2-[2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl]-ethanol | 1273018-11-3

• 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: 2-[2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl]-ethanol
• 英文别名: 2-[2,6-Dichloro-4-(2-chlorophenyl)-3-quinolyl]ethanol；2-[2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl]ethanol
• CAS: 1273018-11-3
• 化学式: C₁₇H₁₂Cl₃NO
• 分子量: 352.647
• InChiKey: FOPTYXHKRBXEBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl]-ethanol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(2-azidoethyl)-2,6-dichloro-4-(2-chlorophenyl)quinoline 、 2-azido-3-(2-azidoethyl)-6-chloro-4-(2-chlorophenyl)quinoline
  参考文献：
  名称：

  Synthesis and biological assay of 4-aryl-6-chloro-quinoline derivatives as novel non-nucleoside anti-HBV agents

  摘要：

  A series of 4-aryl-6-chloro-quinoline derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely the abilities to inhibit the secretion of HBV surface antigen (HBsAg), HBV e antigen (HBeAg), and replication of HBV DNA in HepG 2.2.15 cells. Most of the compounds exhibited moderate inhibitory activity against the secretion of HBsAg and HBeAg. Nine compounds (3, 5, 6, 7, 10, 14, 17, 20, 24) showed significant inhibition against HBV DNA replication with IC50 values in the range of 4.4-9.8 mu M, which were comparative to that of positive control tenofovir. Of them, compounds 10, 17, and 20 had low cytotoxicities, resulting in high SI values, >551.2, >143.7, and >284.5, respectively. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.006
• 作为产物：
  描述：

  2-(2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl)ethylacetate 在 ammonium acetate 、 水 作用下， 以 甲醇 为溶剂， 以84%的产率得到2-[2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl]-ethanol
  参考文献：
  名称：

  Synthesis and biological assay of 4-aryl-6-chloro-quinoline derivatives as novel non-nucleoside anti-HBV agents

  摘要：

  A series of 4-aryl-6-chloro-quinoline derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely the abilities to inhibit the secretion of HBV surface antigen (HBsAg), HBV e antigen (HBeAg), and replication of HBV DNA in HepG 2.2.15 cells. Most of the compounds exhibited moderate inhibitory activity against the secretion of HBsAg and HBeAg. Nine compounds (3, 5, 6, 7, 10, 14, 17, 20, 24) showed significant inhibition against HBV DNA replication with IC50 values in the range of 4.4-9.8 mu M, which were comparative to that of positive control tenofovir. Of them, compounds 10, 17, and 20 had low cytotoxicities, resulting in high SI values, >551.2, >143.7, and >284.5, respectively. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.006

文献信息

• Synthesis and biological assay of 4-aryl-6-chloro-quinoline derivatives as novel non-nucleoside anti-HBV agents
  作者：Rui-Hua Guo、Quan Zhang、Yun-Bao Ma、Xiao-Yan Huang、Jie Luo、Li-Jun Wang、Chang-An Geng、Xue-Mei Zhang、Jun Zhou、Zhi-Yong Jiang、Ji-Jun Chen

  DOI：10.1016/j.bmc.2011.01.006

  日期：2011.2

  A series of 4-aryl-6-chloro-quinoline derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely the abilities to inhibit the secretion of HBV surface antigen (HBsAg), HBV e antigen (HBeAg), and replication of HBV DNA in HepG 2.2.15 cells. Most of the compounds exhibited moderate inhibitory activity against the secretion of HBsAg and HBeAg. Nine compounds (3, 5, 6, 7, 10, 14, 17, 20, 24) showed significant inhibition against HBV DNA replication with IC50 values in the range of 4.4-9.8 mu M, which were comparative to that of positive control tenofovir. Of them, compounds 10, 17, and 20 had low cytotoxicities, resulting in high SI values, >551.2, >143.7, and >284.5, respectively. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.