(E)-1-(1-hydroxynaphthalen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one | 125574-12-1

• 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)-1-(1-hydroxynaphthalen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(1-Hydroxynaphthalen-2-YL)-3-(4-methoxyphenyl)prop-2-EN-1-one
• CAS: 125574-12-1
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: FCQCOOZSDMTDDH-MDWZMJQESA-N

物化性质

• 沸点：
  530.5±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(1-hydroxynaphthalen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以59%的产率得到3-hydroxy-2-(4-methoxyphenyl)-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

  摘要：

  Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR. We synthesized a series of flavones, 7,8-benzoflavones and 5,6-benzoflavones with varying substituents at positions 3, 3' and 4' of the (benzo)flavone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3',4'-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.035
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 4-甲氧基苯甲醛 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以76%的产率得到(E)-1-(1-hydroxynaphthalen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones

  摘要：

  制备了15种易于组装的ESIPT活性2'-羟基查尔酮，以识别具有增加量子产率的深红色晶体态荧光物质。系统的单晶XRD分析提供了结构-性质关系的趋势。

  DOI：

  10.1039/d1tc03096e

文献信息

• Complete assignments of ¹ H and ¹³ C NMR data for 21 naphthalenyl-phenyl-pyrazoline derivatives
  作者：Doseok Hwang、Hyuk Yoon、Seunghyun Ahn、Dong-Wook Kim、Dong-Ho Bae、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3981

  日期：2013.9

  To find potent new chemotherapy drugs, we designed and synthesized a series of naphthochalcones bearing naphthalenyl‐phenyl‐pyrazoline moieties. The complete 1H and 13C NMR data for these compounds are reported here and can be used to identify further new naphthochalcones bearing the desired pyrazoline moieties. Copyright © 2013 John Wiley & Sons, Ltd.

  为了寻找有效的新化疗药物，我们设计并合成了一系列带有萘基-苯基-吡唑啉部分的萘查耳酮。此处报告了这些化合物的完整 1H 和 13C NMR 数据，可用于进一步鉴定带有所需吡唑啉部分的新萘查耳酮。版权所有 © 2013 John Wiley & Sons, Ltd.
• 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.
• 154. Some 4-styrylcoumarins
  作者：Harbhajan S. Mahal、Krishnasami Venkataraman

  DOI：10.1039/jr9330000616

  日期：——
• 404. Chalkones. Synthesis of 1-p-alkoxyarylidene-5 : 6-benzocoumaran-2-ones
  作者：A. P. Khanolkar、T. S. Wheeler

  DOI：10.1039/jr9380002118

  日期：——
• MISRA SHYAM SUNDER, J. INDIAN CHEM. SOC. <JICS-AH>, 1975, 92, NO 7, 651-652
  作者：MISRA SHYAM SUNDER

  DOI：——

  日期：——