3-fluoro-7-amino-4-methyl-2H-1-benzopyran-2-one | 1210052-30-4

• 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: 3-fluoro-7-amino-4-methyl-2H-1-benzopyran-2-one
• 英文别名: 7-Amino-3-fluoro-4-methylchromen-2-one
• CAS: 1210052-30-4
• 化学式: C₁₀H₈FNO₂
• 分子量: 193.177
• InChiKey: YZPWFNJBQJDFEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ac-Ile-Glu(tBu)-Thr(tBu)-Asp(tBu)-OH 、 3-fluoro-7-amino-4-methyl-2H-1-benzopyran-2-one 在 HATU 、 2,4,6-三叔丁基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成
  参考文献：
  名称：

  荧光半胱天冬酶8四肽底物的合成，酶评价和对接研究。

  摘要：

  描述了对半胱天冬酶8具有选择性的新型荧光基四肽底物的合成，酶学评估和分子模型研究，该底物具有一般结构Ac-IETD-AXX。von Pechmann缩合反应合成了各种荧光报告基团（AXX），即3和4个取代的香豆素和quinolin-2（1 H ）-1 。随后在新开发的合成条件下将它们与caspase-8选择性四肽Ac-IETD-OH偶联，以高收率和高对映体纯度提供所需的底物。基于K M和V max值，新化合物被证明是重组人caspase 8的优良底物。相反， K M与人半胱天冬酶3的底物相同的化合物的值大约高10–20倍。基于人半胱氨酸蛋白酶3和8的X射线晶体结构的分子建模研究表明，两个活性位点中都有足够的空间容纳在荧光香豆素和喹啉3和4位中具有中等体积取代基的底物。 2（1小时）-那些。使用程序AutoDock 3将底物自动对接至人胱天蛋白酶3和8的活性位点，其结构类似于已公开的晶体学结

  DOI：

  10.1002/cmdc.200900356
• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 硫酸 、 溶剂黄146 作用下， 生成 3-fluoro-7-amino-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

  摘要：

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.005

文献信息

• Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
  作者：Shu-Guang Zhang、Yu-Qiang Wan、Ya Wen、Wei-Hua Zhang

  DOI：10.3390/molecules27206904

  日期：——

  compounds have been used as fungicides for half a century, and dozens of varieties have been developed so far. This study focused on the introduction of carboxamide and sulfonamide moieties in a coumarin core to discover novel derivatives. Based on this strategy, we synthesized two series of novel carboxamide and sulfonamide substituted coumarin derivatives, and their fungicidal activity was also investigated

  香豆素类化合物具有抗肿瘤、抗凝血、抗HIV、抗真菌、杀虫等多种生物活性。酰胺类和磺胺类化合物作为杀菌剂已有半个世纪的历史，迄今已开发出几十个品种。这项研究的重点是在香豆素核心中引入羧酰胺和磺酰胺部分，以发现新的衍生物。基于此策略，我们合成了两个系列的新型羧酰胺和磺酰胺取代香豆素衍生物，并对其杀菌活性进行了研究。一些设计的化合物在初步试验中具有针对六种植物病原真菌的潜在活性，化合物6r突出显示。化合物6r表现出更强的杀真菌活性Botrytis cinerea (EC 50 = 20.52 µg/mL) 将成为进一步研究的主要结构。
• Device for enhancing fluorescence and kinetics and methods of using the device
  申请人：Becton Dickinson and Company

  公开号：EP0347771A2

  公开（公告）日：1989-12-27

  A carrier having at least one kinetics and fluorescence enhancing support and a dry substance selected from the group consisting of fluorogenic substrates, B-methylumbelliferone, 7-amino-4-methyl coumarin, B-napthylamine, fluoroscein, and resorufin deposited on the support demonstrates substantial enhancement of hydrolysis kinetics and fluorescence over pure liquid systems. When the device has a plurality of supports and the supports have different fluorogenic substrates an enzyme rate-of-reaction profile representative of a microorganism in the suspension can be determined and used to identify the organism. The device can also be used to characterize enzymes expressed by other biological specimens.

  一种载体具有至少一种动力学和荧光增强支持物，以及一种选自含氟底物、B-甲基伞形酮、7-氨基-4-甲基香豆素、B-萘胺、荧光素和resorufin 所组成的组的干物质，沉积在支持物上，与纯液体系统相比，该载体的水解动力学和荧光得到了极大的增强。当该装置具有多个支持物，且支持物具有不同的荧光底物时，可确定悬浮液中微生物的酶反应速率曲线，并用于识别该微生物。该装置还可用于鉴定其他生物样本表达的酶。
• Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents
  作者：Haonan Yu、Zhuang Hou、Ye Tian、Yanhua Mou、Chun Guo

  DOI：10.1016/j.ejmech.2018.04.005

  日期：2018.5

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Synthesis, Enzymatic Evaluation, and Docking Studies of Fluorogenic Caspase 8 Tetrapeptide Substrates
  作者：Przemysław Reszka、Riad Schulz、Karen Methling、Michael Lalk、Patrick J. Bednarski

  DOI：10.1002/cmdc.200900356

  日期：2010.1.4

  give the desired substrates in good yields and in high enantiomeric purity. Based on KM and Vmax values, the new compounds proved to be excellent substrates for recombinant human caspase 8. In contrast, the KM values for the same compounds as substrates for human caspase 3 were approximately 10–20‐fold higher. Molecular modeling studies based on the X‐ray crystal structures of both human caspases 3 and

  描述了对半胱天冬酶8具有选择性的新型荧光基四肽底物的合成，酶学评估和分子模型研究，该底物具有一般结构Ac-IETD-AXX。von Pechmann缩合反应合成了各种荧光报告基团（AXX），即3和4个取代的香豆素和quinolin-2（1 H ）-1 。随后在新开发的合成条件下将它们与caspase-8选择性四肽Ac-IETD-OH偶联，以高收率和高对映体纯度提供所需的底物。基于K M和V max值，新化合物被证明是重组人caspase 8的优良底物。相反， K M与人半胱天冬酶3的底物相同的化合物的值大约高10–20倍。基于人半胱氨酸蛋白酶3和8的X射线晶体结构的分子建模研究表明，两个活性位点中都有足够的空间容纳在荧光香豆素和喹啉3和4位中具有中等体积取代基的底物。 2（1小时）-那些。使用程序AutoDock 3将底物自动对接至人胱天蛋白酶3和8的活性位点，其结构类似于已公开的晶体学结