Open AccessCrystal engineering construction of caffeic acid derivatives with potential applications in pharmaceuticals and degradable polymeric materials
Author(s) -
Zhihan Wang,
Quinton Flores,
Hongye Guo,
Raquel Trevizo,
Xiaochan Zhang,
Shihan Wang
Publication year - 2020
Publication title -
crystengcomm
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.813
H-Index - 132
ISSN - 1466-8033
DOI - 10.1039/d0ce01403f
Subject(s) - caffeic acid , crystal engineering , crystal (programming language) , chemistry , organic chemistry , materials science , nanotechnology , combinatorial chemistry , chemical engineering , crystal structure , computer science , engineering , supramolecular chemistry , antioxidant , programming language
Natural products are precious feedstock in drug discovery and sustainable materials. This work using crystal engineering strategy, visible light, and solvent-free cycloaddition successfully constructed two caffeic acid derivatives, rel -(1 R ,2 R ,3 S ,4 S )-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate and rel -(1 R ,2 R ,3 S ,4 S )-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylic acid. Because of the multiple stereocenters, it is challenging to prepare those compounds using traditional organic synthesis methods. The crystal engineering Hirshfeld surface analysis and 2D intermolecular interaction fingerprints were applied to synthetic route design. The light resources used in this work was visible LED or free, clean, and renewable sunlight. The evidence suggested that pure stereoisomer was obtained demonstrating the stereospecificity and efficiency of the topochemical cycloaddition reaction. The derivatives exhibited free radical scavenging and antioxidant biological activities, as well as the potential inhibitory activity of fatty acid binding proteins. One of the derivatives is the precursor of the natural product Shimobashiric acid C which paves the way for the total synthesis and further study of Shimobashiric acid C. In addition, the derivatives possess photodegradability at a specific wavelength, which is very attractive for "green" degradable polymeric materials.