6-bromo-3-(4'-oxo-chroman-3'-ylidenemethyl)-chromen-4-one | 178808-77-0

• 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: 6-bromo-3-(4'-oxo-chroman-3'-ylidenemethyl)-chromen-4-one
• 英文别名: 6-Bromo-3-[(4-oxochromen-3-ylidene)methyl]chromen-4-one
• CAS: 178808-77-0
• 化学式: C₁₉H₁₁BrO₄
• 分子量: 383.198
• InChiKey: YLFANOQJLUWHKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 6-溴-3-甲酰色酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.3h， 以73%的产率得到6-bromo-3-(4'-oxo-chroman-3'-ylidenemethyl)-chromen-4-one
  参考文献：
  名称：

  Synthesis, characterization, DNA-binding studies and acetylcholinesterase inhibition activity of new 3-formyl chromone derivatives

  摘要：

  A series of new substituted 3-formyl chromone derivatives (4-6) were synthesized by one step reaction methodology by knoevenagel condensation, structurally similar to known bisintercalators. The new compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and analytical data. The in vitro DNA binding profile of compounds (4-6) was carried out by absorption, fluorescence and viscosity measurements. It was found that synthesized compounds, especially compound 6 (evident from binding constant value) bind strongly with calf thymus DNA, presumably via an intercalation mode. Additionally, molecular docking studies of compounds (4-6) were carried out with B-DNA (PDBID: 1BNA) which revealed that partial intercalative mode of mechanism is operational in synthesized compounds (4-6) with CT-DNA. The binding constants evaluated from fluorescence spectroscopy of compounds with CT-DNA follows the order compound 6> compound 5 > compound 4. All the compounds (4-6) were screened for acetylcholinesterase inhibition assay. It can be inferred from data, that compound (6) showed potent AChE inhibition having IC50 = 0.27 mu M, almost in vicinity to reference drug Tacrine (IC50 = 0.19 mu M). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2013.11.019

文献信息

• Synthesis, characterization, DNA-binding studies and acetylcholinesterase inhibition activity of new 3-formyl chromone derivatives
  作者：Mehtab Parveen、Ali Mohammed Malla、Zahid Yaseen、Akhtar Ali、Mahboob Alam

  DOI：10.1016/j.jphotobiol.2013.11.019

  日期：2014.1

  A series of new substituted 3-formyl chromone derivatives (4-6) were synthesized by one step reaction methodology by knoevenagel condensation, structurally similar to known bisintercalators. The new compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and analytical data. The in vitro DNA binding profile of compounds (4-6) was carried out by absorption, fluorescence and viscosity measurements. It was found that synthesized compounds, especially compound 6 (evident from binding constant value) bind strongly with calf thymus DNA, presumably via an intercalation mode. Additionally, molecular docking studies of compounds (4-6) were carried out with B-DNA (PDBID: 1BNA) which revealed that partial intercalative mode of mechanism is operational in synthesized compounds (4-6) with CT-DNA. The binding constants evaluated from fluorescence spectroscopy of compounds with CT-DNA follows the order compound 6> compound 5 > compound 4. All the compounds (4-6) were screened for acetylcholinesterase inhibition assay. It can be inferred from data, that compound (6) showed potent AChE inhibition having IC50 = 0.27 mu M, almost in vicinity to reference drug Tacrine (IC50 = 0.19 mu M). (C) 2013 Elsevier B.V. All rights reserved.