N-(4-methoxyphenyl)-2-[(2-oxo-2H-chromen-7-yl)oxy]acetamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(4-methoxyphenyl)-2-[(2-oxo-2H-chromen-7-yl)oxy]acetamide
• 英文别名: N-(4-methoxyphenyl)-2-(2-oxo-2H-chromen-7-yloxy)acetamide；N-(4-methoxyphenyl)-2-(2-oxochromen-7-yl)oxyacetamide
• 化学式: C₁₈H₁₅NO₅
• mdl: MFCD03483693
• 分子量: 325.321
• InChiKey: MWUAZNQPGOXHCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-[2-(4-methoxyphenyl)-2-oxoethoxy]-2H-chromen-2-one 在 硫酸 、 sodium azide 作用下， 反应 1.17h， 以66%的产率得到N-(4-methoxyphenyl)-2-[(2-oxo-2H-chromen-7-yl)oxy]acetamide
  参考文献：
  名称：

  Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model

  摘要：

  We have designed and synthesized certain novel oxime- and amide-bearing coumarin derivatives as nuclear factor erythroid 2 p45-related factor 2 (Nrf2) activators. The potency of these compounds was measured by antioxidant responsive element (ARE)-driven luciferase activity, level of Nrf2-related cytoprotective genes and proteins, and antioxidant activity. Among them, (Z)-3-(2-(hydroxyimino)-2-phenylethoxy)-2H-chromen-2-one (17a) was the most active, and more potent than the positive t-BHQ in the induction of ARE-driven luciferase activity. Exposure of HSC-3 cells to various concentrations of 17a strongly increased Nrf2 nuclear translocation and the expression level of Nrf2-mediated cytoprotective proteins in a concentration-dependent manner. HSC-3 cells pretreated with 17a significantly reduced t-BOOH-induced oxidative stress. In the animal experiment, Nrf2-mediated cytoprotective proteins, such as aldo-keto reductase 1 subunit C-1 (AKR1C1), glutathione reductase (GR), and heme oxygenase (HO-1), were obviously elevated in the liver of 17a-treated mice than that of control. These results suggested that novel oxime-bearing coumarin 17a is able to activate Nrf2/ARE pathway in vivo and are therefore seen as a promising candidate for further investigation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.029

文献信息

• COMPOUNDS FOR TREATING INFECTIOUS DISEASES
  申请人：Whatehead Institute for Biomedical Research

  公开号：US20150284356A1

  公开（公告）日：2015-10-08

  The present invention provides compounds of Formula I, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting fungal or parasitic growth. The compounds are useful as inhibitors of glycosylphosphatidylinositol (GPI)-anchor biosynthesis, in particular, as inhibitors of fungal Gwt1 activity. The present invention further provides methods of using the compounds described herein for treating fungal or parasitic infections. The compounds can also be used as biological probes to study the effects of inhibiting Gwt1 activity.

  本发明提供了式I的化合物，其药用盐以及药物组合物。本发明的化合物对抑制真菌或寄生虫生长有用。这些化合物可用作糖基磷脂酰肌醇（GPI）锚定生物合成的抑制剂，特别是作为真菌Gwt1活性的抑制剂。本发明还提供了利用本文所述化合物治疗真菌或寄生虫感染的方法。这些化合物还可用作生物探针，用于研究抑制Gwt1活性的影响。
• Coumarin and 3,4-dihydroquinolinone derivatives: Synthesis, antidepressant activity, and molecular docking studies
  作者：Shi-Ben Wang、Hui Liu、Guang-Yong Li、Jun Li、Xiao-Jing Li、Kang Lei、Li-Chao Wei、Zhe-Shan Quan、Xue-Kun Wang、Ren-Min Liu

  DOI：10.1016/j.pharep.2019.07.011

  日期：2019.12

  (Compounds 8, 9, 11, 14, 15, 18-20, 23, 24 and 28 are new compounds) and studied their antidepressant activities. METHODS Forced swimming test (FST) and tail suspension test (TST) were used to evaluate the antidepressant activity of the target compounds. The most active compound was used to evaluate the exploratory activity of the animals by the open-field test. 5-HT concentration was estimated to evaluate

  背景香豆素和3,4-二氢喹啉酮核是两个重要的杂环，并广泛用于生物活性分子的开发。在这里，我们设计并合成了一系列3,4-二氢喹啉酮和香豆素衍生物（化合物8、9、11、14、15、18-20、23、24和28为新化合物）并研究了它们的抗抑郁活性。方法采用强迫游泳试验(FST)和悬尾试验(TST)评价目标化合物的抗抑郁活性。最活跃的化合物用于通过旷场测试评估动物的探索活动。通过使用 ELISA 估算 5-HT 浓度，以评估该化合物是否对小鼠大脑有影响。还进行了 5-HT1A 结合测定。通过分子对接研究验证了化合物的生物活性。Discovery Studio 和 ChemBioDraw Ultra 预测了目标化合物的理化和药代动力学特性。结果 在所有测试的化合物中，化合物7表现出最好的抗抑郁活性，其在FST中使不动时间减少了65.52 s。然而，在旷场试验中，化合物7并不影响自发活动。体内5-HT
• INHIBITORS OF PLASMODIUM FALCIPARUM EQUILIBRATIVE NUCLEOSIDE TRANSPORTER TYPE I AS ANTI-PARASITIC COMPOUNDS
  申请人：TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20160122362A1

  公开（公告）日：2016-05-05

  Inhibitors of Plasmodium falciparum equilibrative nucleoside transporter type 1 are identified and methods of use as anti-parasitic compounds are provided.
• US9505735B2
  申请人：——

  公开号：US9505735B2

  公开（公告）日：2016-11-29
• US9695193B2
  申请人：——

  公开号：US9695193B2

  公开（公告）日：2017-07-04