New organotin(IV) complexes of 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine (dbtp) and 5,7-diphenyl- 1,2,4-triazolo[1,5-a]pyrimidine (dptp) with 1:1 and/or 1:2 stoichiometry were synthesized and investigated by X-ray diffraction, FT-IR and 119Sn Mössbauer in the solid state and by 1H and 13C NMR spectroscopy, in so- lution. Moreover, the crystal and molecular structures of Et2SnCl2(dbtp)2 and Ph2SnCl2(EtOH)2(dptp)2 are reported. The complexes contain hexacoordinated tin atoms: in Et2SnCl2(dbtp)2 two 5,7-ditertbutyl-1,2,4- triazolo[1,5-a]pyrimidine molecules coordinate classically the tin atom through N(3) atom and the coordina- tion around the tin atom shows a skew trapezoidal structure with axial ethyl groups. In Ph2SnCl2(EtOH)2 (dptp)2 two ethanol molecules coordinate tin through the oxygen atom and the 5,7-diphenyl-1,2,4-triazolo [1,5-a]pyrimidine molecules are not directly bound to the metal center but strictly H-bonded, through N (3), to the \OH group of the ethanol moieties; Ph2SnCl2(EtOH)2(dptp)2 has an all-trans structure and the C–Sn–C fragment is linear. On the basis of Mössbauer data, the 1:2 diorganotin(IV) complexes are advanced to have the same structure of Et2SnCl2(dbtp)2, while Me2SnCl2(dptp)2 to have a regular all-trans octahedral structure. A distorted cis-R2 trigonal bipyramidal structure is assigned to 1:1 diorganotin(IV) complexes. The in vitro antibacterial activities of the synthesized complexes have been tested against a group of reference pathogen micro-organisms and some of them resulted active with MIC values of 5 μg/mL, most of all against staphylococcal strains, which shows their inhibitory effect.

Girasolo, M.A., Canfora, L., Sabatino, P., Schillaci, D., Foresti, E., Rubino, S., et al. (2012). Synthesis, characterization, crystal structures and in vitro antistaphylococcal activity of organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine. JOURNAL OF INORGANIC BIOCHEMISTRY, 106, 156-163 [10.1016/j.jinorgbio.2011.09.010].

Synthesis, characterization, crystal structures and in vitro antistaphylococcal activity of organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine

GIRASOLO, Maria Assunta;CANFORA, Loredana;SCHILLACI, Domenico;RUBINO, Simona;RUISI, Giuseppe;STOCCO, Giancarlo
2012-01-01

Abstract

New organotin(IV) complexes of 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine (dbtp) and 5,7-diphenyl- 1,2,4-triazolo[1,5-a]pyrimidine (dptp) with 1:1 and/or 1:2 stoichiometry were synthesized and investigated by X-ray diffraction, FT-IR and 119Sn Mössbauer in the solid state and by 1H and 13C NMR spectroscopy, in so- lution. Moreover, the crystal and molecular structures of Et2SnCl2(dbtp)2 and Ph2SnCl2(EtOH)2(dptp)2 are reported. The complexes contain hexacoordinated tin atoms: in Et2SnCl2(dbtp)2 two 5,7-ditertbutyl-1,2,4- triazolo[1,5-a]pyrimidine molecules coordinate classically the tin atom through N(3) atom and the coordina- tion around the tin atom shows a skew trapezoidal structure with axial ethyl groups. In Ph2SnCl2(EtOH)2 (dptp)2 two ethanol molecules coordinate tin through the oxygen atom and the 5,7-diphenyl-1,2,4-triazolo [1,5-a]pyrimidine molecules are not directly bound to the metal center but strictly H-bonded, through N (3), to the \OH group of the ethanol moieties; Ph2SnCl2(EtOH)2(dptp)2 has an all-trans structure and the C–Sn–C fragment is linear. On the basis of Mössbauer data, the 1:2 diorganotin(IV) complexes are advanced to have the same structure of Et2SnCl2(dbtp)2, while Me2SnCl2(dptp)2 to have a regular all-trans octahedral structure. A distorted cis-R2 trigonal bipyramidal structure is assigned to 1:1 diorganotin(IV) complexes. The in vitro antibacterial activities of the synthesized complexes have been tested against a group of reference pathogen micro-organisms and some of them resulted active with MIC values of 5 μg/mL, most of all against staphylococcal strains, which shows their inhibitory effect.
Settore CHIM/03 - Chimica Generale E Inorganica
Girasolo, M.A., Canfora, L., Sabatino, P., Schillaci, D., Foresti, E., Rubino, S., et al. (2012). Synthesis, characterization, crystal structures and in vitro antistaphylococcal activity of organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine. JOURNAL OF INORGANIC BIOCHEMISTRY, 106, 156-163 [10.1016/j.jinorgbio.2011.09.010].
File in questo prodotto:
File Dimensione Formato  
JIB 2012.pdf

accesso aperto

Descrizione: Articolo principale
Dimensione 805.77 kB
Formato Adobe PDF
805.77 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/62086
Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 23
  • ???jsp.display-item.citation.isi??? 22
social impact