2-(3'-amino-4'-methylphenyl)-6,7-dimethyl-4-oxo-4H-1-benzopyran-8-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3'-amino-4'-methylphenyl)-6,7-dimethyl-4-oxo-4H-1-benzopyran-8-carboxylic acid
• 英文别名: 2-(3-Amino-4-methylphenyl)-6,7-dimethyl-4-oxo-4H-chromene-8-carboxylic acid；2-(3-amino-4-methylphenyl)-6,7-dimethyl-4-oxochromene-8-carboxylic acid
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: UJCVZABZNYUPGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3'-amino-4'-methylphenyl)-6,7-dimethyl-4-oxo-4H-1-benzopyran-8-carboxylic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以9 mg的产率得到methyl 2-(3-amino-4-methylphenyl)-6,7-dimethyl-4-oxo-4H-chromene-8-carboxylate
  参考文献：
  名称：

  Cell death triggered by synthetic flavonoids in human leukemia cells is amplified by the inhibition of extracellular signal-regulated kinase signaling

  摘要：

  A new class of methyl esters of flavonoids, with different substituents on the B ring were synthesized and evaluated for their antiproliferative activity against the human leukemia cell line HL-60. The presence of either a methyl group (1f) or a chlorine atom (1o) at position 2' of the B ring played an important role in affecting antiproliferative activity. The cytotoxic effects of these compounds were accompanied by the concentration- and time-dependent appearance of DNA- and nuclear-fragmentation, increase in the percentage of sub-G(1) cells, and processing of multiple caspases and poly(ADP-ribose)polymerase cleavage. Pretreatment of cells with the specific mitogen-activated extracellular kinases (MEK) 1/2 inhibitor PD98059, together with if and 1o, resulted in an important enhancement of cell death, which might have clinical implications for the use of both compounds in combination with MEK 1/2 inhibitors as potential therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.028
• 作为产物：
  描述：

  3-cyano-4,5-dimethyl-2-hydroxyacetophenone 在 吡啶 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(3'-amino-4'-methylphenyl)-6,7-dimethyl-4-oxo-4H-1-benzopyran-8-carboxylic acid
  参考文献：
  名称：

  Cell death triggered by synthetic flavonoids in human leukemia cells is amplified by the inhibition of extracellular signal-regulated kinase signaling

  摘要：

  A new class of methyl esters of flavonoids, with different substituents on the B ring were synthesized and evaluated for their antiproliferative activity against the human leukemia cell line HL-60. The presence of either a methyl group (1f) or a chlorine atom (1o) at position 2' of the B ring played an important role in affecting antiproliferative activity. The cytotoxic effects of these compounds were accompanied by the concentration- and time-dependent appearance of DNA- and nuclear-fragmentation, increase in the percentage of sub-G(1) cells, and processing of multiple caspases and poly(ADP-ribose)polymerase cleavage. Pretreatment of cells with the specific mitogen-activated extracellular kinases (MEK) 1/2 inhibitor PD98059, together with if and 1o, resulted in an important enhancement of cell death, which might have clinical implications for the use of both compounds in combination with MEK 1/2 inhibitors as potential therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.028

文献信息

• Synthesis of flavone-8-carboxylic acid analogues as potential antitumor agents
  作者：SJ Cutler、FM El-Kabbani、C Keane、SL Fisher-Shore、FL McCabe、RK Johnson、C De Witt Blanton

  DOI：10.1016/0223-5234(93)90127-z

  日期：1993.1

  Furan o-aminonitriles may be utilized as precursors in the synthesis of flavone-8-carboxylic acids. Some results from in vivo evaluation against P388 leukemia, colon carcinoma 38, and B16 melanoma models suggest that selected examples of the acids are potentially as effective as the antitumor compound, flavone acetic acid. The flavone-8-carboxylic acids did not exhibit significant activity against an in vitro HIV screen or an in vitro antitumor screen consisting of a cell panel of 60 lines.