Nitrogen, sulfur and oxygen donor adducts with copper(II) complexes of antitumor 2-formylpyridinethiosemicarbazone analogs: physicochemical and cytotoxic studies.
The preparation of N-, S- and O-donor ligand adducts with CuX+ (HX = 6-methyl-2-formylpyridinethiosemicarbazone (6HL); 2-formylpyridine-2'-methylthiosemicarbazone (2'L); 2-formylpyridine-4'-methylthiosemicarbazone (4'HL) is described. The N-donors, 2,2'-bipyridyl (bipy), 4-dimethylaminopyridine (dmap) give the complexes [Cu(6L)(bipy)]PF6, [Cu(6L)(bipy)]Cl.5H2O, [Cu(4'L)(bipy)]PF6, [Cu(6L)(dmap)2]PF6.2.5 H2O and [Cu(4'L)(dmap)2]PF6.H2O which have been characterized by physical and spectroscopic techniques. Pentafluorothiophenolate (pftp) gives S-donor complexes [CuX(pftp)] (X = 6L and 4'L) and thiolato co-ordination is proposed on the basis of spectroscopic evidence. Paratritylphenolate (ptp) and HPO4(2-) give O-donor complexes [Cu(6L)(ptp)], [Cu(4'L)(ptp)], [¿Cu(6L)¿2HPO4].4H2O, and [¿Cu(4'L)¿2HPO4].5H2O which have been characterized by physical and spectroscopic techniques, as have the precursor complexes [Cu(6L)(CH3COO)].H2O, [Cu(4'L)(CH3COO)], Cu(6HL)(CF3COO)](CF3COO).0.5H2O, [Cu(4'HL)(CF3COO)](CF3COO), [Cu(2'L)Cl2) and [Cu(2'L)(NO3)2]. Protonation constants for the ligands and some of their complexes have been determined. 2-Formylpyridinethiosemicarbazone (HL) complexes of silver, gold, zinc, mercury, cadmium and lead are also discussed. Cytotoxicity against the human tumor cell line HCT-8 and antiviral data for selected compounds are presented.
Ainscough
E W
EW
Chemistry-Institute of Fundamental Sciences, Massey University, Palmerston North, New Zealand.
Brodie
A M
AM
Denny
W A
WA
Finlay
G J
GJ
Ranford
J D
JD
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology; D003110:Colonic Neoplasms / Q000188:drug therapy; D004354:Drug Screening Assays, Antitumor; D004563:Electrochemistry / Q000379:methods; D006801:Humans; D008958:Models, Molecular; D009584:Nitrogen / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry; D013053:Spectrophotometry; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009942:Organometallic Compounds; D013882:Thiosemicarbazones; C013996:2-formylpyridine thiosemicarbazone; D013455:Sulfur; D009584:Nitrogen; D010100:Oxygen