Synthesis, characterization and cytotoxity of Pd(II), Pt(II) and Pt(IV) complexes with R2edda-type esters

[B. Zmejkovski]

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Hemija - neorganska hemija / Chemistry - inorganic chemistry

U ovom radu su opisane sinteze, karakterizacija i antiproliferativna aktivnost liganada u obliku hidrohloridnih soli, estara etilendiamin-N,N’-di-3-propanske kiseline (H2eddp), (S,S)-etilendiamin-N,N’-di-2-propanske kiseline ((S,S)-H2eddip) i (S,S)-etilendiamin-N,N’-di-2-(4-metil)-pentanske kiseline ((S,S)-H2eddl), kao i odgovarajućih kompleksa sa platinom(IV), platinom(II) i paladijumom(II). Sintetisano je osam novih estara, a to su izopropil i izobutil estri svih navedenih kiselina, a sa (S,S)-H2eddip dobijeni su i ciklopentil i cikloheksil estri. Ova jedinjenja su dobijena refluktovanjem suspenzije kiseline u odgovarajućem apsolutnom alkoholu kome je prethodno ukapan tionil-hlorid. Svi estri su dobijeni u obliku dihidrohlorida: [(S,S)-H2iPr2eddip]Cl2, [(S,S)-H2iBu2eddip]Cl2, [(S,S)-H2cPe2eddip]Cl2, [(S,S)-H2Cy2eddip]Cl2, [H2iPr2eddp]Cl2, [H2iBu2eddp]Cl2, [(S,S)-H2iPr2eddl]Cl2 i [(S,S)-H2iBu2eddl]Cl2. Estri su okarakterisani elementalnom analizom, infracrvenom i NMR spektroskopijom, a [(S,S)-H2iPr2eddip]Cl2, [(S,S)-H2cPe2eddip]Cl2 i [(S,S)-H2iBu2eddl]Cl2 urađena je i rendgenostrukturna analiza. U pokušaju sinteze ciklopentil estra (S,S)-etilendiamin-N,N'-di-2-(3-metil)-butanske kiseline (S,S)-H2eddv, dobijeni su neočekivani monokristali sastava [(S,S)-H4eddv]Br0,17Cl1,83.4C5H9OH. Kompleksi platine(IV) dobijeni su u reakciji natrijum- ili kalijum-heksahloroplatinata(IV) sa navedenim estrima. Sintetisano je pet novih kompleksa platine(IV): [PtCl4{(S,S)-iPr2eddip}], [PtCl4{(S,S)-iBu2eddip}], [PtCl4{(S,S)-cPe2eddip}], [PtCl4(iPr2eddp)] i [PtCl4(iBu2eddp)]. Ovi kompleksi su okarakterisani elementalnom analizom, infracrvenom i NMR spektroskopijom. Kristalna struktura određena je kompleksima [PtCl4{(S,S)-iPr2eddip}] i [PtCl4{(S,S)-cPe2eddip}]. Kompleksi platine(II) dobijeni su u reakciji kalijum-tetrahloroplatinata(II) sa estrima. Sintetisano je tri nova kompleksa platine(II): [PtCl2{(S,S)-iPr2eddip}], [PtCl2{(S,S)-iBu2eddip}] i [PtCl2{(S,S)-cPe2eddip}]. Ovi kompleksi su okarakterisani elementalnom analizom, infracrvenom i NMR spektroskopijom. Sedam novih kompleksa paladijuma(II): [PdCl2{(S,S)-iPr2eddip}], [PdCl{(S,S)-iPreddip}], [PdCl2{(S,S)-iBu2eddip}], [PdCl2{(S,S)-cPe2eddip}], [PdCl2{(S,S)-Cy2eddip}], [PdCl2{(S,S)-iPr2eddl}] i [PdCl2{(S,S)-iBu2eddl}] dobijeno je u reakciji kalijum-tetrahloropaladata(II) sa estrima. Ovi kompleksi su okarakterisani elementalnom analizom, infracrvenom i NMR spektroskopijom...

This work describes synthesis, characterization and antiproliferative activity of ligands precursors, esters of ethylenediamine-N,N’-di-3-propanoic acid (H2eddp), (S,S)-ethylenediamine-N,N’-di-2-propanoic acid ((S,S)-H2eddip) and (S,S)-ethylenediamine-N,N’-di-2-(4-methyl)-pentanoic acid ((S,S)-H2eddl), as well as their complexes with platinum(IV), platinum(II) and palladium(II). Eight novel esters are synthesized, isopropyl and isobutyl esters of the mentioned acids, and cyclopentyl and cyclohexyl esters of (S,S)-H2eddip. Thionyl-chloride was intoduced into a flask containing absolute alcohol. The corresponding acid is added forming a suspension which was reflucted. All of the esters were obtained as dihydrochlorides: [(S,S)-H2iPr2eddip]Cl2, [(S,S)-H2iBu2eddip]Cl2, [(S,S)-H2cPe2eddip]Cl2, [(S,S)-H2Cy2eddip]Cl2, [H2iPr2eddp]Cl2, [H2iBu2eddp]Cl2, [(S,S)-H2iPr2eddl]Cl2, [(S,S)-H2iBu2eddl]Cl2. Esters were characterized by elemental analysis, IR and NMR spectroscopy. Crystal structures of [(S,S)-H2iPr2eddip]Cl2, [(S,S)-H2cPe2eddip]Cl2 and [(S,S)-H2iBu2eddl]Cl2 are solved by X-ray analyses. While trying to synthesize the cyclopentyl ester of (S,S)-ethylenediamine-N,N'-di-2-(3-methyl)-butanoic acid (S,S)-H2eddv, unexpected crystals suitable for X-ray analysis were obtained and determined - [(S,S)-H4eddv]Br0.17Cl1.83.4C5H9OH. Complexes of platinum(IV) are synthesized in a reaction of potassium-hexachloroplatinate(IV) with esters. Five novel platinum(IV) complexes are obtained: [PtCl4{(S,S)-iPr2eddip}], [PtCl4{(S,S)-iBu2eddip}], [PtCl4{(S,S)-cPe2eddip}], [PtCl4(iPr2eddp)] and [PtCl4(iBu2eddip)]. These complexes are characterized by elemental analysis, IR and NMR spectroscopy...

platina(IV) kompleksi, platina(II) kompleksi, paladijum(II) kompleksi, R2edda ligandi, kristalna struktura, DFT proračuni, antiproliferativna aktivnost

platinum(IV) complexes, platinum(II) complexes, palladium(II) complexes, R2edda-type ligands, crystal structure, DFT calculations, antiproliferative activity

546.9-386:577.11(043.3)

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