N,N-diethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: N,N-diethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester
• 英文别名: 4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyldiethylcarbamate；N,N-diethylcarbamic acid-4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester (7b)；[4-(5,6,7-trihydroxy-4-oxochromen-2-yl)phenyl] N,N-diethylcarbamate
• 化学式: C₂₀H₁₉NO₇
• 分子量: 385.373
• InChiKey: QGTBKSTUWGAYSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-diethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester 、 tert-butyl (2S)-2-isocyanato-3-phenylpropanoate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of novel scutellarin and scutellarein-N,N-bis-substituted carbamate-l-amino acid derivatives as potential multifunctional therapeutics for Alzheimer’s disease

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105760
• 作为产物：
  描述：

  野黄芩素 在 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 邻二氯苯 、 乙腈 为溶剂， 生成 N,N-diethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Scutellarein Carbamate Derivatives as Potential Multifunctional Agents for the Treatment of Alzheimer's Disease

  摘要：

  A series of scutellarein carbamate derivatives were designed and synthesized based on the multitarget‐directed drug design strategy for treatment of Alzheimer's disease. Their acetylcholinesterase and butyrylcholinesterase inhibitory activities, antioxidant activities, metals chelation, and neuroprotective effects against hydrogen peroxide‐induced PC12 cell injury were evaluated in vitro. The preliminary results indicated that compound 7b exhibited good inhibitory potency toward AChE and BuChE with IC50 values of 1.2 ± 0.03 μm and 22.1 ± 0.15 μm, respectively, possessed the strong antioxidant potency (10.3 trolox equivalents), as well as acted as a selective metal chelator and neuroprotective agent. Furthermore, 7b could improve memory impairment induced by scopolamine, ethanol, and sodium nitrite using the step‐down passive avoidance task in vivo and could remarkably decrease the activity of acetylcholinesterase in mice brain. This study indicated that 7b could be considered as a potential multitarget agent against AD.

  DOI：

  10.1111/cbdd.12580

文献信息

• Synthesis of scutellarein derivatives to increase biological activity and water solubility
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Wei Zhang、Ze-Xi Dong、Yu-Ping Tang、Peng-Xuan Zhang、Ting Gu、Wen-Yu Wu、Fang Fang、Xin-Xue、He-Min Li、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1016/j.bmc.2015.09.047

  日期：2015.11

  In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease. (C) 2015 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Biological Evaluation of Scutellarein Carbamate Derivatives as Potential Multifunctional Agents for the Treatment of Alzheimer's Disease
  作者：Zhi-pei Sang、Xiao-ming Qiang、Yan Li、Bei Wu、Hui Zhang、Ming-gao Zhao、Yong Deng

  DOI：10.1111/cbdd.12580

  日期：2015.11

  A series of scutellarein carbamate derivatives were designed and synthesized based on the multitarget‐directed drug design strategy for treatment of Alzheimer's disease. Their acetylcholinesterase and butyrylcholinesterase inhibitory activities, antioxidant activities, metals chelation, and neuroprotective effects against hydrogen peroxide‐induced PC12 cell injury were evaluated in vitro. The preliminary results indicated that compound 7b exhibited good inhibitory potency toward AChE and BuChE with IC50 values of 1.2 ± 0.03 μm and 22.1 ± 0.15 μm, respectively, possessed the strong antioxidant potency (10.3 trolox equivalents), as well as acted as a selective metal chelator and neuroprotective agent. Furthermore, 7b could improve memory impairment induced by scopolamine, ethanol, and sodium nitrite using the step‐down passive avoidance task in vivo and could remarkably decrease the activity of acetylcholinesterase in mice brain. This study indicated that 7b could be considered as a potential multitarget agent against AD.
• Design, synthesis and biological evaluation of new multi-target scutellarein hybrids for treatment of Alzheimer’s disease
  作者：Keke Luo、Jiao Chen、Hui Li、Dirong Wu、Yuanjiang Du、Shanshan Zhao、Ting Liu、Li Li、Zeqin Dai、Yongjun Li、Yonglong Zhao、Lei Tang、Xiaozhong Fu

  DOI：10.1016/j.bioorg.2023.106596

  日期：2023.9
• Design, synthesis and evaluation of novel scutellarin and scutellarein-N,N-bis-substituted carbamate-l-amino acid derivatives as potential multifunctional therapeutics for Alzheimer’s disease
  作者：Dirong Wu、Jiao Chen、Keke Luo、Hui Li、Ting Liu、Li Li、Zeqin Dai、Yongjun Li、Yonglong Zhao、Xiaozhong Fu

  DOI：10.1016/j.bioorg.2022.105760

  日期：2022.5