Abstract
Two new Schiff and Mannich bases, namely, 1-Morpholinomethyl-3(1′ -N-dithiooxamide)iminoisatin (LIH) and 1-diphenylaminomethyl-3-1′-N-dithiooxamide)iminoisatin (LIIH), were prepared from condensation reaction of new Schiff base 3-(1′-N-dithiooxamide)iminoisatin (SBH) with morpholine or diphenylamine respectively in presence of formaldehyde . The structures were characterized by IR, 1HNMR, mass spectrometry, and CHN analyses. Metal complexes of the two ligands were synthesized, and their structures were characterized by elemental analyses, atomic absorption, IR and UV-visible spectra, molar conductivity, and magnetic moment determination. All complexes showed octahedral geometries except palladium complexes which were square planar. The biological activity of the prepared compounds and some selected metal complexes was tested against three types of bacteria and against cell line of human epidermoid larynx carcinoma (Hep-2).
Highlights
Various Mannich Schiff bases of isatin have been found to be of biological importance [1] and have shown anticonvulsant [2], antibacterial [3, 4], antimicrobial [5,6,7] and anti-HIV activities [8, 9]
The aim of this work is to synthesize and study the coordination behavior of the two new Schiff and Mannich base ligands LIH and LIIH shown in Scheme 1, from condensation reaction of a new Schiff base 3(1 -N-dithiooxamide) iminoisatin (SBH) with morpholine or diphenylamine, respectively, in presence of formaldehyde in a mole ratio of (1 : 1 : 1), respectively, or from reaction of Mannich bases N-morpholinomethyl isatin (MI) and Ndiphenylaminomethyl isatin (MII) [16] with dithiooxamide
Pathway A involves the synthesis of Schiff base precursor of isatin (SBH) followed by condensation with the secondary amine, morpholine or diphenylamine, in presence of formaldehyde to form LIH and LIIH, respectively
Summary
Various Mannich Schiff bases of isatin have been found to be of biological importance [1] and have shown anticonvulsant [2], antibacterial [3, 4], antimicrobial [5,6,7] and anti-HIV activities [8, 9]. Dithiooxamide (dto) is an effective flexidentate complexing agent with varied coordination chemistry. Due to the intense chromophoric character, dto can be used in an imaging processes [10], coordination polymers [11], histological agents, and as a source for duplicating processes [12]. The biological activity of the two ligands and some of their metal complexes was investigated against selected types of bacteria and against cancer cell line of human epidermoid larynx carcinoma (Hep-2) The aim of this work is to synthesize and study the coordination behavior of the two new Schiff and Mannich base ligands LIH and LIIH shown in Scheme 1, from condensation reaction of a new Schiff base 3(1 -N-dithiooxamide) iminoisatin (SBH) with morpholine or diphenylamine, respectively, in presence of formaldehyde in a mole ratio of (1 : 1 : 1), respectively, or from reaction of Mannich bases N-morpholinomethyl isatin (MI) and Ndiphenylaminomethyl isatin (MII) [16] with dithiooxamide.
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