Metal complexes of [1,2,4]triazolo-[1,5-a]pyrimidine derivatives

Salas, Juan M.; Romero, M. Angustias; Sánchez, María Teresa Lavado; Quirós, Miguel

doi:10.1016/s0010-8545(99)00004-1

Cited by 124 publications

(62 citation statements)

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“…Between them, 1,2,4-triazole- [1,5-a]pyrimidine (tp) derivatives are particularly studied because they are isomers of purines, and their coordination compounds can be considered as model systems for metal-ligand interactions observed in biological systems [1]. Triazolopyrimidines are versatile ligands for metal ions, the resulting complexes giving rise to a variety of structures including homo-and hetero-polynuclear compounds [1,2].…”

Section: Introductionmentioning

confidence: 99%

“…Triazolopyrimidines are versatile ligands for metal ions, the resulting complexes giving rise to a variety of structures including homo-and hetero-polynuclear compounds [1,2]. Further interest in the field comes from the search of new compounds with antimicrobial activity [1]. Many transition metal complexes of triazolopyrimidines were so far studied, while no work has been reported, to our knowledge, on their organotin(IV) derivatives, despite the ascertained biocide properties of organotin(IV) compounds [3].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

Girasolo

Salvo

Schillaci

et al. 2005

Journal of Organometallic Chemistry

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Tri-organotin(IV) complexes of the triazolo-pyrimidine derivatives 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5a]pyrimidine (5HtpO), 4,7-dihydro-5-methyl-7-oxo-[1,2,4]triazolo-[1,5a]pyrimidine (HmtpO), and 4,5,6,7-tetrahydro-5,7-dioxo-[1,2,4]triazolo-[1,5a]pyrimidine (H 2 tpO 2 ), and the diorganotin derivative n-Bu 2 Sn(tpO 2 ), were synthesized and characterized by means of infrared and 119 Sn Mö ssbauer spectroscopy. In all the complexes obtained the triazolopyrimidines act as multidentate ligands producing polymeric structures.A trigonal bipyramidal arrangement of the ligands around the tin atom is proposed for triorganotin(IV) derivatives, with organic groups on the equatorial plane and bridging anionic ligands.DFT calculations were performed on the structure of H 2 tpO 2 and on its mono-an di-anions, to investigate their harmonic vibrational modes. The observed trend of the experimental and calculated carbonyl stretching frequencies furnishes a support for the interpretation of the structure of the organotin(IV) complexes obtained with this ligand.The structure of n-Bu 2 Sn(tpO 2 ) was elucidated by quantum chemical calculations, performed on a model system of the polymeric complex by a two layers ONIOM method. The combined experimental and theoretical results obtained support for a trans-n-Bu 2 distorted octahedral geometry, with the tpO 2À 2 units acting as bis-chelate ligands bridging the diorganotin(IV) moieties, and with the N(1)O(7) and N(4)O(5) chelating groups in the equatorial plane showing a cis-O 2 , or cis-N 2 , coordination.In vitro antimicrobial tests were performed on n-Bu 3 Sn(HtpO 2 ) and Ph 3 Sn(HtpO 2 ), and a good antifungal and antibiofilm activity was observed, in particular for n-Bu 3 Sn(HtpO 2 ).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

Girasolo

Salvo

Schillaci

et al. 2005

Journal of Organometallic Chemistry

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“…The 7-amino-2-(methylthio) [1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid was a May-bridge (UK) product commercialized by C. Erba. University of Padua (Italy); tin was gravimetrically determined as SnO 2 .…”

Section: Methodsmentioning

confidence: 99%

“…Introduction [1,2,4]Triazolo [1,5-a]pyrimidine derivatives have been extensively used in the synthesis of metal-ion complexes obtaining a variety of new compounds with interesting structural features and relevant biological properties [1,2]. Organotin(IV) complexes were also recently investigated [3,4].…”

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confidence: 99%

“…Carboxylate and amino groups may play an important role in the coordination of organotin(IV) moieties, triorganotin(IV) carboxylates being arousing considerable interest owing to the variety of structures that they may originate [5] and their biological activity [6][7][8][9][10][11][12][13]. Considering the important biological role played by triazolopyrimidines, we decided to investigate the biological and coordinating properties of 7-amino-2-(methylthio) [1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid (HL) complexes with triorganotin(IV) moieties. No literature data were so far reported on this ligand; its structural formula is shown in Fig.…”

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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

Ruisi

Canfora

Brunò

et al. 2010

Journal of Organometallic Chemistry

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Structurally Different Dinuclear Copper(II) Complexes with the Same Triazolopyrimidine Bridging Ligand

Haj¹,

Quirós²,

Salas³

et al. 2002

Eur. J. Inorg. Chem.

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Keywords: Copper / N,O ligands / Metal-metal interactions / Structure elucidationFour binuclear copper(II) compounds with the anionic form of the ligand 4,5-dihydro-5-oxo[1,2,4]triazolo[1,5-a]pyrimidine (5tpO − ) have been isolated, their formulae being(3), and [Cu 2 (CH 3 CO 2 ) 2 (5tpO) 2 (H 2 O) 2 ] (4) (phen = 1,10-phenanthroline, biim = bisimidazole). A related mononuclear complex, [Cu(phen) 2 (5HtpO) 2 ](NO 3 ) 2 (5), has also been prepared. The crystal structure of compounds 1−3 has been determined by X-ray diffraction, showing their binuclear nature with four (1) or two (2, 3) bridging 5tpO − moieties. The triazolopyrimidine ligand binds the copper atoms through N3 and N4 in compounds 1 and 3, whereas a novel binding mode through N3 and the exocyclic oxygen atom has been found

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Metal complexes of [1,2,4]triazolo-[1,5-a]pyrimidine derivatives

Cited by 124 publications

References 50 publications

Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

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

Structurally Different Dinuclear Copper(II) Complexes with the Same Triazolopyrimidine Bridging Ligand

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