Synthesis, characterisation, biological evaluation andin silicostudies of sulphonamide Schiff bases

Abstract

Sulphonamides are biologically important compounds with low toxicity, many bioactivities and cost-effectiveness. Eight sulphonamide derivatives were synthesised and characterised by FT-IR, 13 C NMR, 1 H NMR, LC-MS and elemental analysis. Their inhibitory effect on AChE, and carbonic anhydrase I and II enzyme activities was investigated. Their antioxidant activity was determined using different bioanalytical assays such as radical scavenging tests with ABTS þ , and DPPH þ as well as metal-reducing abilities with CUPRAC, and FRAP assays. All compounds showed satisfactory enzyme inhibitory potency in nanomolar concentrations against AChE and CA isoforms with K I values ranging from 10.14 ± 0.03 to 100.58 ± 1.90 nM. Amine group containing derivatives showed high metal reduction activity and about 70% ABTS radical scavenging activity. Due to their antioxidant activity and AChE inhibition, these novel compounds may be considered as leads for investigations in neurodegenerative diseases.

Synthesis, Characterization, and Inhibition Study of Novel Substituted Phenylureido Sulfaguanidine Derivatives as α‐Glycosidase and Cholinesterase Inhibitors

“…All compounds against of α‐glycosidase enzyme demonstrated efficient inhibition profiles with IC 50 values in the range of 11.72–46.11 nM, and K I values in the range of 14.44±0.88–43.53±9.06 nM [37] . In another study, a series of sulfonamide Schiff bases ( 1 – 4 ) and their reduced counterparts ( 5 – 8 ) were tested against AChE, and the compounds against AChE demonstrated efficient inhibition profiles with K I values in the range of 20.98±0.89 to 77.02±9.34 nM for AChE [38] . Lolak et al [39] .…”

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives

“…[30] In another study, a series of sulfonamide Schiff bases and their reduced counterparts were synthesized and assessed against hCA I, II isoforms, and AChE, and the K I values were found to be in the range of 16.05 ± 0.47-29.66 ± 0.50 nM for hCA I and II and 20.98 ± 0.89-77.02 ± 9.34 nM for AChE. [31] In a previous study, a series of aromatic and heterocyclic bis-sulfonamide Schiff bases against hCA I, II, VII, and IX was investigated, and many of the compounds showed a low nanomolar potency against hCA II, with K I values in the range of 0.4-861.1 nM. [32] In the present study, a series of novel, structurally diverse ST1-11 was synthesized as a modified procedure presented in our previous studies [3,25,26] and outlined in Scheme 1.…”

Novel benzoic acid derivatives: Synthesis and biological evaluation as multitarget acetylcholinesterase and carbonic anhydrase inhibitors

“…The three‐dimensional (3D) crystal structures of ligand‐bound HI6 (PDB ID: 5HF9 for AChE), [ 76 ] GZH (PDB ID: 6I0L for hCA I), [ 77 ] and GTQ (PDB ID: 4E3D for hCA II) [ 46 ] were retrieved from the Protein Data Bank [ 78 ] and were prepared utilizing the Protein Preparation Wizard. [ 79 ] The 3D structures of novel synthesized methylene‐aminobenzoic acid and tetrahydroisoquinolynyl‐benzoic acid derivatives ( 4a – g and 6a – g ) were sketched by ChemDraw [ 80 ] version 19.0 for Mac (PerkinElmer Inc.). They were suitably optimized for their ionization states at pH 7.4 ± 0.5 [ 81 ] with Epik [ 82 ] in the OPLS3e force field [ 83 ] using the LigPrep module [ 84 ] with default settings.…”