Synthesis and Some Regularities of Transformations of 5,5-Dimethyl-3-(2-methylalyl)-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one. Antibacterial Activity of the Obtained Compounds
- Autores: Markosyan A.1, Ayvazyan A.1, Gabrielyan S.1, Danghyan M.1, Avakimyan J.1, Arsenyan F.1
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Afiliações:
- Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
- Edição: Volume 94, Nº 3 (2024)
- Páginas: 376-384
- Seção: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/261506
- DOI: https://doi.org/10.31857/S0044460X24030083
- EDN: https://elibrary.ru/FYVFMI
- ID: 261506
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Resumo
Based on ethyl 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate (amino ester), a method for the synthesis of 5,5-dimethyl-3-(2-methylallyl)-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one was developed. The latter was alkylated with halides of various structures, resulting in the production of 2-alkylsulfanyl-5,5-dimethyl-3-(2-methylallyl)-5, 6-dihydrobenzo[h]quinazoline-4(3H)-ones. By condensation of thioxobenzoquinazoline with hydrazine hydrate, 2-hydrazinyl-5,5-dimethyl-3-(2-methylallyl)-5,6-dihydrobenzo[h]quinazoline-4(3H)-one was synthesized, but similar reactions with 2-ethanolamine and 3-propanolamine proceeded abnormally with the formation of 2-(2-hydroxyethyl)amino-5,5-dimethyl-5,6-dihydrobenzo[h]quinazoline-4(3H)-one and 2-(3-hydroxypropyl)amino-5,5-dimethyl-5,6-dihydrobenzo[h]quinazoline-4(3H)-one, respectively. The interaction of the indicated thioxobenzoquinazoline with benzylamine proceeds with intramolecular cyclization with the formation of 6,6,10,10-tetramethyl-9,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazoline-7(6H)-one. The antibacterial properties of the synthesized compounds were studied. It was found that the studied compounds have antibacterial activity.
Texto integral
Sobre autores
A. Markosyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: ashot@mаrkosyan.am
ORCID ID: 0000-0001-6665-7118
Rússia, Yerevan, 0014 Armenia
A. Ayvazyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: nfo@rcsi.science
ORCID ID: 0000-0001-8384-7431
Rússia, Yerevan, 0014 Armenia
S. Gabrielyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: nfo@rcsi.science
Rússia, Yerevan, 0014 Armenia
M. Danghyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: nfo@rcsi.science
Rússia, Yerevan, 0014 Armenia
J. Avakimyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Email: nfo@rcsi.science
Rússia, Yerevan, 0014 Armenia
F. Arsenyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Autor responsável pela correspondência
Email: nfo@rcsi.science
Rússia, Yerevan, 0014 Armenia
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