3-苯基-1-(2'-羟基萘基)-2-丙烯-1-酮 | 40649-77-2

• 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
• 中文名称: 3-苯基-1-(2'-羟基萘基)-2-丙烯-1-酮
• 英文名称: (E)-1-(2-hydroxynaphthalen-1-yl)-3-phenylprop-2-en-1-one
• 英文别名: 2'-hydroxy-5',6'-benzochalcone
• CAS: 40649-77-2
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: PFXHOOQGFLTMQH-ZRDIBKRKSA-N

物化性质

• 熔点：
  104 °C(Solv: ethanol (64-17-5))
• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 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：

  3-苯基-1-(2'-羟基萘基)-2-丙烯-1-酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以59%的产率得到β-萘黄酮
  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：

  2,3-二氢-3-苯基-1H-萘并[2,1-B]吡喃-1-酮 以 1,4-二氧六环 、 水 为溶剂， 生成 3-苯基-1-(2'-羟基萘基)-2-丙烯-1-酮
  参考文献：
  名称：

  碱性水溶液中一些2'-羟基查耳酮环化为黄烷酮的动力学和机理

  摘要：

  对于某些2'-羟基查耳酮，在其2'-羟基经过电离的pH范围（约8-11）中，查尔酮-黄酮平衡反应的速率系数已经确定。研究的查耳酮为母体2'-羟基查耳酮（I）及其以下衍生物：4'-OMe（II），6'-OMe（III），4'-OH（IV），4'，6'-Me 2（V）和5'，6'-苯并（VI）。伪一级速率系数（ķ OBS），其为有关可逆反应，是在正向和反向速率系数的总和，拟合动力学形式ķ OBS = KF甲+ ķ ' ˚F乙+ ķ “一OH –其中k和k '分别是中性和离子化查尔酮单分子环化的速率系数（ f A和f B是在相关pH下以中性和离子化形式存在的总查尔酮的分数），其中k ”是黄烷酮涉及氢氧根离子（活性为OH –）的逆反应的二级速率系数。数据分析给出了速率系数和p K a除查耳酮（IV）以外的所有分子具有不同的动力学形式。提出了一种共轭添加消除机制来解释pH值速率分布，其中一种[查尔酮

  DOI：

  10.1039/p29820001309

文献信息

• Synthesis of Chiral 3-Substituted Indanones via an Enantioselective Reductive-Heck Reaction
  作者：Ana Minatti、Xiaolai Zheng、Stephen L. Buchwald

  DOI：10.1021/jo701741y

  日期：2007.11.1

  An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.

  已经开发了有效的分子内钯催化的不对称还原-Heck反应，其取决于所用的碱，可以合成对映体富集的3-取代的茚满酮或α-外-亚甲基茚满酮。
• Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone–Flavanone Molecular Switch Scaffold
  作者：Brian M. Muller、Theodore J. Litberg、Reid A. Yocum、Chanté A. Pniewski、Marc J. Adler

  DOI：10.1021/acs.joc.6b00986

  日期：2016.7.1

  substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch’s scope, scaffolds

  以前对邻羟基查耳酮/黄酮酮分子转换支架的研究表明，简单的取代改变了发生快速相互转化的pH范围。本文中，通过将特征性苯环改变为替代的芳族体系进行了更具影响力的结构修饰。确定在这些改变之后，支架仍然是可行的，并且可达到的中点pH值的范围显着增加。为了进一步探索开关的范围，还研究了能够发生多个开关事件的支架。
• Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
  作者：Motofumi Miura、Karin Shigematsu、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2021.153480

  日期：2021.11

  flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

  在温和条件下，从相应的羟基查耳酮与催化量的氟化铯水溶液通过氧杂-迈克尔加成容易合成总共 36 种黄烷酮，其中包括多环芳环和杂环。该方法可用于作为 SARS-CoV-2 刺突蛋白的已知强效抑制剂圣草酚的可扩展合成。
• 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.
• Joshi; Shah, Journal of the Indian Chemical Society, 1952, vol. 29, p. 225,231
  作者：Joshi、Shah

  DOI：——

  日期：——