2 Citations (Scopus)

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 (1 H-and13 C-) 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-dihydrote-trazolo[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 α-glucosidase than quercetin, the positive control.

Original languageEnglish
Pages (from-to)147-158
Number of pages12
JournalRasayan Journal of Chemistry
Volume16
Issue number1
DOIs
Publication statusPublished - 1 Jan 2023

Keywords

  • Anti-Diabetes
  • Anticancer
  • Apoptosis
  • Biginelli Reaction
  • Dihydrotetrazolopyrimidine

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