(1E,4Z,6E)-1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,4Z,6E)-1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
• 英文别名: (1E,4Z,6E)-1-(4-((t-butyldimethylsilyl)oxy)-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
• 化学式: C₂₇H₃₄O₆Si
• 分子量: 482.649
• InChiKey: VJVIFHBSLBEDDT-ZZLFSMTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1E,4Z,6E)-1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one 、 3'-(2-(t-butoxy)-2-oxoethoxy)-3-oxo-3H-spiro [isobenzofuran-1,9'-xanthen]-6'-yl propiolate 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到3'-(2-(t-butoxy)-2-oxoethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl (E)-3-(4-((1E,3Z,6E)-7-(4-((tbutyldimethylsilyl)oxy)-3-methoxyphenyl)-3-hydroxy-5-oxohepta-1,3,6-trien-1-yl)-2-methoxyphenoxy)acrylate
  参考文献：
  名称：

  Exploiting fluorescein based drug conjugates for fluorescent monitoring in drug delivery

  摘要：

  Anticancer drugs connected to fluorescein based chemosensors by different biodegradable linkers were investigated for fluorescent monitoring in drug delivery models. The drug release triggered by chemo- and bio-hydrolytic environments was visualized on the basis of "switch on" fluorescence of the fluorophore moiety of fluorescein-drug conjugates. The conjugation of free phenolic hydroxyl of fluorescein chemosensor to the hydroxyl group of the drugs was employed by biodegradable oxy- and amino acrylate linkers. The chemosensor also possesses a free carboxylic group for potential conjugation to a specific carrier for targeted drug delivery applications. Fluorescent monitoring of drug release, quantum yield and other spectroscopic characteristics of our novel fluorescein-drug conjugates were measured and discussed. The work offers a versatile fluorophore platform for the fluorescent observation of drug delivery. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.11.057
• 作为产物：
  描述：

  姜黄素 、 叔丁基二甲基氯硅烷 在 咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以40%的产率得到(1E,4Z,6E)-1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Exploiting fluorescein based drug conjugates for fluorescent monitoring in drug delivery

  摘要：

  Anticancer drugs connected to fluorescein based chemosensors by different biodegradable linkers were investigated for fluorescent monitoring in drug delivery models. The drug release triggered by chemo- and bio-hydrolytic environments was visualized on the basis of "switch on" fluorescence of the fluorophore moiety of fluorescein-drug conjugates. The conjugation of free phenolic hydroxyl of fluorescein chemosensor to the hydroxyl group of the drugs was employed by biodegradable oxy- and amino acrylate linkers. The chemosensor also possesses a free carboxylic group for potential conjugation to a specific carrier for targeted drug delivery applications. Fluorescent monitoring of drug release, quantum yield and other spectroscopic characteristics of our novel fluorescein-drug conjugates were measured and discussed. The work offers a versatile fluorophore platform for the fluorescent observation of drug delivery. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.11.057

文献信息

• Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives
  作者：La-or Somsakeesit、Thanaset Senawong、Pakit Kumboonma、Somprasong Saenglee、Arunta Samankul、Gulsiri Senawong、Chavi Yenjai、Chanokbhorn Phaosiri

  DOI：10.1016/j.bmcl.2020.127171

  日期：2020.6

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.
• Exploiting fluorescein based drug conjugates for fluorescent monitoring in drug delivery
  作者：Andrii Bazylevich、Leonid D. Patsenker、Gary Gellerman

  DOI：10.1016/j.dyepig.2016.11.057

  日期：2017.4

  Anticancer drugs connected to fluorescein based chemosensors by different biodegradable linkers were investigated for fluorescent monitoring in drug delivery models. The drug release triggered by chemo- and bio-hydrolytic environments was visualized on the basis of "switch on" fluorescence of the fluorophore moiety of fluorescein-drug conjugates. The conjugation of free phenolic hydroxyl of fluorescein chemosensor to the hydroxyl group of the drugs was employed by biodegradable oxy- and amino acrylate linkers. The chemosensor also possesses a free carboxylic group for potential conjugation to a specific carrier for targeted drug delivery applications. Fluorescent monitoring of drug release, quantum yield and other spectroscopic characteristics of our novel fluorescein-drug conjugates were measured and discussed. The work offers a versatile fluorophore platform for the fluorescent observation of drug delivery. (C) 2016 Elsevier Ltd. All rights reserved.