2H-1-苯并吡喃-2-酮,3-[1-(苯基亚肼基)乙基]- | 103593-74-4

• 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
• 中文名称: 2H-1-苯并吡喃-2-酮,3-[1-(苯基亚肼基)乙基]-
• 英文名称: 3-[1-(phenylhydrazono)ethyl]chromen-2-one
• 英文别名: 3-(1-(2-phenylhydrazono)ethyl)-2H-chromen-2-one；2H-1-Benzopyran-2-one, 3-[1-(phenylhydrazono)ethyl]-；3-(N-anilino-C-methylcarbonimidoyl)chromen-2-one
• CAS: 103593-74-4
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: KEJFBZOKPJYFPN-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C(Solv: ethanol (64-17-5))
• 沸点：
  465.9±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2H-1-苯并吡喃-2-酮,3-[1-(苯基亚肼基)乙基]- 在 甲烷磺酸 、 四磷十氧化物 作用下， 生成 2-(2-oxobenzopyran-3-yl)indole
  参考文献：
  名称：

  Some new indole–coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies

  摘要：

  Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.10.001
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 溶剂黄146 作用下， 反应 1.0h， 生成 2H-1-苯并吡喃-2-酮,3-[1-(苯基亚肼基)乙基]-
  参考文献：
  名称：

  某些香豆素杂化物作为选择性碳酸酐酶IX和XII抑制剂的合成和生物学评估。

  摘要：

  合成了两个系列，通过吡唑接头与香豆素相连的噻唑烷酮（系列1a-m）和与香豆素相连的1,2,3-三唑（系列5a-j，系列2），对合成的化合物进行了抗四种生理和药理相关的hCA亚型，即hCA I，II，IX和XII。结果表明，与脱靶同工型hCA I和II相比，肿瘤相关同工型hCA IX和XII具有选择性抑制作用。与hCA XII相比，系列1的化合物表现出更好的hCA IX抑制，其中化合物6i，6h，6a和6k的K i值小于100 nM。在所有化合物中，化合物6i表现出最佳的抑制作用，K i值为61.5 nM。在系列2的化合物中，化合物5a，5b，5c，5d，5f和5j显示出显着的hCA IX抑制。化合物5d表现出最佳的抑制作用，K i值为32.7 nM。在hCA XII的情况下，化合物5i表现出最佳抑制作用，K i值为84.2 nM。因此，可以将系列1的化合物6i和系列2的5d用作进一步开发选择性和有效hCA

  DOI：

  10.1016/j.bioorg.2020.104272

文献信息

• Synthesis of novel substituted 3-(4-((1H-benzo[d]imidazol-2-ylthio)methyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-ones: various approaches
  作者：Devulapally Srikrishna、Pramod Kumar Dubey

  DOI：10.1007/s11164-018-3397-x

  日期：2018.7

  a privileged structure for developing probes of impressive pharmacological potentials, some new coumarin and pyrazole conjugates of benzimidazoles were synthesized with a sulphur linkage. Thus, 3-(2-oxo-2 H -chromen-3-yl)-1-phenyl-1 H -pyrazole-4-carbaldehyde ( 3 ) was prepared starting from simple salicylaldehyde which has been used as an important synthon and incorporated in a series of structural

  摘要以 苯并咪唑为优先结构，可开发出令人印象深刻的药理潜力的探针，合成了一些新的具有硫键的苯并咪唑香豆素和吡唑共轭物。因此，3-（2-氧代-2- ħ -苯并吡喃-3-基）-1-苯基-1- ħ 吡唑-4-甲醛（ 3 ）的制备从已经作为重要的合成子和并入简单水杨醛开始在一系列结构操作中获得各种药效基序缀合物 9（a–b） 和 13（a–f） ，以合理的收益率。我们已经开发出了简便且逐步的方法，可以通过各种方法合成所有这些化合物，其中还涉及子序列。通过IR，1 HNMR，13 CNMR和质谱数据很好地表征了所有合成的化合物。 图形概要
• Synthesis of Some Hippuric Acid Substrate Linked Novel Pyrazoles as Antimicrobial Agents
  作者：Anil Verma、Vinod Kumar、Rajshree Khare、Joginder Singh

  DOI：10.14233/ajchem.2019.21671

  日期：——

  Escalating resistance of microorganisms to the currently accessible antimicrobial drugs has forced to synthesize some novel biologically active compounds as efficient alternates via economical substrates. Hence, hippuric acid was used as one of the starting materials to synthesize pyrazole derivatives. All the synthesized compounds were characterized by IR, NMR (1H & 13C) and mass spectral data. The antimicrobial potential of synthesized compounds has been explored against four bacterial and two fungal strains. Among the 12 compounds, 3 compounds 8j, 8k and 8l were found to exhibit prominent antimicrobial potential as compared with the standards ciprofloxacin and amphotericin-B.

