One-Pot Four-Component Synthesis of Substituted N-Methyl 5-Охо-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides. Biological Activity of the Obtained Compounds

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Abstract

A one-pot four-component solvent-free reaction of N-methyl acetoacetamide with dimedone, aromatic aldehyde and ammonium acetate leads to new substituted N-methyl 1,4,5,6,7,8-hexahydroquinoline-3-carboxamides. The structures of the products were proved using IR, 1H and 13C NMR spectroscopy. The synthesized compounds were tested for antimicrobial and antinociceptive activities. The resulting compounds have shown antinociceptive activity greater than that of metamizole sodium.

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About the authors

N. V. Nosova

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

Email: geinvl48@mail.ru
ORCID iD: 0000-0001-6380-2543
Russian Federation, Perm, 614990

M. O. Starovoytova

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

Email: geinvl48@mail.ru
Russian Federation, Perm, 614990

M. A. Loginova

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

Email: geinvl48@mail.ru
Russian Federation, Perm, 614990

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, 614990; Perm, 614045

V. V. Novikova

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

Email: geinvl48@mail.ru
Russian Federation, Perm, 614990

I. G. Mokrushin

Perm State National Research University

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-4095-8366
Russian Federation, Perm, 614990

V. L. Gein

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

Author for correspondence.
Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8512-0399
Russian Federation, Perm, 614990

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2. Scheme 1. R = Ph (5a), 4-ClC6H4 (5 b), 3-ClC6H4 (5 c), 2-ClC6H4 (5 g), 4-FC6H4 (5d), 4-CH3OCOS6H4 (5 e).

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3. Scheme 2.

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