4,4'-(4-(thiophen-2-yl)pyridine-2,6-diyl)diphenol | 1383781-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-(4-(thiophen-2-yl)pyridine-2,6-diyl)diphenol
• 英文别名: 4-[6-(4-Hydroxyphenyl)-4-thiophen-2-ylpyridin-2-yl]phenol；4-[6-(4-hydroxyphenyl)-4-thiophen-2-ylpyridin-2-yl]phenol
• CAS: 1383781-97-2
• 化学式: C₂₁H₁₅NO₂S
• 分子量: 345.422
• InChiKey: CLEPAIKBAOQXMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯乙酮 在 ammonium acetate 、 碘 、 溶剂黄146 作用下， 反应 3.0h， 生成 4,4'-(4-(thiophen-2-yl)pyridine-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

文献信息

• Acidic ionic liquid immobilized on cellulose: an efficient and recyclable heterogeneous catalyst for the solvent-free synthesis of hydroxylated trisubstituted pyridines
  作者：Shailesh P. Satasia、Piyush N. Kalaria、Dipak K. Raval

  DOI：10.1039/c3ra23052j

  日期：——

  The synthesis of a novel cellulose supported acidic ionic liquid (Cell-IL) for the solvent-free synthesis of hydroxylated trisubstituted pyridines is reported. Cell-IL was prepared by immobilization of an acidic ionic liquid [1-butyl-3-(3-trimethoxypropyl)-1H-imidazol-3-ium hydrogen sulfate] on cellulose. The viability of this concept has been confirmed by FT-IR, TGA-DTG, 1H NMR and elemental analysis. The Cell-IL showed good thermal stability and exhibited a high catalytic activity in the synthesis of a series of hydroxylated trisubstituted pyridines. It was recovered and reused for the model reaction three times without an appreciable change in its activity.

  报道了一种新型纤维素支持的酸性离子液体（Cell-IL）的合成，用于无溶剂合成羟基化三取代吡啶。Cell-IL是通过将一种酸性离子液体（[1-丁基-3-(3-三甲氧基丙基)-1H-咪唑-3-ium氢硫酸盐]）固定在纤维素上制备的。通过FT-IR、TGA-DTG、1H NMR和元素分析确认了该概念的可行性。Cell-IL显示出良好的热稳定性，并在一系列羟基化三取代吡啶的合成中表现出高催化活性。它被回收并在模型反应中重复使用三次，其活性没有显著变化。
• Solvent- and catalyst-free synthesis of new hydroxylated trisubstituted pyridines under microwave irradiation
  作者：Guodong Yin、Qiong Liu、Junrui Ma、Nengfang She

  DOI：10.1039/c2gc35243e

  日期：——

  A facile solvent- and catalyst-free method for the synthesis of a series of new hydroxylated 2,4,6-trisubstituted pyridines under microwave irradiation was developed. The expected products were obtained through a simplified purification process without protection of the hydroxyl group. UV-Vis and fluorescence spectra of these conjugated multi-hydroxyl compounds were also investigated.

  开发了一种简便的无溶剂和无催化剂的方法，用于在微波辐射下合成一系列新的羟基化的2,4,6-三取代的吡啶。通过简化的纯化过程无需保护羟基即可获得预期的产物。还研究了这些共轭多羟基化合物的UV-Vis和荧光光谱。
• 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.