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Green Synthesis of Fluorescent Peptidomimetic Triazoles from Biomass‐Derived 5‐(Chloromethyl)furfural
Author(s) -
Salim Kunnummal Mangott Muhammed,
Shamsiya Aranhikkal,
Damodaran Bahulayan
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802310
Subject(s) - furfural , peptidomimetic , azide , cycloaddition , alkyne , chemistry , combinatorial chemistry , click chemistry , sonogashira coupling , organic chemistry , catalysis , peptide , palladium , biochemistry
Abstract An easy and green synthetic approach to functional peptidomimetics starting from a biomass‐derived platform chemical 5‐(chloromethyl)furfural (CMF) is described. The overall protocol involves four synthetic steps in which the key step is an intermolecular [3+2] azide‐alkyne click cycloaddition between alkyne functionalized heterocyclic privileged scaffolds and CMF‐azide. The alkyne functionalized heterocyclic scaffolds were obtained from multicomponent coupling reactions (MCRs) and the azide scaffold was derived from biomass source. The peptidomimetics thus obtained showed excellent fluorescent properties with large Stoke's shift comparable to commercial fluorophores. The drug property descriptors of the peptidomimetics are also promising and are well within the limits of Lipinski's rule of five.