This paper describes studies on the synthesis of N-arylaminopropylpyrrolidin-2-one derivatives as antiarrhythmic, antihypertensive and α-adrenolytic agents, and the determination of their physicochemical properties such as: lipophilicity, ionisation constants and molecule shape. Twenty-three new pyrrolidin-2-one or pyrrolidine derivatives were synthesized, and the method of asymmetric synthesis of lead structure (N-(2-hydroxy-3-(4-phenylpiperazinyl)-propyl)-pyrrolidin-2-one)) was elaborated. The newly obtained compounds were tested for their pharmacological activity both in vivo and in vitro. The results obtained led to selection of some derivatives for which pharmacological activity higher or comparable to the lead structure. The pyrrolidin-2-one or pyrrolidine derivatives contain the phenylpiperazine group. For active compounds, additional physicochemical properties such as lipophilicity and ionization constants were determined. The ionization constants were assigned by potentiometric titration and calculated using pKalc module of the Pallas system. The lipophilicity was determined by reversed-phase TLC and HPLC. The partition coefficients (log P) of the tested compounds were calculated using a SciLogP programme. The chromatographic results obtained and the log P values calculated enabled calculation of the partition coefficient including experimental data and distribution coefficient. Comparison of partition or distribution coefficient to K_i values (affinity of tested compounds to α₁, and α₂-adrenergic receptor) led to formulation of QSAR relationship in those groups. Based on crystallographic results obtained for the lead structure, conformational analysis and molecular modelling for some active compounds were undertaken. The obtained results showed that 2-substituted phenylpiperazinyl moiety is a key element defining α-AR antagonist activity of synthesized compounds.