2-[3-(3,4-dimethoxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide | 1172616-37-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[3-(3,4-dimethoxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)prop-2-en-1-one
• CAS: 1172616-37-3
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: QPXCESUENPDHKS-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 乙酰甲喹 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以68%的产率得到2-[3-(3,4-dimethoxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide
  参考文献：
  名称：

  2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: A novel cluster of tumor-specific cytotoxins which reverse multidrug resistance

  摘要：

  A series of 2-(3-aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides 3a-1 were prepared by condensation of various aryl aldehydes with 2-acetyl-3-methylquinoxaline-1,4-dioxide 2. These compounds inhibit the growth of human Molt 4/C8 and CEM T-lymphocytes and the IC50 values are mainly in the 5-30 mu M range. The quinoxaline 1,4-dioxide 3j inhibited the growth of 58 human tumor cell lines, particularly leukemic and breast cancer neoplasms. All of the compounds 3a-1 reversed the multidrug resistance (MDR) properties of murine L-5178Y leukemic cells which were transfected with the human MDR1 gene. The MDR-reversing effect may be due to the conjugated p-electron system forming a weak electron charge transfer complex with the P-glycoprotein-mediated efflux pump. The compounds in series 2 and 3 were assessed against HL-60, HSC-2, HSC-3 and HSC-4 malignant cells as well as HGF, HPC and HPLF normal cell lines which revealed that the majority of the compounds displayed a greater toxicity to neoplastic than normal cells. Various ways in which the project may be expanded are presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.021

文献信息

• 2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: A novel cluster of tumor-specific cytotoxins which reverse multidrug resistance
  作者：Umashankar Das、Hari N. Pati、Atulya K. Panda、Erik De Clercq、Jan Balzarini、Joseph Molnár、Zoltán Baráth、Imre Ocsovszki、Masami Kawase、Li Zhou、Hiroshi Sakagami、Jonathan R. Dimmock

  DOI：10.1016/j.bmc.2009.04.021

  日期：2009.6

  A series of 2-(3-aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides 3a-1 were prepared by condensation of various aryl aldehydes with 2-acetyl-3-methylquinoxaline-1,4-dioxide 2. These compounds inhibit the growth of human Molt 4/C8 and CEM T-lymphocytes and the IC50 values are mainly in the 5-30 mu M range. The quinoxaline 1,4-dioxide 3j inhibited the growth of 58 human tumor cell lines, particularly leukemic and breast cancer neoplasms. All of the compounds 3a-1 reversed the multidrug resistance (MDR) properties of murine L-5178Y leukemic cells which were transfected with the human MDR1 gene. The MDR-reversing effect may be due to the conjugated p-electron system forming a weak electron charge transfer complex with the P-glycoprotein-mediated efflux pump. The compounds in series 2 and 3 were assessed against HL-60, HSC-2, HSC-3 and HSC-4 malignant cells as well as HGF, HPC and HPLF normal cell lines which revealed that the majority of the compounds displayed a greater toxicity to neoplastic than normal cells. Various ways in which the project may be expanded are presented. (C) 2009 Elsevier Ltd. All rights reserved.