3-(3-(thiophene-2-yl)acryloyl)-2H-chromen-2-one

• 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-(3-(thiophene-2-yl)acryloyl)-2H-chromen-2-one
• 英文别名: 3-(3-Thiophen-2-ylprop-2-enoyl)chromen-2-one
• 化学式: C₁₆H₁₀O₃S
• 分子量: 282.32
• InChiKey: VQVMLZLOGBLZDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-(thiophene-2-yl)acryloyl)-2H-chromen-2-one 在 hydrazine hydrate 作用下， 反应 10.0h， 以73%的产率得到1-amino-3-(3-(thiophene-2-yl) acryloyl)quinoline-2(1H)-one
  参考文献：
  名称：

  Spectroscopic and Biophysical Studies on Chalcones and Schiff Bases Derived from Chromen-2-one and Quinoline-2(1H)-one Derivatives as Antibacterial Agents

  摘要：

  一系列由3-乙酰基香豆素合成的茶酮衍生物和芳基亚甲基类似物被合成。这些合成化合物通过元素分析、红外、1H和13C NMR以及质谱分析进行了阐明，然后这些合成化合物被纯化并对三种细菌菌株进行了测试。化合物9c对大肠杆菌和铜绿假单胞菌表现出高活性。化合物4和6a对大肠杆菌表现出中等活性，而化合物6a、6b和9c对金黄色葡萄球菌表现出中等活性。参考抗生素在相同条件下对相同的细菌菌株进行了测试，结果显示环丙沙星对铜绿假单胞菌和金黄色葡萄球菌具有正活性，但对大肠杆菌具有负活性，而阿莫西林对金黄色葡萄球菌具有正活性，但对大肠杆菌和铜绿假单胞菌具有负活性。另一方面，万古霉素对铜绿假单胞菌具有正活性，但未对大肠杆菌和金黄色葡萄球菌进行测试。化合物4和7对DNA断裂和DNA切割的金黄色葡萄球菌进行了处理。合成化合物9c的对接研究已确定，并与氨苄青霉素进行了比较。最后，还进行了合成化合物（3、4、6b、6c、6e、7、9c和9e）的UV和荧光分析。

  DOI：

  10.14233/ajchem.2020.22604
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 吡啶 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-(3-(thiophene-2-yl)acryloyl)-2H-chromen-2-one
  参考文献：
  名称：

  Spectroscopic and Biophysical Studies on Chalcones and Schiff Bases Derived from Chromen-2-one and Quinoline-2(1H)-one Derivatives as Antibacterial Agents

  摘要：

  一系列由3-乙酰基香豆素合成的茶酮衍生物和芳基亚甲基类似物被合成。这些合成化合物通过元素分析、红外、1H和13C NMR以及质谱分析进行了阐明，然后这些合成化合物被纯化并对三种细菌菌株进行了测试。化合物9c对大肠杆菌和铜绿假单胞菌表现出高活性。化合物4和6a对大肠杆菌表现出中等活性，而化合物6a、6b和9c对金黄色葡萄球菌表现出中等活性。参考抗生素在相同条件下对相同的细菌菌株进行了测试，结果显示环丙沙星对铜绿假单胞菌和金黄色葡萄球菌具有正活性，但对大肠杆菌具有负活性，而阿莫西林对金黄色葡萄球菌具有正活性，但对大肠杆菌和铜绿假单胞菌具有负活性。另一方面，万古霉素对铜绿假单胞菌具有正活性，但未对大肠杆菌和金黄色葡萄球菌进行测试。化合物4和7对DNA断裂和DNA切割的金黄色葡萄球菌进行了处理。合成化合物9c的对接研究已确定，并与氨苄青霉素进行了比较。最后，还进行了合成化合物（3、4、6b、6c、6e、7、9c和9e）的UV和荧光分析。

  DOI：

  10.14233/ajchem.2020.22604

文献信息

• Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities
  作者：Nosrat O. Mahmoodi、Shahryar Ghodsi

  DOI：10.1007/s11164-016-2644-2

  日期：2017.2

  Abstract A series of novel 3-(2-oxo-2H-chromen-3-yl)-1-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-5-aryl-1H-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction are the incorporation of four heterocyclic rings in the structure of target products, using commonly

  摘要 一系列新颖的3-（2-oxo-2 H -chromen-3-yl）-1-（4-（2-oxo-2 H -chromen-3-yl）thiazol-2-yl）-5-芳基-1高通过各种香豆素查尔酮，硫代氨基脲和2-溴香豆素的一锅式三组分环缩合反应制得了-吡唑-1-溴化溴化物。该反应的关键特征是使用通常可得的和廉价的催化剂，在目标产物的结构中引入四个杂环，高收率和简单的反应条件。最终的盐产物是通过吡唑部分的氮原子对质子的自捕获而获得的。简便的后处理和温和的反应条件是该方案的显着特征。检查了合成产品的抗氧化，抗菌和抗真菌活性。与参考文献相比，大多数化合物显示出良好的生物学能力。 图形概要
• Synthesis, In Silico Studies, and Larvicidal Activity of Novel Hydrazinyl 1,3-Thiazine Derivatives
  作者：Amarnath Velidandi、Rajeswari Kannuri、Murali Krishna Thupurani

