N'-(6-chloro-4,4-dimethyl-3,4-dihydroquinolin-2-yl)-N,N-dimethylethane-1,2-diamine | 1443446-66-9

• 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: N'-(6-chloro-4,4-dimethyl-3,4-dihydroquinolin-2-yl)-N,N-dimethylethane-1,2-diamine
• 英文别名: 2-[(6-chloro-4,4-dimethyl-1,3-dihydroquinolin-2-ylidene)amino]-N,N-dimethylethanamine
• CAS: 1443446-66-9
• 化学式: C₁₅H₂₂ClN₃
• 分子量: 279.813
• InChiKey: QUOHZMPLEAMKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-chlorophenyl)-3-methylbut-2-enamide 在 劳森试剂 、 aluminum (III) chloride 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.0h， 生成 N'-(6-chloro-4,4-dimethyl-3,4-dihydroquinolin-2-yl)-N,N-dimethylethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents

  摘要：

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.038

文献信息

• Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents
  作者：Eun Lee、SeulAa Han、Guo Hua Jin、Hwa Jin Lee、Woo-Young Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2013.04.038

  日期：2013.7

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.