(2E)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• 英文别名: (E)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: MNQXOHXCUUCAFJ-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one 、 苯肼 以 乙醇 为溶剂， 以80%的产率得到4-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-N,N-dimethylaniline
  参考文献：
  名称：

  Design, biological evaluation and 3D QSAR studies of novel dioxin-containing triaryl pyrazoline derivatives as potential B-Raf inhibitors

  摘要：

  A series of novel dioxin-containing triaryl pyrazoline derivatives C1-C20 have been synthesized. Their B-Raf inhibitory and anti-proliferation activities were evaluated. Compound C6 displayed the most potent biological activity against B-Raf(V600E) and WM266.4 human melanoma cell line with corresponding IC50 value of 0.04 mu M and GI(50) value of 0.87 mu M, being comparable with the positive controls and more potent than our previous best compounds. Moreover, C6 was selective for B-Raf(V600E) from B-Raf(WT), C-Raf and EGFR and low toxic. The docking simulation suggested the potent bioactivity might be caused by breaking the limit of previous binding pattern. A new 3D QSAR model was built with the activity data and binding conformations to conduct visualized SAR discussion as well as to introduce new directions. Stretching the backbone to outer space or totally reversing the backbone are both potential orientations for future researches. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.012
• 作为产物：
  描述：

  6-乙酰基-1,4-苯并二氧杂环 、 对二甲氨基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以80%的产率得到(2E)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  设计，合成和生物学评估含氧查耳酮作为有效和选择性的MAO-B抑制剂。

  摘要：

  本研究记录了氧化查尔酮（O1-O26）衍生物的合成及其抑制单胺氧化酶的能力。检查的所有26种衍生物均显示出对MAO-B的有效抑制活性。化合物O23对MAO-B表现出最大的抑制活性，IC 50值为0.0021 µM，其次是化合物O10和O17（IC 50分别 为0.0030和0.0034 µM）。此外，大多数衍生物均能有效抑制MAO-A和O6，是最有效的抑制剂，IC 50值为0.029 µM，其次是O3，O4，O9和O3。O2（IC 50 分别为0.035、0.053、0.072和0.082 µM）。O23对MAO-B的选择性指数（SI）值为138.1，而O20（对于MAO-B的IC 50值为0.010 µM）具有非常高的SI> 4000。在透析实验中，O6和O23对MAO-A和MAO-B的抑制作用分别恢复到了各自的可逆参考水平，表明这两种都是可逆抑制剂。动力学研究表明，O6和O23分别以K

  DOI：

  10.1016/j.bioorg.2019.103335

文献信息

• Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors
  作者：Della Grace Thomas Parambi、Jong Min Oh、Seung Cheol Baek、Jae Pil Lee、Anna Rita Tondo、Orazio Nicolotti、Hoon Kim、Bijo Mathew

  DOI：10.1016/j.bioorg.2019.103335

  日期：2019.12

  addition, most of the derivatives potently inhibited MAO-A and O6 was the most potent inhibitor with an IC50 value of 0.029 µM, followed by O3, O4, O9, and O2 (IC50 = 0.035, 0.053, 0.072, and 0.082 µM, respectively). O23 had a high selectivity index (SI) value for MAO-B of 138.1, and O20 (IC50 value for MAO-B = 0.010 µM) had an extremely high SI of >4000. In dialysis experiments, inhibitions of MAO-A and

  本研究记录了氧化查尔酮（O1-O26）衍生物的合成及其抑制单胺氧化酶的能力。检查的所有26种衍生物均显示出对MAO-B的有效抑制活性。化合物O23对MAO-B表现出最大的抑制活性，IC 50值为0.0021 µM，其次是化合物O10和O17（IC 50分别 为0.0030和0.0034 µM）。此外，大多数衍生物均能有效抑制MAO-A和O6，是最有效的抑制剂，IC 50值为0.029 µM，其次是O3，O4，O9和O3。O2（IC 50 分别为0.035、0.053、0.072和0.082 µM）。O23对MAO-B的选择性指数（SI）值为138.1，而O20（对于MAO-B的IC 50值为0.010 µM）具有非常高的SI> 4000。在透析实验中，O6和O23对MAO-A和MAO-B的抑制作用分别恢复到了各自的可逆参考水平，表明这两种都是可逆抑制剂。动力学研究表明，O6和O23分别以K
• Design, biological evaluation and 3D QSAR studies of novel dioxin-containing triaryl pyrazoline derivatives as potential B-Raf inhibitors
  作者：Yu-Shun Yang、Bing Yang、Yan Zou、Guigen Li、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2016.05.012

  日期：2016.7

  A series of novel dioxin-containing triaryl pyrazoline derivatives C1-C20 have been synthesized. Their B-Raf inhibitory and anti-proliferation activities were evaluated. Compound C6 displayed the most potent biological activity against B-Raf(V600E) and WM266.4 human melanoma cell line with corresponding IC50 value of 0.04 mu M and GI(50) value of 0.87 mu M, being comparable with the positive controls and more potent than our previous best compounds. Moreover, C6 was selective for B-Raf(V600E) from B-Raf(WT), C-Raf and EGFR and low toxic. The docking simulation suggested the potent bioactivity might be caused by breaking the limit of previous binding pattern. A new 3D QSAR model was built with the activity data and binding conformations to conduct visualized SAR discussion as well as to introduce new directions. Stretching the backbone to outer space or totally reversing the backbone are both potential orientations for future researches. (C) 2016 Elsevier Ltd. All rights reserved.