4-(phenylamino)-8-methyl-2H-chromen-2-one | 1258700-55-8

• 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-(phenylamino)-8-methyl-2H-chromen-2-one
• 英文别名: 4-Anilino-8-methylchromen-2-one
• CAS: 1258700-55-8
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: KCLMIXMWWIRNCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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

• 作为反应物：
  描述：

  聚合甲醛 、 4-(phenylamino)-8-methyl-2H-chromen-2-one 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 16.0h， 以78%的产率得到7-methyl-1-phenyl-1,4-dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-one
  参考文献：
  名称：

  Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins

  摘要：

  一种简便的方法用于将4-氨基香豆素经H2SO4介导的羟甲基化/环化N,O-缩醛化反应转化为1,4-二氢-2H,5H-色诺[4,3-d][1,3]噁唑啉-5-酮，产率中等至良好，已经开发并优化。还研究了该转化的范围和限制，该反应发生在水或水/THF混合物中。所得三环化合物的氮原子用于连接烷基、芳基和1,2,3-三唑基甲基基团，对后者采用两步点击化学方法。还研究了杂环化合物以及它们的1,2,3-三唑衍生物的光物理性质。N-芳基衍生物表现出高量子产率的荧光（高达Φf = 0.69）和非常大的斯托克斯位移（高达201 nm）。

  DOI：

  10.1055/s-0037-1612428
• 作为产物：
  描述：

  邻甲酚 在 三乙胺 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 4-(phenylamino)-8-methyl-2H-chromen-2-one
  参考文献：
  名称：

  4取代香豆素的合成，细胞毒性评估和计算机模拟研究

  摘要：

  合成了两个在第4位具有苯胺和杂环的香豆素，并在MTT分析中评估了它们对MCF-7癌细胞的体外细胞毒活性。结构活性关系（SAR）研究表明，香豆素第8位的电子供体基团在细胞毒性活性中起着重要作用。化合物VIId显示出强大的细胞毒活性，其次是化合物Xa，IC 50分别 为6.25和6.50μM。还对最有效的化合物进行了对接研究，以深入了解与NF-κB蛋白p50亚基的分子相互作用。

  DOI：

  10.1002/jhet.2458

文献信息

• Screening for In Vitro Antimycobacterial Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-(arylamino)coumarin Derivatives
  作者：Vijay Virsdoia、Mushtaque S. Shaikh、Atul Manvar、Bhavik Desai、Alpesh Parecha、Raju Loriya、Kinnari Dholariya、Gautam Patel、Vipul Vora、Kuldip Upadhyay、Karia Denish、Anamik Shah、Evans C. Coutinho

  DOI：10.1111/j.1747-0285.2010.00997.x

  日期：2010.11

  The resurgence of tuberculosis and the emergence of multidrug‐resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We have synthesized a small library of 50 analogues of 4‐(arylamino)coumarins with various aromatic amines at the C4‐ position of the coumarin scaffold. The compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv with rifampicin as the standard. Of the molecules synthesized, compound 9 was found to be most potent with a minimum inhibitory concentration >6.25 μg/mL for 100% inhibition. In an effort to develop new and more effective molecules in this series, the relationship between structure and activity was investigated by comparative molecular field analysis. Various models were generated using comparative molecular field analysis alone and comparative molecular field analysis plus a hydropathy field (HINT). In all, eight models were generated with atom‐fit and field‐fit alignment strategies. The comparative molecular field analysis models (Models 3a and 4a) based on field‐fit alignment were the best with statistically good correlation coefficients (r2) and cross‐validated q2. The values of r2pred for the validation set were 0.469 and 0.516. Based on the comparative molecular field analysis contours, some insights into the structure–activity relationship of the compounds could be gained.
• Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins
  作者：Marina C. Dilelio、Nathan P. Brites、Larissa A. Vieira、Bernardo A. Iglesias、Teodoro S. Kaufman、Claudio C. Silveira

  DOI：10.1055/s-0037-1612428

  日期：2019.8

  A facile protocol for the unprecedented one-pot H2SO4-mediated hydroxymethylation/cyclative N,O-acetalization of 4-aminocoumarins to 1,4-dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, in moderate to good yields, was developed and optimized. The scope and limitations of the transformation, which takes place in water or water/THF mixtures, were also studied. The nitrogen atom of the resulting tricycles was used to tether alkyl, aryl and 1,2,3-triazolylmethyl moieties, employing a two-step click chemistry approach for the latter. The photophysical properties of the heterocycles, as well as of their 1,2,3-triazole derivatives, were also examined. The N-aryl derivatives exhibited high quantum yields of fluorescence (up to Φf = 0.69) and very large Stokes shifts (up to 201 nm).

  一种简便的方法用于将4-氨基香豆素经H2SO4介导的羟甲基化/环化N,O-缩醛化反应转化为1,4-二氢-2H,5H-色诺[4,3-d][1,3]噁唑啉-5-酮，产率中等至良好，已经开发并优化。还研究了该转化的范围和限制，该反应发生在水或水/THF混合物中。所得三环化合物的氮原子用于连接烷基、芳基和1,2,3-三唑基甲基基团，对后者采用两步点击化学方法。还研究了杂环化合物以及它们的1,2,3-三唑衍生物的光物理性质。N-芳基衍生物表现出高量子产率的荧光（高达Φf = 0.69）和非常大的斯托克斯位移（高达201 nm）。
• Synthesis, Cytotoxic Evaluation, and<i>In Silico</i>Studies of 4-Substituted Coumarins
  作者：Prabhjot Kaur、Rupinder Kaur Gill、Gagandip Singh、Jitender Bariwal

  DOI：10.1002/jhet.2458

  日期：2016.9

  series of coumarins possessing the aniline‐ and heterocyclic ring at 4th position have been synthesized and evaluated for their in vitro cytotoxic activity against MCF‐7 cancer cell line in MTT assay. Structure activity relationship (SAR) studies reveal that the electron donor group at position‐8 of coumarin played an important role in cytotoxic activity. Compound VIId showed the potent cytotoxic activity

  合成了两个在第4位具有苯胺和杂环的香豆素，并在MTT分析中评估了它们对MCF-7癌细胞的体外细胞毒活性。结构活性关系（SAR）研究表明，香豆素第8位的电子供体基团在细胞毒性活性中起着重要作用。化合物VIId显示出强大的细胞毒活性，其次是化合物Xa，IC 50分别 为6.25和6.50μM。还对最有效的化合物进行了对接研究，以深入了解与NF-κB蛋白p50亚基的分子相互作用。