Click chemistry: studies on the synthesis of novel fluorous tagged triazol-4-yl substituted quinazoline derivatives and their biological evaluation--theoretical and experimental validation

European Journal of Medicinal Chemistry
P Mani ChandrikaA Raghu Ram Rao

Abstract

The formation of N- and O-propargylated quinazoline derivatives 2, 3 from quinazol-4-ones 1 was theoretically predicted by optimizations at B3LYP/6-31G* level, analysed kinetically and thermodynamically. Theoretical predictions are validated by experiment to observe the trends and found deviation. Thus, compound 1 was propargylated in basic media to obtain compound 2 and 3 in definite proportions. Each compound was further subjected to [3+2] cycloaddition using perfluoroalkyl azides through Click reaction under Sharpless conditions, and obtained a series of novel perfluoroalkyl-1H,1,2,3-triazol-4-yl substituted quinazolines 4, 5, and 6. All the compounds were screened for antimicrobial activity and identified potential compounds.

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Jan 6, 2005·Journal of the American Chemical Society·Fahmi HimoValery V Fokin

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Citations

Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Abdelaaziz OuahrouchLahcen El Ammari
Mar 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdelaaziz OuahrouchHassan B Lazrek
Aug 1, 2014·Future Medicinal Chemistry·Eva PrchalováMartin Kotora
Jan 31, 2019·Archiv der Pharmazie·Iwona E GłowackaDorota G Piotrowska

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