Design, synthesis and fluorescence property evaluation of blue emitting triazole-linked chromene peptidomimetics

Design, synthesis and fluorescence property evaluation of blue emitting triazole-linked chromene... for the three-step synthesis of two types of blue emitting chromene peptidomimetics is described. The peptidomimet- ics were synthesized via a copper-catalyzed [3+2] azide- alkyne cycloaddition between chromene alkynes obtained from a three-component reaction and the peptide azides obtained from Ugi or Mannich type multicomponent reac- tions. The photophysical properties of the peptidomimetics are comparable with commercial fluorophores. Computa- tional studies using drug property descriptors support the possibility of using these molecules for modulating difficult target classes having large, flat, and groove-shaped binding sites. 451nm 341nm Keywords MCRs · Triazole · Ugi reaction · Mannich reaction · Click chemistry · Chromene · Beyond rule of 5 (bRo5) Introduction Electronic supplementary material The online version of this article (doi:10.1007/s11030-017-9744-9) contains supplementary Chromenes or benzopyrans are potential privileged oxy- material, which is available to authorized users. gen heterocycles that have been known for their wide B D. Bahulayan variety of therapeutic properties [1,2] such as anti-tumour [3], anti-cancer [3], anti-oxidant [5], anti-malarial [6], anti- inflammatory [7], anti-microbial [8], anti-viral [9], anti- Department of Chemistry, University of Calicut, Malappuram, Kerala 673635, India fungal [10], anti-proliferative [11], anti-HIV [12] and acetyl- 123 586 Mol Divers (2017) 21:585–596 Fig. 1 a Structure of Molecular Diversity Springer Journals

Design, synthesis and fluorescence property evaluation of blue emitting triazole-linked chromene peptidomimetics

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Springer International Publishing
Copyright © 2017 by Springer International Publishing Switzerland
Life Sciences; Biochemistry, general; Organic Chemistry; Polymer Sciences; Pharmacy
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