(E)-3[-(thiophen-3-yl)methylene]chroman-4-one | 940845-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3[-(thiophen-3-yl)methylene]chroman-4-one
• 英文别名: 3-(Thiophen-3-ylmethylidene)chromen-4-one；3-(thiophen-3-ylmethylidene)chromen-4-one
• CAS: 940845-44-3
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: ZHAXJIAGKBRDOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3[-(thiophen-3-yl)methylene]chroman-4-one 、 1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以51.9%的产率得到
  参考文献：
  名称：

  2,4-Diaryl-5H-chromeno [4,3-b]pyridines: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity

  摘要：

  DOI：

  10.5012/bkcs.2012.33.9.3103
• 作为产物：
  描述：

  3-噻吩甲醛 、 2,3-二氢苯并吡喃-4-酮 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 以14%的产率得到(E)-3[-(thiophen-3-yl)methylene]chroman-4-one
  参考文献：
  名称：

  ( E )-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors

  摘要：

  A series of (E)-3-heteroarylidenechroman-4-ones (1a-r) was designed, synthesized and investigated in vitro for their ability to inhibit the enzymatic activity of both human monoamine oxidase (hMAO) isoforms, hMAO-A and hMAO-B. All the compounds were found to be selective hMAO-B inhibitors showing IC50 values in the nanomolar or micromolar range. (E)-5,7-Dichloro-3-{[(2-(dimethylamino) pyrimidin-5-yl]methylene}chroman-4-one (1c) was the most interesting compound identified in this study, endowed with higher hMAO-B potency (IC50 = 10.58 nM) and selectivity (SI > 9452) with respect to the reference selective inhibitor selegiline (IC50 = 19.60 nM, IC50 > 3431). Molecular modelling studies were performed for rationalizing at molecular level the target selective inhibition of our compounds, revealing a remarkable contribution of hydrogen bond network and water solvent. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.081

文献信息

• Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship
  作者：Uttam Thapa、Pritam Thapa、Radha Karki、Minho Yun、Jae Hun Choi、Yurngdong Jahng、Eunyoung Lee、Kyung-Hwa Jeon、Younghwa Na、Eun-Mi Ha、Won-Jea Cho、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2011.04.029

  日期：2011.8

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 2,4-Diaryl-5H-chromeno [4,3-b]pyridines: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity
  作者：Pritam Thapa、Eung-Seok Lee

  DOI：10.5012/bkcs.2012.33.9.3103

  日期：2012.9.20
• ( E )-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors
  作者：Nicoletta Desideri、Luca Proietti Monaco、Rossella Fioravanti、Mariangela Biava、Matilde Yáñez、Stefano Alcaro、Francesco Ortuso

  DOI：10.1016/j.ejmech.2016.03.081

  日期：2016.7

  A series of (E)-3-heteroarylidenechroman-4-ones (1a-r) was designed, synthesized and investigated in vitro for their ability to inhibit the enzymatic activity of both human monoamine oxidase (hMAO) isoforms, hMAO-A and hMAO-B. All the compounds were found to be selective hMAO-B inhibitors showing IC50 values in the nanomolar or micromolar range. (E)-5,7-Dichloro-3-[(2-(dimethylamino) pyrimidin-5-yl]methylene}chroman-4-one (1c) was the most interesting compound identified in this study, endowed with higher hMAO-B potency (IC50 = 10.58 nM) and selectivity (SI > 9452) with respect to the reference selective inhibitor selegiline (IC50 = 19.60 nM, IC50 > 3431). Molecular modelling studies were performed for rationalizing at molecular level the target selective inhibition of our compounds, revealing a remarkable contribution of hydrogen bond network and water solvent. (C) 2016 Elsevier Masson SAS. All rights reserved.