Synthesis, structural characterization, and biological evaluation of oxorhenium(V) complexes with a novel type of thiosemicarbazones derived from N-[N',N'-dialkylamino(thiocarbonyl)]benzimidoyl chlorides.
Reactions of N-[N',N'-diethylamino(thiocarbonyl)]benzimidoyl chloride with 4,4-dialkylthiosemicarbazides give a novel class of thiosemicarbazides/thiosemicarbazones, H(2)L, which causes a remarkable reduction of cell growth in in vitro experiments. These strong antiproliferative effects are also observed for oxorhenium(V) complexes of the general composition [ReOCl(L)], which are formed by reactions of the potentially tridentate ligands with (NBu(4))[ReOCl(4)]. A systematic substitution of the alkyl groups in the thiosemicarbazone building blocks of the ligands do not significantly influence the biological activity of the metal complexes, while the replacement of the chloro ligand by a PPh(3) ligand (by the replacement of the oxo unit by a nitrido ligand) completely terminated the cytotoxicity of the metal complexes.
Nguyen
Hung Huy
HH
Department of Chemistry, Hanoi University of Sciences, 19 Le Thanh Tong, Hanoi, Vietnam.
Jegathesh
Jesudas J
JJ
Maia
Pedro I da S
PI
Deflon
Victor M
VM
Gust
Ronald
R
Bergemann
Silke
S
Abram
Ulrich
U
D045744:Cell Line, Tumor; D002712:Chlorides / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008024:Ligands; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D015609:Organotechnetium Compounds / Q000737:chemistry / Q000494:pharmacology; D012211:Rhenium / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D002712:Chlorides; D008024:Ligands; D015609:Organotechnetium Compounds; D013882:Thiosemicarbazones; C015428:perrhenate; D012211:Rhenium