The Synthesis, Characterization, and Biological Activity Studies of Pt(Ii) and Pd(Ii) Disubstituted Arylcy Anoximates

Date of Graduation

Spring 2005

Degree

Master of Science in Chemistry

Department

Chemistry and Biochemistry

Committee Chair

Nikolay Gerasimchuk

Abstract

A series of six new arylcyanoximes was synthesized and characterized by spectroscopic (NMR 1H, 13C, 2D and variable temperature techniques), IR, UV/Visible) methods and x-ray crystallography. The ligands were obtained using in situ nitrosation of the respective acetonitriles by methyl nitrite under basic conditions in iso-propanol at room temperature and under an inert gas protection. This is a new class of organic acids of the general formula OH-N=C(CN)-R, where R is a disubstituted halogenated phenyl group. Halogens are F and Cl in 2,4-, 2,5-, and 2,6- positions. Crystal structures of four out of six arylcyanoximes were determined. Structures of several products of important side reactions were obtained as well. Synthesized disubstituted halogenated arylcyanoximes represent excellent ligands and form coordination compounds with monovalent Tl, Ag, and bivalent Pd, Pt. Seven complexes of the latter transition metals were tested for their anti-proliferation activity in vitro experiments using the human colon cancer cell line WiDr. The results indicated that all comples were active at high concentrations (0.25, 0.50 mM), but not as active as positive control cisplatin at low concentrations (0.01, 0.10 mM). Both Pd(II) and Pt(II) complexes of 2,4-dichlorophenyl cyanoxime showed promising cytotoxicity and were selected for further testing.

Keywords

cyanoxime, platinum, palladium, anticancer activity, coordination chemistry

Subject Categories

Chemistry

Copyright

© Leon J. Goeden

Citation-only

Dissertation/Thesis

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