4-methyl-7-(phenylamino)-2H-chromen-2-one | 28821-12-7

• 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: 4-methyl-7-(phenylamino)-2H-chromen-2-one
• 英文别名: 7-phenylamino-4-methylcoumarin；7-anilino-4-methyl-2H-chromen-2-one；7-anilino-4-methylchromen-2-one
• CAS: 28821-12-7
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: OCAIEUHJBCIECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-methyl-2-oxochromen-7-yl)-N-phenylbenzamide 生成 4-methyl-7-(phenylamino)-2H-chromen-2-one
  参考文献：
  名称：

  SURENDRANATH V., SASMIRA TECHN. DIG., 1980, NO 3, 9-11

  摘要：

  DOI：

文献信息

• 4-Methyl-7-Amino/Amido Coumarin Derivatives as Potential Antimicrobials and Antioxidants
  作者：Muthipeedika Nibin Joy、Yadav D. Bodke、Sandeep Telkar

  DOI：10.1007/s10600-020-03106-y

  日期：2020.7

  An array of previously synthesized 4-methyl-7-amino and amido coumarins 4a–u has been screened for their antimicrobial and antioxidant properties. Some of the compounds exhibited promising antibacterial and antifungal activities (MIC ranging from 4–64 μg/mL) when compared to the respective standards. Compound 4u showed comparable antibacterial activity with the standard, ciprofloxacin, whereas compounds 4u and 4t displayed promising antifungal activity when compared to the standard, fluconazole. The in silico docking studies against gyrase enzyme revealed the fact that 4u possessed hydrogen bonding and significant hydrophobic interactions, which may be the reason for its superior antibacterial activity as compared to the other compounds. Compounds 4c and 4m showed comparable antioxidant activity with the standard, BHT, which can be attributed to the presence of electron-donating substituents.

  一批先前合成的4-甲基-7-氨基和酰胺香豆素4a–u已被筛选其抗菌和抗氧化性能。与各自的标准相比，一些化合物表现出有前景的抗菌和抗真菌活性（MIC范围为4-64 μg/mL）。化合物4u显示出与标准环丙沙星相当的抗菌活性，而化合物4u和4t在与标准氟康唑相比时显示出有前景的抗真菌活性。针对拓扑异构酶的计算对接研究揭示了4u具有氢键和显著的疏水相互作用，这可能是其相对于其他化合物具有更优越抗菌活性的原因。化合物4c和4m显示出与标准BHT相当的抗氧化活性，这可以归因于存在供电子取代基。
• A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K. K. Abdul Khader、M. Syed Ali Padusha、Ayyiliyath M. Sajith、A. Muralidharan

  DOI：10.1039/c4ra01720j

  日期：——

  A rapid approach for the synthesis of an array of 4-methyl-7-substituted coumarins has been developed.

  已开发出一种合成4-甲基-7-取代香豆素阵列的快速方法。
• Ground and excited states calculations of 7-phenylamino-substituted coumarins
  作者：Bo Xu、Jing Yang、Xuesong Jiang、Yuanlong Wang、Huai Sun、Jie Yin

  DOI：10.1016/j.molstruc.2008.06.020

  日期：2009.1

  A theoretical calculation of the ground and first excited states of two 7-phenylamino-substituted coumarin compounds are performed. In order to study the effect of phenyl substituted in amino group and fluorine atoms substituted in methyl group, 7-amino-4-methyl coumarin (C120) and 7-amino-4-(trifluoromethyl) coumarin (Cl 51) were also studied. The geometries of the ground state and the first ground state were optimized using density function theory and configuration interaction singles levels of theory. Molecular orbitals (MO) of the ground and first excited states of the four coumarin compounds were obtained to explain the change of the structures. ZINDO and TD-DFT methods with different basis sets were applied to predict the UV absorption spectra. The solvent effect had also been taken into account using self-consistent isodensity polarized continuum model. The predicted spectra are in agreement with the experimental data. Crown Copyright (c) 2008 Published by Elsevier B.V. All rights reserved.
• BHAVSAR M. D.; SURENDRANATH V., MAN-MADE TEXT. INDIA, 28,(1985) N 11, 425, 427-429, 431
  作者：BHAVSAR M. D.、 SURENDRANATH V.

  DOI：——

  日期：——
• SURENDRANATH V., SASMIRA TECHN. DIG., 1980, NO 3, 9-11
  作者：SURENDRANATH V.

  DOI：——

  日期：——