(E)-3-(4-chlorophenyl)-1-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one | 38280-24-9

• 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: (E)-3-(4-chlorophenyl)-1-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one
• CAS: 38280-24-9
• 化学式: C₁₉H₁₃ClO₂
• 分子量: 308.764
• InChiKey: AHTYQZALRBUBBT-YRNVUSSQSA-N

物化性质

• 熔点：
  82 °C(Solv: ethanol (64-17-5))
• 沸点：
  517.6±50.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-3-吡啶甲醛 、 (E)-3-(4-chlorophenyl)-1-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one 以82%的产率得到
  参考文献：
  名称：

  REDDY K. R.; MOGILAIAH K.; SREENIVASULU B., J. INDIAN CHEM. SOC., 63,(1986) N 11, 984-985

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 、 4-氯苯甲醛 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以68%的产率得到(E)-3-(4-chlorophenyl)-1-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein

  摘要：

  Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 20 and 40 on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.074

文献信息

• REDDY K. R.; MOGILAIAH K.; SREENIVASULU B., J. INDIAN CHEM. SOC., 63,(1986) N 11, 984-985
  作者：REDDY K. R.、 MOGILAIAH K.、 SREENIVASULU B.

  DOI：——

  日期：——
• Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein
  作者：Kapil Juvale、Veronika F.S. Pape、Michael Wiese

  DOI：10.1016/j.bmc.2011.10.074

  日期：2012.1

  Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 20 and 40 on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition. (C) 2011 Elsevier Ltd. All rights reserved.