methyl 2-[2-(acridin-9-ylimino)-3-(4-bromophenyl)-4-oxo-1,3-thiazolan-5-yliden]acetate | 1414600-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 2-[2-(acridin-9-ylimino)-3-(4-bromophenyl)-4-oxo-1,3-thiazolan-5-yliden]acetate
• 英文别名: methyl 2-[2-acridin-9-ylimino-3-(4-bromophenyl)-4-oxo-1,3-thiazolidin-5-ylidene]acetate
• CAS: 1414600-06-8
• 化学式: C₂₅H₁₆BrN₃O₃S
• 分子量: 518.39
• InChiKey: WVAFLQDWQHLBQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  97.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 1-acridin-9-yl-3-(4-bromophenyl)thiourea 以 甲醇 为溶剂， 以79%的产率得到methyl 2-[2-(acridin-9-ylimino)-3-(4-bromophenyl)-4-oxo-1,3-thiazolan-5-yliden]acetate
  参考文献：
  名称：

  DNA binding acridine–thiazolidinone agents affecting intracellular glutathione

  摘要：

  Three new acridine-thiazolidinone derivatives (2a-2c) have been synthesized and their interactions with calf thymus DNA and a number of cell lines (leukemic cells HL-60 and L1210 and human epithelial ovarian cancer cell lines A2780) were studied. The compounds 2a-2c possessed high affinity to calf thymus DNA and their binding constants determined by spectrofluorimetry were in the range of 1.37 x 10(6)-5.89 x 10(6) M (1). All of the tested derivatives displayed strong cytotoxic activity in vitro, the highest activity in cytotoxic tests was found for 2c with IC50 = 1.3 +/- 0.2 mu M (HL-60), 3.1 +/- 0.4 mu M (L1210), and 7.7 +/- 0.5 mu M (A2780) after 72 h incubation. The cancer cells accumulated acridine derivatives very fast and the changes of the glutathione level were confirmed. The compounds inhibited proliferation of the cells and induced an arrest of the cell cycle and cell death. Their influence upon cells was associated with their reactivity towards thiols and DNA binding activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.068