| 38767-63-4

• 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
• CAS: 38767-63-4
• 化学式: C₂₁H₁₇BrO₃
• 分子量: 397.268
• InChiKey: DXZRQCHOTDRBCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  、 溶剂黄146 在 一水合肼 作用下， 反应 3.0h， 以71%的产率得到1-acetyl-5-(3-bromo-4,5-dimethoxyphenyl)-3-(naphth-2-yl)-4,5-dihydro-(1H)-pyrazole
  参考文献：
  名称：

  Halogenated naphthochalcones and structurally related naphthopyrazolines with antitumor activity

  摘要：

  Three 3-(3-halo-4,5-dimethoxypheny1)-1-(2-naphthyl)prop-2-en-1 -ones 1 and three structurally related 2-pyrazolines 2 were prepared and assessed in vitro for anticancer activity. The chalcones 1 were antiproliferative with low double-digit micromolar IC50 values against six tumor cell lines whereas the pyrazolines 2 showed low single-digit micromolar IC50) values against this panel. The pyrazolines inhibited ATP binding cassette efflux transporters of types P-gp and BCRP while the chalcones inhibited selectively BCRP. All test compounds induced an accumulation of HT-29 colon carcinoma cells in the G2/M phase of the cell cycle and they interfered with the microtubule and F-actin dynamics, but only the chalcones induced apoptosis in 518A2 melanoma cells after 24 h. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.076
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Halogenated naphthochalcones and structurally related naphthopyrazolines with antitumor activity

  摘要：

  Three 3-(3-halo-4,5-dimethoxypheny1)-1-(2-naphthyl)prop-2-en-1 -ones 1 and three structurally related 2-pyrazolines 2 were prepared and assessed in vitro for anticancer activity. The chalcones 1 were antiproliferative with low double-digit micromolar IC50 values against six tumor cell lines whereas the pyrazolines 2 showed low single-digit micromolar IC50) values against this panel. The pyrazolines inhibited ATP binding cassette efflux transporters of types P-gp and BCRP while the chalcones inhibited selectively BCRP. All test compounds induced an accumulation of HT-29 colon carcinoma cells in the G2/M phase of the cell cycle and they interfered with the microtubule and F-actin dynamics, but only the chalcones induced apoptosis in 518A2 melanoma cells after 24 h. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.076

文献信息

• Halogenated naphthochalcones and structurally related naphthopyrazolines with antitumor activity
  作者：Florian Schmitt、Heidrun Draut、Bernhard Biersack、Rainer Schobert

  DOI：10.1016/j.bmcl.2016.09.076

  日期：2016.11

  Three 3-(3-halo-4,5-dimethoxypheny1)-1-(2-naphthyl)prop-2-en-1 -ones 1 and three structurally related 2-pyrazolines 2 were prepared and assessed in vitro for anticancer activity. The chalcones 1 were antiproliferative with low double-digit micromolar IC50 values against six tumor cell lines whereas the pyrazolines 2 showed low single-digit micromolar IC50) values against this panel. The pyrazolines inhibited ATP binding cassette efflux transporters of types P-gp and BCRP while the chalcones inhibited selectively BCRP. All test compounds induced an accumulation of HT-29 colon carcinoma cells in the G2/M phase of the cell cycle and they interfered with the microtubule and F-actin dynamics, but only the chalcones induced apoptosis in 518A2 melanoma cells after 24 h. (C) 2016 Elsevier Ltd. All rights reserved.