6-Acetyl-7-hydroxy-4,8-dimethylcoumarin | 13368-09-7

• 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: 6-Acetyl-7-hydroxy-4,8-dimethylcoumarin
• 英文别名: 6-acetyl-7-hydroxy-4,8-dimethyl-2H-chromen-2-one；6-acetyl-7-hydroxy-4,8-dimethylchromen-2-one
• CAS: 13368-09-7
• 化学式: C₁₃H₁₂O₄
• mdl: MFCD01106612
• 分子量: 232.236
• InChiKey: ZHNUBTVEXMINJU-UHFFFAOYSA-N

物化性质

• 熔点：
  192-193 °C
• 沸点：
  442.9±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Acetyl-7-hydroxy-4,8-dimethylcoumarin 在 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 7-hydroxy-4,8-dimethyl-6-(1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and anticancer activity of 6-heteroarylcoumarins

  摘要：

  A series of novel 7-hydroxy-8-methyl-coumarins with indole, pyrimidine, pyrazole, pyran, tetrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazol, 2-oxo-1,2-dihydropyridine and dihydropyrazolo[3,4-b]pyridine moieties at C6 position of heterocyclic core have been synthesized. Anticancer activity screening on NCI60 cell lines allowed identification of 6-(6-fluoro-1H-indo1-2-yl)-7-hydroxy-4,8-dimethy1-2H-chromen-2-one (23) with the highest level of antimitotic activity with mean GI(50)/TGI values of 3.28/13.24 mu M and certain sensitivity profile towards the Non-Small Cell Lung Cancer cell line HOP-92 (GI(50)/TGI/LC50 values 0.95/4.17/29.9 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.021
• 作为产物：
  描述：

  7-羟基-4,8-二甲基香豆素 在 三氯化铝 、 sodium acetate 作用下， 生成 6-Acetyl-7-hydroxy-4,8-dimethylcoumarin
  参考文献：
  名称：

  Rangaswami; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1938, # 7, p. 8,10

  摘要：

  DOI：

文献信息

• A Novel Approach to Sulfide Derivatives of Furocoumarin Natural Products
  作者：Michael A. Abramov、Wim Dehaen

  DOI：10.1055/s-2000-7609

  日期：——

  A new method for the preparation of derivatives of furocoumarin natural products is described. The 6(8)-(1,2,3-thiadiazol-4-yl)-7-hydroxycoumarins smoothly transform into 2-alkylthio angelicin and psoralen derivatives through base catalyzed thiadiazole ring cleavage and subsequent furan ring closure.

  介绍了一种制备呋喃香豆素天然产物衍生物的新方法。 6(8)-(1,2,3-噻二唑-4-基)-7-羟基香豆素通过碱催化噻二唑环裂解和随后的呋喃环闭合顺利转化为2-烷硫基当归素和补骨脂素衍生物。
• Synthesis and evaluation of chromenyl barbiturates and thiobarbiturates as potential antitubercular agents
  作者：S. Vijaya Laxmi、Y. Thirupathi Reddy、B. Suresh Kuarm、P. Narsimha Reddy、Peter A. Crooks、B. Rajitha

  DOI：10.1016/j.bmcl.2011.05.055

  日期：2011.7

  2-g]chromenes (7a–c), were synthesized and evaluated for their antitubercular activities against Mycobacterium tuberculosis H37RV, and cytotoxicity (CC50) in the VERO cell MABA assay. The results indicate that the furanochromene series of compounds (3a–g and 4a–d) showed only weak to moderate antitubercular activity. However, the pyranochromene analog 7b showed good antitubercular activity (IC90: 5.9 μg/mL) and

  2-苯甲酰基-3-甲基-5-氧代-5 H-呋喃[3,2- g ]色烯-6-甲醛的一系列新的巴比妥酸酯和硫代巴比妥酸酯类似物（分别为3a – g和4a – d）和6合成了-甲基-4,8-​​二氧杂-4-3,8-二氢吡喃[3,2- g ]色酮（7a – c），并评估了其对结核分枝杆菌H37RV的抗结核活性以及在VERO中的细胞毒性（CC 50）细胞MABA测定。结果表明，呋喃并二烯系列化合物（3a - g和4a - d）仅显示弱至中度​​的抗结核活性。然而，吡喃并二氢吡啶类似物7b显示出良好的抗结核活性（IC 90：5.9μg/ mL）和细胞毒性（CC 50：14.27μg/ mL）。7b的抗结核活性优于抗结核药物吡嗪酰胺（PZA； IC 90：> 20μg/ mL）。类似物7b被认为是后续结构优化的先导化合物。
• Dependence of Fluorescence Properties of Compounds from Psoralen, Angelicin, and Carbazole Series on the Character of Their Terminal Substituents
  作者：V. S. Sibirtsev、A. Yu. Tolmachev、V. V. Suslov、A. V. Garabadzhiu、V. F. Traven'

  DOI：10.1023/b:rujo.0000003169.96393.1d

  日期：2003.6

  Absorption, luminescence excitation and emission spectra of nine compounds from 4,8,4'-tri-methylpsoralen, 4,4'-dimethylangelicin, and 1,2,3,4-tetrahydrocarbazole series with various terminal substituents were studied in water and 2-propanol. Proceeding from the data obtained in the present and also some previous studies we have formulated the main rules concerning a general mechanism of changes in the fluorescence characteristics of DNA-specific dyes depending on their chemical structure, substrate properties, and measurement medium.