Synthesis, structure, and analgesic activity of methyl (3R*,4S*)-4-aryl-2-oxo-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates

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Abstract

A series of new methyl (3R*,4S*)-4-aryl-2-oxo-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates was obtained by three-component condensation of dimethyl malonate, aromatic aldehyde, and 1H-benzimidazole-2-amine in methanol in the presence of piperidine. The structure of the obtained compounds was determined by 1H, 13C NMR spectroscopy and X-ray diffraction analysis. The analgesic activity of the synthesized compounds was studied.

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About the authors

K. V. Podchezertseva

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

Email: tanyapgfa@yandex.ru
ORCID iD: 0009-0009-7473-5505
Russian Federation, 614990, Perm

N. A. Buzmakova

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

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0003-3171-0438
Russian Federation, 614990, Perm

T. M. Zamaraeva

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

Author for correspondence.
Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0002-9932-9628
Russian Federation, 614990, Perm

N. V. Slepova

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

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0003-3924-3715
Russian Federation, 614990, Perm

М. V. Dmitriev

Perm State National Research University

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, 614068, Perm

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2. Scheme 1. Ar = 4-BrC6H4 (1), 4-(CH3)2NC6H4 (2), 4-(C2H5)2NC6H4 (3), 3-NO2C6H4 (4), 4-CH3OC6H4 (5), 2,4-(CH3O)2C6H3 (6).

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3. Fig. 1. General view of the dimer molecule of compound 2 according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

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