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The trifluoroacylation reaction of pyrrolodiazacycloalkanones under sealed vessel conditions has been studied. The introduction of a trifluoroacetyl substituent at the secondary amino group into the structure of bi- and tricyclic pyrrolodiazacycloalkanones led to a significant increase in bioavailability, in particular an increase in the lipophilicity coefficient up to 36.17%. Tricyclic benzopyrroloimidazolones were revealed as the most stable ligands at the binding site of the enzyme cyclin-dependent kinase 2. [ABSTRACT FROM AUTHOR]