4-hydroxyphenyl)furan-2(5H)-one
  参考文献：
  名称：

  Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones

  摘要：

  Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5-dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC50 of 0.09 +/- 0.02 mu M. The structure activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC50 of 0.06 mu g/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.047
• 作为产物：
  描述：

  4-苄氧基苯乙酸 在 sodium ethanolate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.17h， 生成 3-(4-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one
  参考文献：
  名称：

  4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

  摘要：

  A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 27 is the most potent agent against Staphylococcus ;aureus ATCC 25923 with MIC50 value of 0.23 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.042

文献信息

• Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
  作者：Xiaotan Yu、Xiaoxia Gu、Yunpeng Zhao、Fengqing Wang、Weiguang Sun、Changxing Qi、Lianghu Gu、Yonghui Zhang

  DOI：10.1039/d2ra08133d

  日期：——

  mild, modular and efficient synthetic method with broad substrate scope was developed for aspulvinones. Nine natural aspulvinones were synthesized, six of which were for the first time. The aldol condensation delivered Z-configuration products predominantly in MeCN. Meanwhile, alkoxy exchange occurred in MeOH and EtOH. Aspulvinone O and E, and substrate 49, 50, and 51 exhibited modest anti-SARS-CoV-2

  开发了一种温和、模块化、高效且底物适用范围广的阿斯普维酮合成方法。合成了九种天然阿斯普维酮，其中六种为首次合成。羟醛缩合主要在 MeCN 中提供 Z 构型产品。同时，MeOH和EtOH发生烷氧基交换。Aspulvinone O 和 E，以及底物 49、50 和 51 在高通量筛选和酶动力学测定中表现出适度的抗 SARS-CoV-2 活性。
• 4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation
  作者：Zhu-Ping Xiao、Hui Ouyang、Xu-Dong Wang、Peng-Cheng Lv、Ze-Jun Huang、She-Rong Yu、Tian-Fang Yi、Ye-Ling Yang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.05.042

  日期：2011.7

  A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 27 is the most potent agent against Staphylococcus ;aureus ATCC 25923 with MIC50 value of 0.23 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.
• Hydroxybutenolide derivatives, production and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0259707B1

  公开（公告）日：1992-01-02
• US4939274A
  申请人：——

  公开号：US4939274A

  公开（公告）日：1990-07-03
• Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones
  作者：Zhu-Ping Xiao、Tao-Wu Ma、Mei-Lin Liao、Yu-Ting Feng、Xiao-Chun Peng、Jia-Liang Li、Zhi-Ping Li、Ying Wu、Qun Luo、Yang Deng、Xiao Liang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.07.047

  日期：2011.10

  Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5-dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC50 of 0.09 +/- 0.02 mu M. The structure activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC50 of 0.06 mu g/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity. (C) 2011 Elsevier Masson SAS. All rights reserved.