(E)-1-(4-hydroxyphenyl)-3-(1-(3,4,5-trimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (E)-1-(4-hydroxyphenyl)-3-(1-(3,4,5-trimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-hydroxyphenyl)-3-[1-(3,4,5-trimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-yl]prop-2-en-1-one
• 化学式: C₂₉H₂₄N₂O₅
• 分子量: 480.52
• InChiKey: YYBRIYAAKKIMSE-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 戴斯-马丁氧化剂 、 barium(II) hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (E)-1-(4-hydroxyphenyl)-3-(1-(3,4,5-trimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  DNA-binding affinity and anticancer activity of β-carboline–chalcone conjugates as potential DNA intercalators: Molecular modelling and synthesis

  摘要：

  A new series of DNA-interactive beta-carboline-chalcone conjugates have been synthesized and evaluated for their in vitro cytotoxicity and DNA-binding affinity. It has been observed that most of these new hybrids have shown potent cytotoxic activities on A-549 ( lung adenocarcinoma) cell lines with IC50 values lower than 10 mu M. The hybrid 7b is more effective against some of the selected cancer cell lines with IC50 values less than 50 mu M. In addition, compounds 7e, 7k, 7p-u has displayed significant elevation in Delta T-m of DNA in comparison to Adriamycin, suggesting significant interaction and remarkable DNA stabilization. The DNA intercalation of these new hybrids has been investigated by fluorescence titration, DNA viscosity measurements, molecular docking as well as molecular dynamics and the results are in agreement with the thermal denaturation studies. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.007

文献信息

• DNA-binding affinity and anticancer activity of β-carboline–chalcone conjugates as potential DNA intercalators: Molecular modelling and synthesis
  作者：Nagula Shankaraiah、K.P. Siraj、Shalini Nekkanti、Vunnam Srinivasulu、Pankaj Sharma、Kishna Ram Senwar、Manda Sathish、M.V.P.S. Vishnuvardhan、Sistla Ramakrishna、Chetna Jadala、Narayana Nagesh、Ahmed Kamal

  DOI：10.1016/j.bioorg.2015.02.007

  日期：2015.4

  A new series of DNA-interactive beta-carboline-chalcone conjugates have been synthesized and evaluated for their in vitro cytotoxicity and DNA-binding affinity. It has been observed that most of these new hybrids have shown potent cytotoxic activities on A-549 ( lung adenocarcinoma) cell lines with IC50 values lower than 10 mu M. The hybrid 7b is more effective against some of the selected cancer cell lines with IC50 values less than 50 mu M. In addition, compounds 7e, 7k, 7p-u has displayed significant elevation in Delta T-m of DNA in comparison to Adriamycin, suggesting significant interaction and remarkable DNA stabilization. The DNA intercalation of these new hybrids has been investigated by fluorescence titration, DNA viscosity measurements, molecular docking as well as molecular dynamics and the results are in agreement with the thermal denaturation studies. (C) 2015 Elsevier Inc. All rights reserved.