Sintesi, caratterizzazione strutturale e attività biologica in vitro di organostagno(IV) con derivati di 1,2,4-triazolo[1,5-a]pirimidina

Research output: Contribution to conferenceOther

Abstract

[automatically translated] SYNTHESIS, STRUCTURAL CHARACTERIZATION AND BIOLOGICAL ACTIVITY IN VITRO organotin (IV) WITH DERIVATIVES OF 1,2,4-triazole [1, 5-a] pyrimidine Maria Assunta in Girasolo, Simona Rubino in, Piera Sabatino b aDip.to of Science and Molecular and Biomolecular technologies, University of Palermo, Viale delle Scienze, Palermo, Italy bDip.to G. Ciamician Chemistry, University of Bologna, via F. Selmi 2, Bologna, Italy the structure of 1,2,4-triazole [1 , 5-a] pirimidine1 is analogous to that of purines from which differ in the presence of a nitrogen atom of the pyrimidine ring in position "bridgehead" and the disappearance of the proton acid to five ring members. Given the similarity between these systems, the coordination compounds of the 1,2,4-triazolo- [1,5-a] pyrimidines can be considered as model systems for various existing coordination compounds in nature. There have recently been synthesized and characterized, some compounds of diorganostagno (IV) with 5,7-diphenyl-1,2,4-triazolo [1,5-a] pyrimidine2 (DPTP), of which the following is the X-ray structure, and with the 7-amino-2- (methylthio) - [1,2,4] triazolo [1,5-a] pyrimidine-6-carboxylic acid. Figure 1: crystalline and molecular structure of the adduct [n-Bu2SnCl2 (DPTP)] (1) Compound (1) has a distorted trigonal bipyramidal coordination around the atom of Sn; DPTP the binder, which binds via N (3), occupies the trans position with respect to one of the two atoms of Cl while the three equatorial positions are occupied by the remaining Cl atom and the two n-butyl binders. The three-dimensional packing of the molecule is characterized by both a network of H-bonds between the CH groups and Cl atoms from both aromatic interactions between the aromatic rings present. The cytotoxic activity of (1) was tested on U937 human histiocytic lymphoma cell line. The cells were treated for 24 h in a concentration range of between 0.5-20 uM adduct (1), in comparison to cisplatin. The results obtained showed that at a concentration of 20 uM, n-Bu2SnCl2 (DPTP) induces a marked reduction in cell viability which results to be of 5.5%, much lower value of the cisplatin, that at the same concentration is of 44%. The compound is therefore more active than cisplatin. The complexes R2SnL2 were obtained by reaction of R2SnO (R = Me, n-Bu, n-Oct) with the 7-amino-2- (methylthio) - [1,2,4] triazolo [1,5-a] pyrimidine-6-carbossilico3 (HL) in refluxing methanol. The nature of the products obtained was investigated by analyzing the spectroscopic data 1H-NMR, IR and Mössbauer 119Sn. Examining the Mössbauer parameters we can observe that the quadrupole splitting values are larger than the values observed in complex diorganostagno (IV) with tetrahedral geometry. We must therefore assume that the pond expand the coordination number resulting in trigonal bipyramidal structures, cis or trans-R2, or octahedral trans-R2 highly distorted. Bibliography 1Salas, JM, Romero, MA; Sánchez, MP; Quirós, M., Coord. Chem. Rev., 1999,1119,193. 2Girasolo, MA; camphor, L.; Sabatino, P.; Schillaci, D.; Foresti, E., Ruby, S.; Ruisi, G.; Stocco, G., J.Inorg.Biochem., 2012,106,156. 3Ruisi, G., Camphor, L.; Brown, G .; Round, A.; Mastropietro, TF; Debbia, EA; Girasolo, MA; Megna, B., J.Organomet. Chem., 2010,695,546.
Original languageItalian
Number of pages91
Publication statusPublished - 2012

Cite this