  微生物对目前可获得的抗微生物药物逐渐产生抗药性，迫使合成一些新型生物活性化合物作为有效的替代品，通过经济实惠的底物。因此，苯乙酰甲酸被用作合成吡唑衍生物的起始物质之一。所有合成的化合物均通过红外光谱、核磁共振（1H和13C）和质谱数据进行表征。合成化合物的抗微生物潜力已针对四种细菌和两种真菌菌株进行探索。在12种化合物中，化合物8j、8k和8l与标准药物环丙沙星和两性霉素B相比，显示出明显的抗微生物潜力。
• 3-(1-Phenyl-4-((2-(4-arylthiazol-2-yl)hydrazono)methyl)-1H-pyrazol-3-yl)-2H-chromen-2-ones: one-pot three component condensation, in vitro antimicrobial, antioxidant and molecular docking studies
  作者：Ramesh Gondru、Janardhan Banothu、Ranjith Kumar Thatipamula、Althaf Hussain SK、Rajitha Bavantula

  DOI：10.1039/c5ra04196a

  日期：——

  evaluated for their in vitro antimicrobial and antioxidant activities. Among the tested compounds (5a–l), the derivatives 5k, 5h and 5a have displayed broad spectrum antibacterial activity, whereas the compounds 5b and 5f were found to be potent antifungal agents. Antioxidant activity results revealed that compounds 5a, 5b and 5i exhibited higher radical scavenging ability than the positive control drug

  为了找到一类新型的杂环生物活性剂，一系列新颖的3-（1-苯基-4-（（2-（4-芳基噻唑-2-基）肼基）甲基）-1 H-吡唑通过Hantzsch缩合反应，通过三组分一锅法有效地定量和定性合成了-3-yl）-2 H -chromen-2-one衍生物（5a-1）。通过光谱数据和元素分析确定了所有新合成化合物的结构，并对其体外抗菌和抗氧化活性进行了评估。在测试化合物（5a–l）中，衍生物5k，5h和5a已经显示出广谱的抗菌活性，而发现化合物5b和5f是有效的抗真菌剂。抗氧化活性结果表明，化合物5a，5b和5i的清除自由基能力高于阳性对照药物Trolax。此外，将合成化合物（5a–l）分子对接至大肠杆菌晶体结构的结合位点MurB酶（PDB ID：1MBT）是肽聚糖生物合成中的关键酶，用于全面了解可能的结合方式，并比较这些化合物的理论和实验结果。对接结果表明，配体的对接分数和H键相互作用与体外结果
• An efficient multichannel probe to detect anions in different media and its real application in human blood plasma
  作者：Syed S. Razi、Rashid Ali、Priyanka Srivastava、Mohammad Shahid、Arvind Misra

  DOI：10.1039/c4ra02388a

  日期：——

  A simple coumarin derived chromo and fluorogenic chemosensor has been synthesized and tested to detect anions in different medium. The designed chemosensor has shown a high colorimetric response for F− and AcO− ions in acetonitrile in which the color of solution changed from a yellow-green to red and orange respectively whereas, in aqueous medium the probe showed high fluorogenic response and selectively reacted with cyanide through a Michael type nucleophilic addition reaction in which a nonfluorescent (switched-off) color of the solution, “turn-on” to became fluorescent blue (switched-on). The multichannel mode of interaction between the probe and anions has been confirmed by absorption, emission, FT-IR, NMR, ESI-MS spectral data analysis. Moreover, the probe has shown high sensitivity to detect cyanide in a real sample, human blood plasma as well as on paper strips.

  我们合成并测试了一种简单的香豆素衍生色荧光化学传感器，用于检测不同介质中的阴离子。所设计的化学传感器对乙腈中的 F- 和 AcO- 离子显示出很高的比色反应，溶液的颜色分别从黄绿色变为红色和橙色；而在水介质中，探针显示出很高的荧光反应，并通过迈克尔型亲核加成反应与氰化物发生选择性反应，溶液的非荧光颜色（关闭）"打开"，变成荧光蓝色（打开）。探针与阴离子之间的多通道相互作用模式已通过吸收、发射、傅立叶变换红外光谱、核磁共振、ESI-MS 光谱数据分析得到证实。此外，该探针在实际样品、人体血浆和纸条中检测氰化物时显示出极高的灵敏度。
• Potassium Carbonate–Mediated Efficient and Convenient Synthesis of 3-Methyl-1-phenylchromeno[4,3-<i>c</i>]pyrazol-4(1<i>H</i>)-ones
  作者：Jagdeep Grover、Somendu Kumar Roy、Sanjay Madhukar Jachak

  DOI：10.1080/00397911.2013.879184

  日期：2014.7.3

  Abstract Unprecedented cyclization was observed during N-sulfonylation of 3-[1-(phenylhydrazono)-ethyl]-chromen-2-one in pyridine, affording 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones. To avoid use of noxious pyridine, reaction was tried in different basic conditions and the best results were obtained with potassium carbonate in acetone. A wide range of substrates bearing either electron-donating

  摘要 3-[1-(苯肼基)-乙基]-chromen-2-one 在吡啶中的 N-磺酰化过程中观察到前所未有的环化反应，得到 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H ）-那些。为了避免使用有毒的吡啶，在不同的碱性条件下尝试了反应，并在丙酮中使用碳酸钾获得了最好的结果。在苯肼环上带有给电子或吸电子取代基的各种底物都与所开发的方法兼容。起始原料 3-乙酰香豆素的快速获取、产物的优异收率以及使用环境友好的碱和溶剂进行环化使该策略成为合成 3-甲基-1-苯基色基[4,3-c] 的一种高效便捷的方法]吡唑-4(1H)-酮。图形概要