2-(4-oxo-2,3-diphenyl-4H-chromen-8-yl)acetic acid | 87627-20-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2-(4-oxo-2,3-diphenyl-4H-chromen-8-yl)acetic acid
• 英文别名: (4-Oxo-2,3-diphenyl-4H-1-benzopyran-8-yl)acetic acid；2-(4-oxo-2,3-diphenylchromen-8-yl)acetic acid
• CAS: 87627-20-1
• 化学式: C₂₃H₁₆O₄
• 分子量: 356.378
• InChiKey: BWJOQFQALICWAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  220-224 °C(Solv: acetic acid (64-19-7))
• 沸点：
  583.5±50.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-oxo-2,3-diphenyl-4H-chromen-8-yl)acetonitrile 在 硫酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以86%的产率得到2-(4-oxo-2,3-diphenyl-4H-chromen-8-yl)acetic acid
  参考文献：
  名称：

  Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives

  摘要：

  This paper describes the synthesis and the antiproliferative activities of compounds 9a-r, 3-aryl analogs of flavone-8-acetic acid that bear diverse substituents on the benzene rings at the 2- and 3-positions of the flavone nucleus. Their direct and indirect cytotoxicities were evaluated against HT-29 human colon adenocarcinoma cell lines, A549 lung adenocarcinoma cell lines and Human Peripheral Blood Mononuclear Cells (HPBMCs). The results indicate that most of the compounds bearing electron-withdrawing substituents (9b-m) exhibited moderate direct cytotoxicities. And compounds 9e and 9i showed comparable indirect cytotoxicities with 5, 6-dimethylxanthenone-4-acetic acid (DMXAA), and low direct cytotoxicities toward HPBMCs. Interestingly, the compounds 9n-r bearing methoxy groups at the 2- or 3-position of the flavone nucleus exhibited higher indirect cytotoxicities against A549 cell lines than DMXAA, and lower cytotoxicities against HPBMCs. In addition, compounds 9p-r were found to be able to induce tumor necrosis factor alpha (TNF-alpha) production in HPBMCs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.030

文献信息

• Atassi; Briet; Berthelon, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 393 - 402
  作者：Atassi、Briet、Berthelon、Collonges

  DOI：——

  日期：——
• ATASSI, G.;BRIET, PH.;BERTHELON, J. -J.;COLLONGES, F., EUR. J. MED. CHEM., 1985, 20, N 5, 393-402
  作者：ATASSI, G.、BRIET, PH.、BERTHELON, J. -J.、COLLONGES, F.

  DOI：——

  日期：——
• Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives
  作者：Guang-Hua Yan、Xiao-Fang Li、Bing-Chen Ge、Xiu-Dong Shi、Yu-Fang Chen、Xue-Mei Yang、Jiang-Ping Xu、Shu-Wen Liu、Pei-Liang Zhao、Zhong-Zhen Zhou、Chun-Qiong Zhou、Wen-Hua Chen

  DOI：10.1016/j.ejmech.2014.11.030

  日期：2015.1

  This paper describes the synthesis and the antiproliferative activities of compounds 9a-r, 3-aryl analogs of flavone-8-acetic acid that bear diverse substituents on the benzene rings at the 2- and 3-positions of the flavone nucleus. Their direct and indirect cytotoxicities were evaluated against HT-29 human colon adenocarcinoma cell lines, A549 lung adenocarcinoma cell lines and Human Peripheral Blood Mononuclear Cells (HPBMCs). The results indicate that most of the compounds bearing electron-withdrawing substituents (9b-m) exhibited moderate direct cytotoxicities. And compounds 9e and 9i showed comparable indirect cytotoxicities with 5, 6-dimethylxanthenone-4-acetic acid (DMXAA), and low direct cytotoxicities toward HPBMCs. Interestingly, the compounds 9n-r bearing methoxy groups at the 2- or 3-position of the flavone nucleus exhibited higher indirect cytotoxicities against A549 cell lines than DMXAA, and lower cytotoxicities against HPBMCs. In addition, compounds 9p-r were found to be able to induce tumor necrosis factor alpha (TNF-alpha) production in HPBMCs. (C) 2014 Elsevier Masson SAS. All rights reserved.