Synthesis, Structural Characterization and Biological activities of Transition Metal Complexes with Quinolone ligands and Phosphoramidates

Abstract

The present study is about synthesis, characterization and biological activity of two series (A & B) compounds. Series A include complexes of transition metals with quinolone ligands and series B phosphoramidates. The series A complexes are of the general formula C44H48N8O4X2M where X= H, Cl and CH3. The series B compounds are of the general formula R2C6H5O3XP where R= -CH2-CH3, -CH(CH3)2 and –CH2-CH2-CH2-CH3 and X= H, F, Cl, Br, -CH3 and -OCH3. The obtained compounds were in a good yield and were moisture and air stable. They are soluble in common organic solvents. Various analytical techniques were used for their structure elucidation namely melting point, FT-IR, multinuclear NMR (1H, 13C, 31P) and GC-MS. The spectroscopic analysis confirmed the ligand coordination to the metal in the centers via nitrogen and oxygen in the complexes. The spectroscopic techniques agreed with symmetric bidentate binding of the ligand metal centers. Antitumor screening of the series A complexes was carried with Sodium salt of Salmon testes (D1626) found previously resistant to cisplatin. The complexes showed greater activity against some gram negative and gram positive bacteria while they have shown low antifungal activity. The viscometric studies had shown good binding potential of these complexes to DNA which may be the basis for their obvious anticancer action. For the series B compounds an optimized catalytic cost effective method of dehydrogenative coupling of dialkyl phosphite with aryl amine led to the formation of the corresponding phosphoramidates. Structures of the synthesized compounds were elucidated from FT-IR, 13C, 31P, 1H and GC-MS techniques. Series B compounds gave low antimicrobial activity.