A novel class of functionalized-calix[4]arene such as 1,4-dihydropyridine-calix[4]arene, acridinecalix[4]arene and pyrimidine-calix[4]arene were synthesized using multicomponent reaction. These compounds have been characterized by 1 H NMR, 13 C NMR and HRMS. Fluorescent and 1 H NMR titration investigations reveal that these derivatives have the high binding constant towards the monosaccharide and disaccharide in aqueous solution. The formation of complex was also supported by electrospray mass spectrometry.