In this work, two novel hybrid compounds 4a and 4b, consisting of a β-carboline ring which is connected to a quinoline derivative via the chloroquine model by an amide bond in positions 3 and 6, were synthesized and characterized. In order to achieve this goal, building blocks for these compounds were prepared, a quinoline derivative (7-chloroquinolin-4-yl) glycine and 3- and 6-substituted β-carboline amines 1e and 2e. The preparation of amines 1e and 2e at the β-carboline ring positions starts from the methyl ester of tryptophan and 5-methoxytryptamine and takes place in five reaction steps. First, Pictet-Spengler condensation produces tetrahydro-β-carbolines (1a and 2a), which are then oxidized to the corresponding β-carbolines 1b and 2b. In case of amine from series 1, the methyl ester at position 3 is reduced to the primary alcohol 1c. This is followed by the conversion of the alcohol 1c to the corresponding azide 1d by using ADMP under basic conditions, and reduction to the primary amine 1e. The ether moiety at the position 6 of the compound 2b is hydrolized in acidic conditions to corresponding phenol 2c, which in the reaction of nucleophilic substitution under basic conditions is converted to compound 2d in which the terminal amino group carries a Boc-protecting group. The amino group is then deprotected by acid hydrolysis of the carbamate, and amine 2e is formed. The final products 4a and 4b were obtained by the reaction of amines 1e and 2e with (7-chloroquinolin-4-yl) glycine (3), by using standard coupling conditions (T3P, TEA, DMF). Structures of the newly prepared compounds were confirmed using conventional analytical and spectroscopic methods (1H i 13C NMR, MS, IR). All four novel derivatives meet all of the Lipinski's and Veber's criteria for good oral bioavailability of potential drugs. SwissADME tool predicts good oral bioavailability of all four derivatives. Further studies will investigate biological activity of the prepared coumpounds.