(6-Acetyl-2-cyano-3,4-dimethylphenyl) 4-methyl-3-nitrobenzoate | 1400815-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (6-Acetyl-2-cyano-3,4-dimethylphenyl) 4-methyl-3-nitrobenzoate
• 英文别名: (6-acetyl-2-cyano-3,4-dimethylphenyl) 4-methyl-3-nitrobenzoate
• CAS: 1400815-83-9
• 化学式: C₁₉H₁₆N₂O₅
• 分子量: 352.346
• InChiKey: ILNMEVZDRPXOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6-Acetyl-2-cyano-3,4-dimethylphenyl) 4-methyl-3-nitrobenzoate 在 吡啶 、 potassium hydroxide 作用下， 生成 6,7-dimethyl-2-(4'-methyl-3'-nitrophenyl)-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
• 作为产物：
  描述：

  3-cyano-4,5-dimethyl-2-hydroxyacetophenone 、 4-甲基-3-硝基苯甲酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 (6-Acetyl-2-cyano-3,4-dimethylphenyl) 4-methyl-3-nitrobenzoate
  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

• Cell death triggered by synthetic flavonoids in human leukemia cells is amplified by the inhibition of extracellular signal-regulated kinase signaling
  作者：Sara Rubio、Francisco León、José Quintana、Stephen Cutler、Francisco Estévez

  DOI：10.1016/j.ejmech.2012.07.028

  日期：2012.9

  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.