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- Title
SYNTHESIS OF DIHYDROTETRAZOLOPYRIMIDINE DERIVATIVES AS ANTICANCER AGENTS AND INHIBITOR OF a-GLUCOSIDASE.
- Authors
Suwito, H.; Kurnyawaty, N.; Haq, K. U.; Ramadhan, R.; Abdulloh, A.; Hardiyanti, H. D.; Phuwapraisirisan, P.
- Abstract
A series of dihydrotetrazolopyrimidine derivatives were prepared to utilize a three-component Biginelli reaction from ethyl 3-oxo butanoate, 5-amino tetrazole, and various aromatic aldehydes as reactants, pTSA as a Brønsted acid catalyst, and ethanol as the solvent. The structure of the prepared compounds was established by spectroscopic evidence, FTIR, HRMS, and NMR (¹H- and 13C-) spectra. The electronic properties of the aromatic aldehyde's substituents affected the reaction's time and yield. Substituents possessing electron-donating character accelerated the reaction time but decreased the reaction yield, whereas substituents with electron-withdrawing properties slowed the reaction but increased the yield. The prepared compounds exhibited moderate to strong anti-proliferative activities against 4T1 and HeLa cancer cell lines. Compound Ethyl (E)-5-methyl-7-(1-phenylprop-1-en-2-yl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate and compound Ethyl 7-(1H-indol-3-yl)-5-methyl-4,7-dihydrotetrazolo[ 1,5-a]pyrimidine-6-carboxylate) showed strong anti-proliferative activities in vitro through induction apoptotic cells death mechanism. In addition, five of the synthesized compounds exhibited better inhibitory activity of a-glucosidase than quercetin, the positive control.
- Subjects
ANTINEOPLASTIC agents; AROMATIC aldehydes; ACID catalysts; QUERCETIN; BRONSTED acids; CHEMICAL synthesis; TETRAZOLES
- Publication
Rasayan Journal of Chemistry, 2023, Vol 16, Issue 1, p147
- ISSN
0974-1496
- Publication type
Article
- DOI
10.31788/RJC.2023.1618025