(E)-2-[4-(pyrrolidin-1-yl)benzylidene]-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-2-[4-(pyrrolidin-1-yl)benzylidene]-2,3-dihydro-1H-inden-1-one
• 英文别名: (2E)-2-[(4-pyrrolidin-1-ylphenyl)methylidene]-3H-inden-1-one
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: XJKDJUQOHYKBES-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1-吡咯啉基)苯甲醛 、 1-茚酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以94%的产率得到(E)-2-[4-(pyrrolidin-1-yl)benzylidene]-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  卤代芳基和杂环标记的2,3-二氢-1 H-茚满-1候选物的超快合成，抗菌和抗真菌研究

  摘要：

  我们描述了卤代芳基和杂环标记的2，3-二氢-1 H-茚满一酮衍生物的成功合成，以及它们的抗菌和抗真菌特性。通过研磨，搅拌和超声辐照方法合成了来自2，3-二氢-1 H-茚基-1-一的总共15种衍生物。这些发现表明，超声技术在时间和合成性能方面越来越令人满意。测试了合成的化合物对两种革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和两种革兰氏阴性菌（大肠杆菌和寻常变形杆菌）以及两种真菌剂的抗菌活性。黑曲霉和白色念珠菌）。发现大多数化合物都具有强大的抗菌作用，并具有广谱抗菌活性。同样，几乎没有化合物显示出对黑曲霉和白色念珠菌具有有效的抗真菌特性。通过FT-IR，1 H NMR，13 C NMR和HRMS光谱技术对合成的化合物进行表征。 图形摘要

  DOI：

  10.1007/s00706-021-02772-0

文献信息

• Biological Activity and Molecular Docking Studies of Curcumin-Related α,β-Unsaturated Carbonyl-Based Synthetic Compounds as Anticancer Agents and Mushroom Tyrosinase Inhibitors
  作者：Syed Nasir Abbas Bukhari、Ibrahim Jantan、Oya Unsal Tan、Muhammad Sher、M. Naeem-ul-Hassan、Hua-Li Qin

  DOI：10.1021/jf501145b

  日期：2014.6.18

  Hyperpigmentation in human skin and enzymatic browning in fruits, which are caused by tyrosinase enzyme, are not desirable. Investigations in the discovery of tyrosinase enzyme inhibitors and search for improved cytotoxic agents continue to be an important line in drug discovery and development. In present work, a new series of 30 compounds bearing α,β-unsaturated carbonyl moiety was designed and synthesized following curcumin as model. All compounds were evaluated for their effects on human cancer cell lines and mushroom tyrosinase enzyme. Moreover, the structure-activity relationships of these compounds are also explained. Molecular modeling studies of these new compounds were carried out to explore interactions with tyrosinase enzyme. Synthetic curcumin-like compounds (2a-b) were identified as potent anticancer agents with 81-82% cytotoxicity. Five of these newly synthesized compounds (1a, 8a-b, 10a-b) emerged to be the potent inhibitors of mushroom tyrosinase, providing further insight into designing compounds useful in fields of food, health, and agriculture.
• US4921827A
  申请人：——

  公开号：US4921827A

  公开（公告）日：1990-05-01