Abstract:
:Novel derivatives of 4-oxo-3-methylcytisine with phenyl moiety bonded to starting molecule through various spacers were obtained from the 9-amino, -halo, -formyl and 11-halo precursors by reductive alkylation of amines, generation of amide, as well as thio- and carboxamide functions, cross-coupling reactions, aldehyde condensation and reduction of unsaturated 'C-C' bonds. Ability of synthesized compounds to influence the learning and memory was preliminary assessed in conditioned passive avoidance reflex (CPAR) test in rats. It was shown, that derivatives with phenyl group at 11 carbon atom influence the learning and memory in CPAR test more effectively than other compounds. The hit-compound (3-methyl-11-(2-phenylvinyl)-3,5,6-trihydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocine-4,8(1H)-dione) with the best values of 'latency' and 'time spent in the dark compartment' has been identified as a perspective scaffold for synthesis of novel derivatives of (-)-cytisine with potential neuropharmacological activity.
journal_name
Nat Prod Resjournal_title
Natural product researchauthors
Tsypysheva I,Petrova P,Koval'skaya A,Lobov A,Sapozhnikova T,Makara N,Gabdrakhmanova S,Zarudii Fdoi
10.1080/14786419.2019.1622106subject
Has Abstractpub_date
2021-01-01 00:00:00pages
207-215issue
2eissn
1478-6419issn
1478-6427journal_volume
35pub_type
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