(E)-N-chrysen-6-yl-4-(4-methylpiperazin-1-yl)-4-oxobut-2-enamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (E)-N-chrysen-6-yl-4-(4-methylpiperazin-1-yl)-4-oxobut-2-enamide
• 化学式: C₂₇H₂₅N₃O₂
• 分子量: 423.514
• InChiKey: OTWYNBCIVVJNCA-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-硝基联苯 在 三氢化钐 、 TEA 、 碘 、 氯甲酸异丁酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-N-chrysen-6-yl-4-(4-methylpiperazin-1-yl)-4-oxobut-2-enamide
  参考文献：
  名称：

  Polycyclic aromatic compounds as anticancer agents: structure–activity relationships of chrysene and pyrene derivatives

  摘要：

  A large number of diamides and diamines were synthesized using 6-amino chrysene and 1-amino pyrene as starting materials. A structure-activity study with cis-platinum as internal control against animal and human tumor lines was carried out in vitro. This study indicated that the in vitro cytotoxicity toward these lines depends on the functionality present in the molecules. The diamino compounds were found to be more potent than the diamides, and these were equally active irrespective of the end heterocyclic group, whereas the activity of the diamides was strongly dependent on the terminal unit. In general, the diamides containing chrysene as the chromophore were more active than those with a pyrene ring. The size of the end heterocyclic ring, along with the nature of the spacer connecting the polycyclic ring to the heterocyclic ring, seemed to affect the biological activity in certain cell lines. Hemolysis experiments on a lead compound established that it had activities similar to those described for membrane-stabilizing agents. This agent also demonstrated the capacity to produce differentiation in leukemia cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00297-2

文献信息

• Polycyclic aromatic compounds as anticancer agents: structure–activity relationships of chrysene and pyrene derivatives
  作者：Bimal K Banik、Frederick F Becker

  DOI：10.1016/s0968-0896(00)00297-2

  日期：2001.3

  A large number of diamides and diamines were synthesized using 6-amino chrysene and 1-amino pyrene as starting materials. A structure-activity study with cis-platinum as internal control against animal and human tumor lines was carried out in vitro. This study indicated that the in vitro cytotoxicity toward these lines depends on the functionality present in the molecules. The diamino compounds were found to be more potent than the diamides, and these were equally active irrespective of the end heterocyclic group, whereas the activity of the diamides was strongly dependent on the terminal unit. In general, the diamides containing chrysene as the chromophore were more active than those with a pyrene ring. The size of the end heterocyclic ring, along with the nature of the spacer connecting the polycyclic ring to the heterocyclic ring, seemed to affect the biological activity in certain cell lines. Hemolysis experiments on a lead compound established that it had activities similar to those described for membrane-stabilizing agents. This agent also demonstrated the capacity to produce differentiation in leukemia cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.