  DOI：10.1134/s1070428022060094

  日期：2022.6

  Abstract Looking at the importance of thiazine derivatives as biologically active compounds, herein we describe the synthesis of 4,6-diaryl-2-hydrazinyl-1,3-thiazines from the corresponding chalcones and thiosemi­carbazide in the presence of sodium hydroxide on heating. The synthesized compounds were tested for their larvicidal activity against saltwater shrimp eggs (Artemia cysts), and some of the

  摘要 鉴于噻嗪衍生物作为生物活性化合物的重要性，本文描述了在氢氧化钠存在下加热时由相应的查尔酮和氨基硫脲合成 4,6-二芳基-2-肼基-1,3-噻嗪。测试了合成的化合物对咸水虾卵（卤虫孢囊）的杀幼虫活性，其中一些化合物表现出良好至优异的活性。估计了它们在计算机上的药物相似性。
• Synthesis and Optical Properties Research of Some Novel Trichromophore Compounds Containing Coumarin, Pyrazoline and Naphthalimide Groups
  作者：Hu Shengli、Wu Gongying、Zhao Fang、Hu Yang

  DOI：10.3987/com-16-13613

  日期：——

  A series of novel trichromophore compounds containing coumarin, pyrazoline and naphthalimide groups were synthesized and their properties were elucidated using absorption and fluorescence. In chloroform solution, their maximal absorption bands and the maximal emission bands slightly varied from 478 to 485 nm and from 559 to 565 nm, respectively.
• Antidiabetic effect of novel benzenesulfonylureas as PPAR-γ agonists and their anticancer effect
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Abhijeet Dhulap、Sameena Bano、Yakub Ali

  DOI：10.1016/j.bmcl.2015.08.062

  日期：2015.10

  Twenty one pyrazoline containing benzenesulfonylureas were synthesized and docked against PPAR-gamma target. All the compounds were first screened for their antidiabetic potential by oral glucose tolerance test and then six active compounds were assessed on STZ diabetic model. It was found that five compounds showed significantly high antidiabetic activity in comparison to glibenclamide as well as rosiglitazone (standard drugs). The active compounds were evaluated for their effect on body weight since weight management is one of the main concerns associated with sulfonylureas. Finally, the most active compound 6f was shown to elevate PPAR-gamma gene expression. The synthesized compounds were also screened for anticancer activity by National Cancer Institute. Five compounds (5i, 6e, 6g, 6i and 6j) were selected at one dose level and showed potency against cancers. (C) 2015 Elsevier Ltd. All rights reserved.
• Spectroscopic and Biophysical Studies on Chalcones and Schiff Bases Derived from Chromen-2-one and Quinoline-2(1H)-one Derivatives as Antibacterial Agents
  作者：Saad H. Alotaibi

  DOI：10.14233/ajchem.2020.22604

  日期：——

  A series of chalcone derivatives and arylidene analogues derived from 3-acetyl coumarin were synthesized. The synthesized compounds were elucidated by spectroscopic analysis such as elemental analysis, infrared, 1H & 13C NMR and mass spectroscopies, and then the synthesized compounds were purified and tested against three bacterial strains. Compound 9c showed high activity against E. coli and P. aeruginosa. Compounds 4 and 6a showed moderate activity against E. coli while compounds 6a, 6b and 9c showed moderate activity against S. aureus. The reference antibiotics were tested against the same bacteria strains in the same conditions and showed that ciprofloxacin have positive activity against P. aeruginosa and S. aureus but it shows negative activity against E. coli while amoxicillin have positive activity against S. aureus and negative activity against E. coli and P. aeruginosa. On the other hand, vancomycin has positive activity against P. aeruginosa but not tested against E. coli and S. aureus. Staph strains were treated with compounds 4 and 7 on DNA fragmentation and DNA cleavage. Docking studies of synthesized compound 9c was determined and the results were compared with ampicillin. Finally, UV and fluorescence analyses of the synthesized compounds (3, 4, 6b, 6c, 6e, 7, 9c and 9e) were also conducted.

  一系列由3-乙酰基香豆素合成的茶酮衍生物和芳基亚甲基类似物被合成。这些合成化合物通过元素分析、红外、1H和13C NMR以及质谱分析进行了阐明，然后这些合成化合物被纯化并对三种细菌菌株进行了测试。化合物9c对大肠杆菌和铜绿假单胞菌表现出高活性。化合物4和6a对大肠杆菌表现出中等活性，而化合物6a、6b和9c对金黄色葡萄球菌表现出中等活性。参考抗生素在相同条件下对相同的细菌菌株进行了测试，结果显示环丙沙星对铜绿假单胞菌和金黄色葡萄球菌具有正活性，但对大肠杆菌具有负活性，而阿莫西林对金黄色葡萄球菌具有正活性，但对大肠杆菌和铜绿假单胞菌具有负活性。另一方面，万古霉素对铜绿假单胞菌具有正活性，但未对大肠杆菌和金黄色葡萄球菌进行测试。化合物4和7对DNA断裂和DNA切割的金黄色葡萄球菌进行了处理。合成化合物9c的对接研究已确定，并与氨苄青霉素进行了比较。最后，还进行了合成化合物（3、4、6b、6c、6e、7、9c和9e）的UV和荧光分析。