Synthesis of acridine, bisacridine and quinoline derivatives with 1,2-azolic, pyridine and ferrocene fragments. Vestsi Natsyyanal’nai akademii navuk Belarusi
https://doi.org/10.29235/1561-8331-2020-56-4-445-456
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Abstract
Natural and synthetic derivatives of acridine and pyrimidoquinoline series are of considerable interest for study as antiviral, antitumor, antibacterial, antiparasitic agents; they are also useful in the treatment of Alzheimer’s disease. The combination of acridine and pyrimidoquinoline cycles with other pharmacophore groups can lead to a synergistic effect of their properties, the appearance of new types of biological activity, as well as a reducing of the severity of side effects. The synthesis of new derivatives of 8,9,10,12-tetrahydrobenzo[a]acridin-11(7H)-one and 10,12-dihydrobenzo[f] pyrimido [4,5-b] quinoline-9,11 (7H, 8H)-dione containing isoxazole, isothiazole heterocycles, ferrocene fragment, as well as nicotinic and isonicotinic acid residues covalently attached via ester groups to different positions of the aromatic nucleus, is described. A three-component cascade condensation of aromatic amines, aldehydes and cyclic β —dicarbonyl compounds was carried out by refluxing in butanol. The heat effects of the cyclization reaction have been determined using the DFT / B3LYP1 / MIDI method. The cytotoxic activity of the synthesized compounds was assessed on four different cancer cell lines (RKO, COLO320, LS174T, SW480).
Keywords
benzoacridines,
pyrimidoquinolines, 1,2-azoles,
pyridines,
ferrocenes,
2-naphthylamine,
1,3-cyclohexane-dione,
5,5-dimethylcyclohexanedione,
2,4,6-trihydroxypyrimidine,
esters,
cascade three-component condensation,
quantum chemical modeling
Supporting agencies: This work has been performed with a partial financial support of Russian Foundation for Fundamental Research, grant 20-58-00005-Бел_а, and Belarusian Republican Foundation for Fundamental Research, grant Х20Р-017. All biotesting works were performed at the Jilin Medical Institute of the People’s Republic of China. The authors express their gratitude to Professor Wenliang Li of the Jilin Medical University of China for providing the biotesting data
About the Authors
E. A. Akishina
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Russian Federation
Russian Federation
Ekaterina A. Akishina - Postgraduate student, Junior Researcher.
13, Surganov Str., 220072, Minsk
D. V. Kazak
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Russian Federation
Russian Federation
Diana V. Kazak - Chemical Engineer.
13, Surganov Str., 220072, Minsk
E. A. Dikusar
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Russian Federation
Russian Federation
Evgenij A. Dikusar - Ph. D. (Chemistry), Senior Researcher.
13, Surganov Str., 220072, MinskR. S. Alekseev
Lomonosov Moscow State University
Russian Federation
Russian Federation
Roman S. Alekseev - Ph. D. (Chemistry), Senior Researcher.
1/3, Leninskie Gory, 119991, Moscow
N. A. Bumagin
Lomonosov Moscow State University
Russian Federation
Russian Federation
Nikolay A. Bumagin - D. Sc. (Chemistry), Professor, Leading Researcher.
1/3, Leninskie Gory, 119991, Moscow
V. I. Potkin
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Russian Federation
Russian Federation
Vladimir I. Potkin - Corresponding Member of the National Academy of Sciences of Belarus, D. Sc. (Chemistry), Professor, Head of the Department.
13, Surganov Str., 220072, MinskReferences
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