(E)-3-(4-(dimethylamino)phenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one | 39875-70-2

• 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)-3-(4-(dimethylamino)phenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-dimethylaminophenyl)-1-(1-hydroxynaphthalin-2-yl)prop-2-en-1-one；3-(4-dimethylamino-phenyl)-1-(1-hydroxy-[2]naphthyl)-propenone；3-(4-Dimethylamino-phenyl)-1-(1-hydroxy-[2]naphthyl)-propenon；(2E)-3-[4-(dimethylamino)phenyl]-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one；(E)-3-[4-(dimethylamino)phenyl]-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• CAS: 39875-70-2
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: VXPHVHMTDLBAKR-NTEUORMPSA-N

物化性质

• 沸点：
  543.3±50.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(dimethylamino)phenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以72%的产率得到2-(4-(dimethylamino)phenyl)-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  Chemical Modification of the Multitarget Neuroprotective Compound Fisetin

  摘要：

  Many factors are implicated in age-related central nervous system (CNS) disorders, making it unlikely that modulating only a single factor will provide effective treatment. Perhaps a better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Recently, we identified an orally active, neuroprotective, and cognition-enhancing molecule, the flavonoid fisetin, that is effective in several animal models of CNS disorders. Fisetin has direct antioxidant activity and can also increase the intracellular levels of glutathione (GSH), the major endogenous antioxidant. In addition, fisetin has both neurotrophic and anti-inflammatory activity. However, its relatively high EC50 in cell based assays, low lipophilicity, high topological polar surface area (tPSA), and poor bioavailability suggest that there is room for medicinal chemical improvement. Here we describe a multitiered approach to screening that has allowed us to identify fisetin derivatives with significantly enhanced activity in an in vitro neuroprotection model while at the same time maintaining other key activities.

  DOI：

  10.1021/jm2012563
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 对二甲氨基苯甲醛 在 四乙酰基二硼氧烷 、 乙酸酐 、 溶剂黄146 作用下， 生成 (E)-3-(4-(dimethylamino)phenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  通过由可烯醇的1，3-二酮制得的简单的花菁

  摘要：

  1.在硼焦乙酸酯存在下，通过2-乙酰基萘酚-（1）和2-乙酰基-3-氧基硫代萘基与醛的缩合反应获得深色的硼配合物。

  DOI：

  10.1002/hlca.19510340218

文献信息

• Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones
  作者：Alix Tordo、Erwann Jeanneau、Mathieu Bordy、Yann Bretonnière、Jens Hasserodt

  DOI：10.1039/d1tc03096e

  日期：——

  Fifteen easily assembled ESIPT-active 2′-hydroxychalcones were prepared to identify deep-red crystal-state fluorophores with increased quantum yields. Systematic single-crystal XRD analysis furnished trends in the structure–property relationship.

  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。
• 一类含查尔酮结构的新型荧光母核的合成
  申请人：南京大学

  公开号：CN111039807A

  公开（公告）日：2020-04-21

  一类含查尔酮结构的荧光母核，它具有如下通式。本发明公开了一类新型的含查尔酮结构的荧光母核的合成方法及其在荧光探针设计中的应用。
• Torricelli, 1922, vol. 2, p. 100,103
  作者：Torricelli

  DOI：——

  日期：——
• Rajendar Reddy, Kamreddy; Mogilaiah, Kaleru; Sreenivasulu, Bathula, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 3, p. 643 - 645
  作者：Rajendar Reddy, Kamreddy、Mogilaiah, Kaleru、Sreenivasulu, Bathula

  DOI：——

  日期：——
• HOSNI G.; SAAD S. F., ACTA CHIM. ACAD. SCI. HUNG. <ACAS-A2>, 1975, 86, NO 3, 263-267
  作者：HOSNI G.、 SAAD S. F.

  DOI：——

  日期：——