Synthesis, biological activities, and crystal structure of 1,2,4-triazole-5-one-based benzenesulfonamides

SANCAK K., Kilinc G. G., Durak F., Ozsanli H., Çoruh U., BARUT B.

JOURNAL OF MOLECULAR STRUCTURE, vol.1339, 2025 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1339
  • Publication Date: 2025
  • Doi Number: 10.1016/j.molstruc.2025.142414
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, firstly the ring closed reaction of hydrazine carboxylates (2) with 3-(2 aminoethyl) benzene sulfonamide (1) in a thermally controlled reaction afforded 4-(2-(3-alkyl/alkylaryl/aryl-5-oxo-1,5-dihydro-4H1,2,4-triazol-4-yl) ethyl) (3a-g) sulfonamide derivative 1,2,4-triazol-5-one compounds. The synthesized compounds were characterized using FT-IR, 1H-NMR and 13C-NMR spectra. In the second step, inhibition studies of acetylcholinesterase, butyrylcholinesterase alpha-glycosidase and tyrosinase were performed to determine the inhibitory properties of the compounds. In antimicrobial tests against 13 different microorganisms, it was determined that the compounds were selectively effective against the Bacillius Cereus pathogen. Antioxidant activity tests were performed in the part of the study, moderate radical scavenging properties were determined in all compounds except 3a and 3g. XRD analysis was performed to determine the structural parameters of the single crystal (3d) and to reveal the crystallographic structure information.