New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their Click Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion

Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. Cu-I catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption-emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated.

Automated summary

In this study, novel fluorescent coumarins modified with an azido-group on the side chain were synthesized and their photophysical properties and crystal structure characteristics were investigated. The possibilities of fluorescent labeling were demonstrated by testing the synthesized coumarins with a closo-dodecaborate derivative bearing a terminal alkynyl group. Fluorescent conjugates were formed through Cu-I catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The antiproliferative activity and uptake of the compounds against various human cell lines were evaluated.