6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)quinolin-2(1H)-one | 1046154-83-9

• 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: 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)quinolin-2(1H)-one
• 英文别名: 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)-1H-quinolin-2-one
• CAS: 1046154-83-9
• 化学式: C₁₇H₁₃Cl₂NO₂
• 分子量: 334.202
• InChiKey: DUJKCRPTAPXLNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)quinolin-2(1H)-one 在 吡啶 、 苯膦酰二氯 作用下， 反应 2.0h， 生成 2-(2,6-dichloro-4-(2-chlorophenyl)quinolin-3-yl)ethylacetate
  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：

  γ-丁内酯 、 2-氨基-2',5-二氯二苯酮 在 lithium hexamethyldisilazane 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 26.76h， 以86%的产率得到6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  作为新型非核苷类抗乙肝病毒药物的6-氯-4-（2-氯苯基）-3-（2-羟乙基）喹啉-2（1 H）-一衍生物的构效关系研究

  摘要：

  合成了一系列新型的6-氯-4-（2-氯苯基）-3-（2-羟乙基）喹啉-2（1 H）-一衍生物，并评估了其抗乙型肝炎病毒（anti-HBV）的活性。体外研究其结构-活性关系（SAR）。大多数合成的化合物都具有有效的抗HBV活性，其中有希望的化合物44对肝炎表面抗原（HBsAg）（IC 50  = 0.010 mM，SI> 135），戊型肝炎抗原（HBeAg）的分泌具有显着的抑制作用。（IC 50  = 0.026 mM，SI> 51）和HBV DNA复制（IC 50  = 0.045 mM）。初步机理研究表明化合物44 可以主要增强HBV ENI（enhancer I），EN-II（enhancer II）的转录活性。

  DOI：

  10.1016/j.ejmech.2010.11.019

文献信息

• Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives
  作者：Pi Cheng、Quan Zhang、Yun-Bao Ma、Zhi-Yong Jiang、Xue-Mei Zhang、Feng-Xue Zhang、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2008.05.065

  日期：2008.7

  A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively). (c) 2008 Elsevier Ltd. All rights reserved.
• 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.
• Structure–activity relationships study of 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one derivatives as novel non-nucleoside anti-hepatitis B virus agents
  作者：Rui-Hua Guo、Quan Zhang、Yun-Bao Ma、Jie Luo、Chang-An Geng、Li-Jun Wang、Xue-Mei Zhang、Jun Zhou、Zhi-Yong Jiang、Ji-Jun Chen

  DOI：10.1016/j.ejmech.2010.11.019

  日期：2011.1

  A series of novel 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one derivatives were synthesized and evaluated for anti-hepatitis B virus (anti-HBV) activities in vitro to explore their structure–activity relationships (SARs). Most of the synthesized compounds possessed potent anti-HBV activity, of which the promising compound 44 exhibited significantly inhibitory potency against the

  合成了一系列新型的6-氯-4-（2-氯苯基）-3-（2-羟乙基）喹啉-2（1 H）-一衍生物，并评估了其抗乙型肝炎病毒（anti-HBV）的活性。体外研究其结构-活性关系（SAR）。大多数合成的化合物都具有有效的抗HBV活性，其中有希望的化合物44对肝炎表面抗原（HBsAg）（IC 50  = 0.010 mM，SI> 135），戊型肝炎抗原（HBeAg）的分泌具有显着的抑制作用。（IC 50  = 0.026 mM，SI> 51）和HBV DNA复制（IC 50  = 0.045 mM）。初步机理研究表明化合物44 可以主要增强HBV ENI（enhancer I），EN-II（enhancer II）的转录活性。