Due to importance of iminocoumarine and farmacological properties of 1,2,3-triazole development of novel derivatives from their backbones is important for development of novel compounds with potential antitumor activity. This work presents the synthesis of C-5 alkynyl benzaldehyde (3 ,4) derivatives and C-5 alkynyl salicylaldehyde (5-7) derivatives by Pd-catalysed Sonogashira cross-coupling reaction, triazole derivative of salicylaldehyde (23-27) as well as iminocoumarin derivatives 28-37. Cu-catalyzed click reactions under microvawe irradiation of 5-azidomethylsalicylicaldehyde 21 with corresponding alkynes, 1,2,3-triazole salicylaldehyde derivatives 23-27 were obtained, which are then converted to 1,2,3-triazole iminocoumarin derivatives 28-30 by reaction with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile in absolute ethanol and piperidine. Condensation reaction of salicylaldehyde and 2-(1H-benzo[d]imidazol-2-yl)acetonitrile in absolute ethanol and piperidine, iminocumarin derivative 31 was obtained, which are then converted to 1,2,3-triazole iminocoumarin derivative 33 by in situ reaction with NaN3, terminal alkyne, Et3N and CuSO4 in a solution of tert-butanol: H2O (1 : 1). Microwave assisted click reaction of 6-azido iminocoumarin derivative (34) and corresponding terminal alkynes gave 6-(1,2,3-triazolyl) iminocoumarin derivatives 35 and 37. Structural characterization of novel compounds was conducted using 1H-NMR spectroscopy. Pharmacological effects and possible biologycal targets were predicted using in silico analysis (PASS). Antiproliferative evaluation will be preformed in vitro against human malignant tumor cells.