(E)-1-(1-hydroxynaphthalen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one | 57822-43-2

• 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-(3-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(1-hydroxy-[2]naphthyl)-3t-(3-methoxy-phenyl)-propenone；1-(1-hydroxy-[2]naphthyl)-3-(3-methoxy-phenyl)-propenone；1-(1-Hydroxy-[2]naphthyl)-3t-(3-methoxy-phenyl)-propenon；1-(1-Hydroxy-[2]naphthyl)-3-(3-methoxy-phenyl)-propenon
• CAS: 57822-43-2
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: VLWVNUOUJXQVQQ-FMIVXFBMSA-N

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-(3-methoxyphenyl)prop-2-en-1-one 在 吡啶 、 sodium hydroxide 、 双氧水 作用下， 生成 3-hydroxy-2-(3-methoxy-phenyl)-benzo[h]chromen-4-one
  参考文献：
  名称：

  Wagh; Jadhav, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1959, vol. 27/5 A, p. 1

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 3-甲氧基苯甲醛 生成 (E)-1-(1-hydroxynaphthalen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  21 种萘基-苯基-吡唑啉衍生物的 1H 和 13C NMR 数据的完整归属

  摘要：

  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.

  DOI：

  10.1002/mrc.3981

文献信息

• 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.
• v. Kostanecki, Chemische Berichte, 1908, vol. 41, p. 785
  作者：v. Kostanecki

  DOI：——

  日期：——
• Torricelli, 1922, vol. 2, p. 100,101
  作者：Torricelli

  DOI：——

  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：——
• 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.