| Journal: | Anais da Academia Brasileira de Ciencias |
| Database: | PERIÓDICA |
| System number: | 000419766 |
| ISSN: | 0001-3765 |
| Authors: | Sirakanyan, Samvel N1 Geronikaki, Athina2 Spinelli, Domenico3 Hakobyan, Elmira K1 Kartsev, Viktor G4 Petrou, Anthi2 Hovakimyan, Anush A1 |
| Institutions: | 1National Academy of Science of Republic of Armenia, Scientific Technological Center of Organic and Pharmaceutical Chemistry, Yerevan. Armenia 2Aristotle University of Thessaloniki, School of Pharmacy, University Campus, 54124, Thessaloniki. Grecia 3"Alma Mater Studiorum" Universita di Bologna, Dipartimento di Chimica, Bolonia, Emilia Romaña. Italia 4InterBioScreen, Moscú. Rusia |
| Year: | 2018 |
| Season: | May |
| Volumen: | 90 |
| Number: | 1 |
| Pages: | 1043-1057 |
| Country: | Brasil |
| Language: | Inglés |
| Document type: | Artículo |
| Approach: | Experimental, aplicado |
| English abstract | Annulated thienopyrimidine derivatives attracted big interest of the scientific community due to their broad spectrum of biological activities among which are the inhibition of phosphodiesterase, antiproliferative and antimicrobial activities. As a continuation of our studies on the synthesis and biological activity of fused thieno[3,2-d]pyrimidine derivatives, the goal of this paper is the synthesis and study of the properties of compounds containing different heterocycles such as fused thieno[2,3-b]pyridine and tetrazolo[1,5-c]pyrimidine in the same molecule. Thus, starting from the ethyl 1-amino-5-isopropyl-8,8-dimethyl-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate 1, efficient methods for obtaining new 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidines 6 and thieno[2,3-e]tetrazolo[1,5-c]pyrimidine 8 are described. The spectroscopic results showed that compound 8 in the solid state is exclusively in the tetrazolo tautomeric form, while in solution an azide-tetrazole equilibrium is present 8A/T. The possible antimicrobial activity of newly synthesized compounds against some gram-positive and gram-negative bacilli strains has been evaluated. The biological tests evidenced that some of them showed promising antimicrobial activity. Two compounds showed similar activity to the one of the used reference drug. The study of structure-activity relationships revealed that the activity of a compound depends mostly on the nature of substituent R1R2. According to the predicted docking studies our compounds could be DnaG inhibitors |
| Disciplines: | Medicina, Química |
| Keyword: | Química farmacéutica, Microbiología, Derivados amino, Actividad antimicrobiana, Equilibrio azida-tetrazóleo, Sustitución nucleofílica, Tieno(3,2-d)pirimidina |
| Keyword: | Medicinal chemistry, Microbiology, Amino derivatives, Antimicrobial activity, Azide-tetrazole equilibrium, Nucleophilic substitution, Thieno[3,2-d]pyrimidine |
| Full text: | Texto completo (Ver HTML) |
