Antileishmanial activity study and theoretical calculations for 4-amino-1,2,4-triazole derivatives

Süleymanoğlu N., Ünver Y., Ustabas R., Direkel Ş., Alpaslan G.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1144, ss.80-86, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1144
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.molstruc.2017.05.017
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.80-86
  • Anahtar Kelimeler: 4-amino-1,2,4-triazole, DFT calculations, NMR chemical shifts, FT-IR vibrational frequencies, Antileishmanial activity, 1,3,4-OXADIAZOLE, HYDRAZONE, NMR
  • Gazi Üniversitesi Adresli: Evet

Özet

4-amino-1,2,4-triazole derivatives; 4-amino-1-((5-mercapto-1,3,4-oxadiazole-2-yl)methyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (1) and 4 -amino-1-((4-amino-5 mercapto-4H-1,2,4triazole-3-yl)rnethyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (2) were studied theoretically by Density Functional Theory (DFT) method with 6-311++G(d,p) basis set, structural and some spectroscopic parameters were determined. Significant differences between the experimental and calculated values of vibrational frequencies and chemical shifts were explained by the presence of intermolecular (S-H center dot O and S-H center dot center dot N type) hydrogen bonds in structures. The Molecular Electrostatic Potential (MEP) maps obtained at B3LYP/6-311G++(d,p) support the existence of hydrogen bonds. Compounds were tested against to Leishmania infantum promastigots by microdilution broth assay with Alamar Blue Dye. Antileishmanial activity of 4-amino-1,2,4-triazole derivative (2) is remarkable. (C) 2017 Elsevier B.V. All rights reserved.