Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography

Giuseppe Ruisi, Bartolomeo Megna, Maria Assunta Girasolo, Loredana Canfora, Giuseppe Bruno, Teresa F. Mastropietro, Eugenio A. Debbia, Archimede Rotondo

Risultato della ricerca: Articlepeer review

32 Citazioni (Scopus)

Abstract

Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylicacid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting theamino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterizedby elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn Mössbauer spectroscopictechniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH)presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axialpositions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule,MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopicdata. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similartbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axiallybridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordinationspheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and awater molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity againstGram-positive bacteria.
Lingua originaleEnglish
pagine (da-a)546-551
Numero di pagine6
RivistaJournal of Organometallic Chemistry
Volume695
Stato di pubblicazionePublished - 2010

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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