A library of 72 derivatives of quasienantiomers cinchonidine and cinchonine was prepared. Reduction of vinyl group resulted in 10, 11-dihydrocinchonidine and 10, 11-dihydrocinchonine which were used together with cinchonidine and cinchonine as starting material for the preparation of N-quaternary derivatives (total of 58 compounds). Furthermore, monosubstituted (N-ethyl, N-phenyl and N-cyclohexyl) and disubstituted (N,N-dimethyl, N,N-diethyl and N,N-diphenyl) C9-carbamates were prepared (total of 10 compounds). Oxidation of C9-hydroxyl group yielded a ketone which was further converted to ketoxime and quaternized into N-methyl and N-benzyl derivatives. For all prepared compounds, 22 of which have not been described in the literature so far, the structure was determined by standard analytical methods. Nuclear magnetic resonance spectroscopy was applied to study the conformers of the compounds in solution. The tested derivatives showed moderate to strong antibiotic potential on a representative panel of Gram-positive and Gram-negative bacteria, and derivatives with cholinesterase inhibitory potential were identified. Selected compounds showed no toxic effect on the proliferation of HEK 293T and HeLa cell lines.