8-methy-4-chlorocoumarin | 51069-77-3

• 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: 8-methy-4-chlorocoumarin
• 英文别名: 4-chloro-8-methyl-2H-chromen-2-one；4-Chloro-8-methylcoumarin；4-chloro-8-methylchromen-2-one
• CAS: 51069-77-3
• 化学式: C₁₀H₇ClO₂
• 分子量: 194.617
• InChiKey: MCARILAYIVECBU-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methy-4-chlorocoumarin 在 铜 、 三乙胺 、 copper(l) chloride 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 7-(4-Methoxy-phenylamino)-4-methyl-chromeno[4,3-b]quinolin-6-one
  参考文献：
  名称：

  Mulwad; Mahaddalkar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 1, p. 29 - 32

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 反应 3.0h， 生成 8-methy-4-chlorocoumarin
  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

• Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents
  作者：Qinggang Ji、Zhiqiang Ge、Zhixing Ge、Kaizhi Chen、Hualong Wu、Xiaofei Liu、Yanrong Huang、Lvjiang Yuan、Xiaolan Yang、Fei Liao

  DOI：10.1016/j.ejmech.2015.11.027

  日期：2016.1

  A series of novel phosphoramidate derivatives of coumarin have been designed and synthesized as chitin synthase (CHS) inhibitors. All the synthesized compounds have been screened for their chitin synthase inhibition activity and antimicrobial activity in vitro. The bioactive assay manifested that most of the target compounds exhibited good efficacy against CHS and a variety of clinically important fungal pathogens. In particular, compound 7t with IC50 of 0.08 mM against CHS displayed stronger efficiency than the reference Polyoxin B with IC50 of 0.16 mM. In addition, the apparent Ki values of compound 7t was 0.096 mM while the K-m of Chitin synthase prepared from Candida tropicalis was 3.86 mM for UDP-N-acetylglucosamine, and the result of the K-i showed that the compounds was a non-competitive inhibitor of the CHS. As far as the antifungal activity is concerned, compounds 7o, 7r and 7t were highly active against Aspergillus flavus with MIC values in the range of 1 p,g/mL to 2 mu g/MI while the results of antibacterial screening showed that these compounds have negligible actions to the tested bacteria. These results indicated that the design of these compounds as antifungal agents was rational. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Studies of bioactive heterocycles: amino Claisen rearrangement of 4-N-(4-aryloxybut-2-ynyl),N-methylaminocoumarins
  作者：K.C Majumdar、T Bhattacharyya

  DOI：10.1016/s0040-4039(01)00656-6

  日期：2001.6

  Thermal amino-Claisen rearrangement of 4-N-(aryloxybut-2-ynyl), N-methyl-aminocoumarins (8a-e) in refluxing o-dichlorobenzene gave 4-aryloxymethylene-1-methyl-1,2,3-trihydropyrido[3,2-c][1]benzopyran-5-ones (9a-e) in 56-72% isolated yields. Substrates (8a-f) were prepared from 4-chlorocoumarin (6a,b) and N-(4-ary-loxybutynyl),N-methylamine (7a-f) in 68-77% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.