3-hydroxy-2-(2-phenylethenyl)benzopyran-4-one

• 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: 3-hydroxy-2-(2-phenylethenyl)benzopyran-4-one
• 英文别名: E-3-hydroxy-2-styryl chromone；3-hydroxy-2-styrylchromone；trans-3-hydroxy-2-(β-phenylvinyl)-4H-1-benzopyran-4-one；3-hydroxy-2-[(E)-2-phenylethenyl]chromen-4-one
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: FVCHDTCZUBXONT-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-hydroxy-2-(2-phenylethenyl)benzopyran-4-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88.63%的产率得到(E)-3-bromo-2-(2-phenylvinyl)-4H-chromen-4-one
  参考文献：
  名称：

  Stereoselective Bromination of 2-Vinyl Chromones Using NBS

  摘要：

  A simple one-step synthetic methodology for stereoselective synthesis of E- and Z-3-bromo-2-vinyl chromones in quantitative yield in polar solvents under ambient conditions without the use of catalysts is reported.

  DOI：

  10.1080/00397910903534007
• 作为产物：
  描述：

  2'-Hydroxy-2-cinnamylideneacetophenone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3-hydroxy-2-(2-phenylethenyl)benzopyran-4-one
  参考文献：
  名称：

  Synthesis of ten membered di-oxa-carbocyclic annulated flavones and olefin tethered bisflavone derivatives–olefin ring closing / cross metathesis

  摘要：

  DOI：

  10.24820/ark.5550190.p011.644

文献信息

• Epoxidation studies of 2-styrylchromones using jacobsen's catalyst and hydrogen peroxide and iodosylbenzene as oxidants
  作者：Clementina M. M. Santos、Artur M. S. Silva、José A. S. Cavaleiro、Tamás Patonay、Albert Lévai

  DOI：10.1002/jhet.5570430526

  日期：2006.9

  The epoxidation of 2-styrylchromones 2a-h using Jacobsen's Mn(III)[salen] complex 1 as catalyst is reported for the first time. Several studies were performed using both hydrogen peroxide and iodosylbenzene as oxidants, in order to obtain the α,β-epoxy-2-styrylchromones 3a-h regioselectively. Due to the low reactivity of the substrates and the highly unstable character of the formed epoxides, reactions

  首次报道了使用雅各布森的Mn（III）[salen]配合物1作为催化剂的2-苯乙烯基色酮2a-h的环氧化。使用过氧化氢和碘基苯作为氧化剂进行了数项研究，以选择性地获得α，β-环氧-2-苯乙烯基色酮3a-h。由于底物的低反应性和所形成的环氧化物的高度不稳定的特性，应在较低的转化率下中断反应以获得可接受的收率，尤其是在使用过氧化氢的情况下。
• Synthesis and docking studies on styryl chromones exhibiting cytotoxicity in human breast cancer cell line
  作者：Seema Bhatnagar、Shakti Sahi、Puneet Kackar、Swati Kaushik、Manan K. Dave、Akshara Shukla、Ashita Goel

  DOI：10.1016/j.bmcl.2010.05.108

  日期：2010.8

  The search for small molecules that preferentially target the functionally important surfaces of estrogen receptor and disrupt the transcriptional activity in the cell has emerged as a promising area towards rationale based drug design. Herein, we report substituted styryl chromones as a new class of compounds that exhibit selectivity for ER beta binding at the second binding site of HT and antiproliferative activity in human breast cancer cell line. (c) 2010 Elsevier Ltd. All rights reserved.
• (E)-2-Styrylchromones as potential anti-norovirus agents
  作者：Joana Rocha-Pereira、Ricardo Cunha、Diana C.G.A. Pinto、Artur M.S. Silva、Maria São José Nascimento

  DOI：10.1016/j.bmc.2010.05.006

  日期：2010.6.15

  Human noroviruses (NoV) are now recognized as the most frequent cause of outbreaks and sporadic cases of acute gastroenteritis. Despite the significant economic impact and considerable morbidity of norovirus disease, no drug or vaccine is currently available to treat or prevent this disease, therefore the discovery of anti-norovirus drugs is urgent.In the present work, a total of 12 structure related chromone and (E)-2-styrylchromones were evaluated for their potential anti-norovirus activity using the murine norovirus (MNV) as a surrogate model for human NoV.From the 12 compounds studied, six (E)-2-styrylchromones were found to have with interesting antinorovirus activity. The best compounds of the series were (E)-5-hydroxy-2-styrylchromone and (E)-4'-methoxy-2-styrylchromone with an IC50 approximate to 7 mu M. A first insight into the mechanism of action of these compounds was possible. An interesting relationship between the anti-norovirus activity and the chemical structure was observed. The present study points out that the (E)-2-styrylchromones skeleton is an important one which deserves to be developed and further explored as new antiviral drugs against NoV. (C) 2010 Elsevier Ltd. All rights reserved.
• DHOUBHADEL, S. P.;TULADHAR, SUDERSAN, M.;TULADHAR, SARBAJNA, M.;WAGLEY, P+, INDIAN J. CHEM., 1981, 20, N 6, 511-512
  作者：DHOUBHADEL, S. P.、TULADHAR, SUDERSAN, M.、TULADHAR, SARBAJNA, M.、WAGLEY, P+

  DOI：——

  日期：——
• US5552551A
  申请人：——

  公开号：US5552551A

  公开（公告）日：1996-09-03