Urease inhibition and anti-leishmanial assay of substituted benzoylguanidines and their copper(ii) complexes

Abstract

A series of N,N',N''-trisubstituted guanidines (1-6) and their copper(II) complexes, [κ(2)(O,N)-C(6)H(5)CONHC(NHC(6)H(4)Cl)NR](2)Cu(ii) (R = iso-propyl (1a), n-butyl (2a), sec-butyl (3a), tert-butyl (4a), benzyl (5a), and para-tolyl (6a)) were synthesized and characterized using elemental analysis, FTIR and NMR spectroscopy. DFT studies were used to assess the location of the protons in the free ligands. However, calculations have shown that, in all cases, hydrogen bonding from either N-H group gives conformations that are very similar in energy. Single crystal XRD studies were used to characterize ligands 1 and 4 and the related complexes 1a and 4a. The structures reveal that these complexes are mononuclear in the solid state and that copper adopts a regular square planar geometry. In both metallic species, the N, N', N''-trisubstituted guanidine ligands chelate the Cu(II) atom using the oxygen and one nitrogen. The synthesized compounds were investigated for urease inhibition using thiourea as a standard drug. Most complexes exhibit a better activity than the respective guanidines and compound 1a was found to be the most active with IC(50) = 9.83 ± 0.07 μM (the IC(50) for thiourea is 21.0 ± 0.1 μM). The species were also screened for their anti-leishmanial activity. However, all of the compounds were devoid of any significant activity.

Synthesis and structural characterization of new bioactive ligands and their Bi(III) derivatives

“…Agar tube dilution protocol and agar well diffusion methods were used for the preliminary screening of precursors I a – I e and then compounds 1 – 5 against various strains of fungi and bacteria. Following published protocols, the synthesized compounds were also tested for their antioxidant, lipoxygenase, α‐glycosidase and anti‐urease activities.…”

Synthesis, Structural Characterization, and Evaluation of the Biological Properties of Heteroleptic Palladium(II) Complexes

“…The data were integrated using the programme SAINT [30] and were corrected for Lorentz and polarization effects. The structure was solved and refined using SHELXS-97 and SHELXL-97 [31]. All the non-H atoms were refined anisotropically.…”

Structurally Diversified Heterocycles and Related Privileged Scaffolds as Potential Urease Inhibitors: A Brief Overview

“…Murtaza et al 115 demonstrated the synthesis of a series of N , N ′, N ″‐trisubstituted guanidines and their copper(II) complexes. The synthesized compounds have been subjected to the urease inhibition screening.…”