Synthesis, characterization and antifungal activity of 2-[(8-hydroxyquinolinyl)-5-aminomethyl]-3-(4-chlorophenyl)-6-bromo-3(h)-quinazolin-4-one ligand and its transition metal chelates

Abstract

Synthesis and characterization of 2-[(8-hydroxyquinolinyl)-5-aminomethyl]-3-(4-chlorophenyl)-6-Bromo-3(H)-quinazolin-4-one ligand called HAMQ (HL₁₀) was studied_. To prepare this ligand anthranilic acid was converted into 5-bromo–N-Chloroacetyl anthranilic acid then into 2-[(8-hydroxyquinolinyl) -5-aminomethyl] -3-(4-chrolophenyl) -6-bromo- 3(H)-quinazolin-4-one. This compound was prepared by condensation with 5-amino-8-hydroxyquinoline. New transition metal chelates of Cu²⁺,Ni²⁺, Zn²⁺, Mn²⁺ and Co²⁺ of this ligand HAMQ  were  prepared and  characterized  by reflectance, ¹H-NMR as well as IR spectroscopy, elemental analysis molar conductance and magnetic measurements. The stoichiometry of the complexes has been found to be 1: 2 (Metal: ligand). The data suggested an octahedral geometry around Co²⁺, Ni²⁺ and Mn²⁺ complexes, a distorted octahedral geometry around Cu²⁺ and a tetrahedral geometry around Zn²⁺ have been proposed. The metal complexes were screened for the antifungal activity.

Keywords: Ligand, 8-hydroxyquinoline, IR and NMR spectral studies, antifungal activity.