3,3'-(4-tert-butylbenzylidene)bis(4-hydroxycoumarin)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3'-(4-tert-butylbenzylidene)bis(4-hydroxycoumarin)
• 英文别名: 3,3'-((4-(tert-butyl)phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)；3,3'-(4-Tertbutylbenzylidene)-bis-(4-hydroxycoumarin)；3-[(4-tert-butylphenyl)-(4-hydroxy-2-oxochromen-3-yl)methyl]-4-hydroxychromen-2-one
• 化学式: C₂₉H₂₄O₆
• 分子量: 468.506
• InChiKey: FMNRYDJHEQDBIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 对叔丁基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3,3'-(4-tert-butylbenzylidene)bis(4-hydroxycoumarin)
  参考文献：
  名称：

  Synthesis of biscoumarin and dihydropyran derivatives as two novel classes of potential anti-bacterial derivatives

  摘要：

  一系列双香豆素（1–4）和二氢吡喃（5–8）衍生物作为新的抗菌剂成功合成。通过单晶X射线衍射研究确认了三种代表性化合物1、5和7的分子结构。在针对金黄色葡萄球菌（S. aureus ATCC 29213）、耐甲氧西林金黄色葡萄球菌（MRSA XJ 75302）、万古霉素中介金黄色葡萄球菌（Mu50 ATCC 700699）和美国300（洛杉矶县克隆，LAC）进行测试的化合物中，化合物1和2表现出了最强的抗菌活性。此外，通过密度泛函理论（DFT）[B3LYP/6-31G*]方法计算了双香豆素1–4中的氢键能。

  DOI：

  10.1007/s12272-015-0614-7

文献信息

• Fast highly efficient 'on-solvent' non catalytic cascade transformation of benzaldehydes and 4-hydroxycoumarin into bis(4-hydroxycoumarinyl)arylmethanes
  作者：Michail Elinson、Anatoly N. Vereshchagin、Olga O. Sokolova

  DOI：10.24820/ark.5550190.p010.023

  日期：——

  Non-catalytic cascade reaction of benzaldehydes and two equivalents of 4-hydroxycoumarin initiated by reflux in propanol results in the fast (15 min) and efficient formation of substituted tetrahydro-1H-xanthen-1-ones in 93–98% yields. The developed fast cascade approach to the substituted bis(4hydroxycoumarinyl)arylmethanes, which are known as medicinally relevant substances with anti-HIV, antibiotic

  苯甲醛和两当量 4-羟基香豆素在丙醇中回流引发的非催化级联反应导致取代四氢-1H-xanthen-1-ones 的快速（15 分钟）和有效形成，产率为 93-98%。取代双（4羟基香豆素基）芳基甲烷被称为具有抗HIV、抗生素、抗炎和抗癌活性的药用物质，从面向多样性的大规模过程的角度来看，开发的快速级联方法是有益的并且代表了用于级联反应策略的快速、高效和环境友好的合成概念。
• Synthesis of biscoumarin and dihydropyran derivatives with promising antitumor and antibacterial activities
  作者：Jing Li、Yun-Peng Sui、Jia-Jia Xin、Xin-Liang Du、Jiang-Tao Li、Hai-Ru Huo、Hai Ma、Wei-Hao Wang、Hai-Yu Zhou、Hong-Dan Zhan、Zhu-Ju Wang、Chun Li、Feng Sui、Xia Li

  DOI：10.1016/j.bmcl.2015.10.063

  日期：2015.12

  Two series of biscoumarin (1-3) and dihydropyran (4-12) derivatives were successfully synthesized as new antitumor and antibacterial agents. The molecular structures of four representative compounds 2, 4, 7 and 10 were confirmed by single crystal X-ray diffraction study. The synthesized compounds (1-12) were evaluated for their antitumor activities against human intestinal epithelial adenocarcinoma cell line (HuTu80), mammary adenocarcinoma cell line (4T1) and pancreatic cancer cell line (PANC1) and antibacterial activities against one drug-sensitive Staphylococcus aureus (S. aureus ATCC 29213) strain and three MRSA strains (MRSA XJ 75302, Mu50, USA 300 LAC). The further mechanism study demonstrated that the most potent compound 1 could obviously inhibit the proliferation of cancer cells via the mechanism to induce apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.
• 10.3998/ark.5550190.p010.023
  作者：Elinson, Michail N.、Vereshchagin, Anatoly N.、Sokolova, Olga O.

  DOI：10.3998/ark.5550190.p010.023

  日期：——