6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one | 1444006-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one
• 英文别名: 6-Bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2-one；6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2-one
• CAS: 1444006-14-7
• 化学式: C₁₄H₁₄BrNO₄
• 分子量: 340.173
• InChiKey: MZOAVDRFYQEBMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one 、 3-氟苯基硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以74%的产率得到6-(3-fluorophenyl)-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 1,6-diaryl pyridin-2(1H)-one analogs

  摘要：

  A series of 1,6-diaryl pyridin-2(1H)-one analogs were designed and synthesized via consecutive Chan-Lam coupling and Suzuki coupling. These novel compounds were evaluated for their antiproliferative activity against two tumor cell lines (SKOV-3 and HepG2). Compounds 1b, 1c, 1e and 1f displayed comparable in vitro cytotoxicity with taxol, while their in vivo antitumor activity was less effective than taxol. In addition, cell cycle assay indicated that these 1,6-diaryl pyridin-2(1H)-one compounds induced cell cycle arrest in the G1/M phase in the HepG2 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.008
• 作为产物：
  描述：

  3,4,5-三甲氧基苯硼酸 、 2-溴-6-羟基吡啶 在 吡啶 、 吡啶-N-氧化物 、 copper diacetate 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 1,6-diaryl pyridin-2(1H)-one analogs

  摘要：

  A series of 1,6-diaryl pyridin-2(1H)-one analogs were designed and synthesized via consecutive Chan-Lam coupling and Suzuki coupling. These novel compounds were evaluated for their antiproliferative activity against two tumor cell lines (SKOV-3 and HepG2). Compounds 1b, 1c, 1e and 1f displayed comparable in vitro cytotoxicity with taxol, while their in vivo antitumor activity was less effective than taxol. In addition, cell cycle assay indicated that these 1,6-diaryl pyridin-2(1H)-one compounds induced cell cycle arrest in the G1/M phase in the HepG2 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.008

文献信息

• Synthesis and biological evaluation of novel 1,6-diaryl pyridin-2(1H)-one analogs
  作者：Taijie Chen、Yu Luo、Youhong Hu、Bo Yang、Wei Lu

  DOI：10.1016/j.ejmech.2013.04.008

  日期：2013.6

  A series of 1,6-diaryl pyridin-2(1H)-one analogs were designed and synthesized via consecutive Chan-Lam coupling and Suzuki coupling. These novel compounds were evaluated for their antiproliferative activity against two tumor cell lines (SKOV-3 and HepG2). Compounds 1b, 1c, 1e and 1f displayed comparable in vitro cytotoxicity with taxol, while their in vivo antitumor activity was less effective than taxol. In addition, cell cycle assay indicated that these 1,6-diaryl pyridin-2(1H)-one compounds induced cell cycle arrest in the G1/M phase in the HepG2 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.