2-Chloroacetylamino-pyrrolo[1,2-a]azepine-3-ethyl ester 3 was synthesized, condensed with ammonium thiocyanate to obtain a hybrid molecule of pyrrolo [1,2-a]azepine and thiazolidinone moiety 4. Coupling of the obtained hybrid molecule with the appropriate aldehydes or diazonium salt afforded novel substituted hybrids 5a,b and 6. Chemical structures were confirmed by spectral and elemental analysis. The synthesized compounds were tested on liver Hep3B, lung A549, breast MCF7 cancer cell lines and normal fibroblast cells as well, using sulforhodamine-B assay method. Compound 5a showed to be potent and selective to lung A549 cancer cell line (IC50 = 13 nM/mL, S.I. = 2.9). The most potent one against MCF7 was compound 4 with IC50 value equals 12 nM/mL and S.I. = 1.4. Compounds 5b, 6 exhibited high potency and selectivity towards Hep3B cancer cells with IC50 and S.I. equal 15 nM/mL, 10.8 and 9 nM/mL, 285, respectively. The ability of the synthesized compounds 3-6 to act as modulators for cyclin dependent kinases was explored through molecular docking studies.