Synthesis and biological activity of substituted 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides

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Abstract

A four-component solvent-free reaction of acetoacetic acid amide with dimedone, aromatic aldehydes and ammonium acetate leads to new substituted 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides. The structures of the products were proved using IR, 1H and 13C NMR spectroscopy, mass spectrometry and X-ray diffraction analysis. The synthesized compounds were tested for antimicrobial and antinociceptive activities.

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About the authors

N. V. Nosova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Author for correspondence.
Email: geinvl48@mail.ru
ORCID iD: 0000-0001-6380-2543
Russian Federation, Perm

М. О. Starovoytova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
Russian Federation, Perm

R. R. Mahmudov

Perm State National Research University; Federal Scientific Center for Medical and Preventive Health Risk Management Technologies

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-2326-3976
Russian Federation, Perm; Perm

V. V. Novikova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
Russian Federation, Perm

М. V. Dmitriev

Perm State National Research University

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, Perm

V. L. Gein

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8512-0399
Russian Federation, Perm

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Supplementary files

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2. Scheme 1. R = Ph (5a), 4-FC6H4 (5б), 2-FC6H4 (5в), 4-ClC6H4 (5г), 2-ClC6H4 (5д), 4-BrC6H4 (5е), 2-BrC6H4 (5ж), 3-NO2C6H4 (5з), 4-MeC6H4 (5и), 4-EtC6H4 (5к), 4-i-PrC6H4 (5л), 4-i-BuC6H4 (5м), 4-MeOC6H4 (5н), 3-C5H4N (5о), 4-NO2C6H4 (5п).

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3. Scheme 2.

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4. Scheme 3.

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5. Fig.1. General view of the molecule of compound 5z in a crystal, represented by thermal ellipsoids with a 30% probability.

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