1-(3-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one

• 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: 1-(3-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
• 英文别名: 1-(3-Hydroxyphenyl)-3-pyridin-2-ylprop-2-en-1-one；1-(3-hydroxyphenyl)-3-pyridin-2-ylprop-2-en-1-one
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: VQKPHRGDVPGCLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one 、 1-(3-hydroxy-phenacyl)-pyridinium; iodide 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 以59.3%的产率得到3,3'-([2,4'-bipyridine]-2',6'-diyl)diphenol
  参考文献：
  名称：

  Topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of dihydroxylated 2,6-diphenyl-4-aryl pyridines

  摘要：

  A new series of thirty-six dihydroxylated 2,6-diphenyl-4-aryl pyridines containing hydroxyl groups at the ortho, meta, or para position of 2- and 6-phenyl rings attached to the central pyridine were designed and synthesized. They were evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Most of the compounds with hydroxyl moiety either at the meta or para position of 2- or 6-phenyl ring in combination with thienyl or furyl group at 4-position of central pyridine displayed significant topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for the compounds 9-11, 15-17, 19, 21-23, 28, and 41. Among all the synthesized compounds, compound 17 emerged as the most promising topoisomerase II inhibitor with significant cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.002
• 作为产物：
  描述：

  吡啶-2-甲醛 、 3-羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以48.8%的产率得到1-(3-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of dihydroxylated 2,6-diphenyl-4-aryl pyridines

  摘要：

  A new series of thirty-six dihydroxylated 2,6-diphenyl-4-aryl pyridines containing hydroxyl groups at the ortho, meta, or para position of 2- and 6-phenyl rings attached to the central pyridine were designed and synthesized. They were evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Most of the compounds with hydroxyl moiety either at the meta or para position of 2- or 6-phenyl ring in combination with thienyl or furyl group at 4-position of central pyridine displayed significant topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for the compounds 9-11, 15-17, 19, 21-23, 28, and 41. Among all the synthesized compounds, compound 17 emerged as the most promising topoisomerase II inhibitor with significant cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.002

文献信息

• Topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study of dihydroxylated 2,6-diphenyl-4-aryl pyridines
  作者：Radha Karki、Chanju Song、Tara Man Kadayat、Til Bahadur Thapa Magar、Ganesh Bist、Aarajana Shrestha、Younghwa Na、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmc.2015.04.002

  日期：2015.7

  A new series of thirty-six dihydroxylated 2,6-diphenyl-4-aryl pyridines containing hydroxyl groups at the ortho, meta, or para position of 2- and 6-phenyl rings attached to the central pyridine were designed and synthesized. They were evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Most of the compounds with hydroxyl moiety either at the meta or para position of 2- or 6-phenyl ring in combination with thienyl or furyl group at 4-position of central pyridine displayed significant topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for the compounds 9-11, 15-17, 19, 21-23, 28, and 41. Among all the synthesized compounds, compound 17 emerged as the most promising topoisomerase II inhibitor with significant cytotoxicity. (C) 2015 Elsevier Ltd. All rights reserved.
• Design, synthesis and in vitro antimicrobial activity of fused pyridine-pyrimidine hybrids
  作者：Desai, Nisheeth C.、Khasiya, Ashvinkumar G.

  DOI：10.56042/ijc.v61i6.59339

  日期：——