Ionic Sal-SG Schiff bases as new synergetic chemotherapeutic candidates: synthesis, metalation with Pd(ii) and in vitro pharmacological evaluation

Abstract

8 A series of novel N-(salicylidene)-sulfaguanidines (Sal-SG) bearing ionic liquids (ILs) 9 terminals (ILSSGH, 4a-f) have been synthesized by Schiff base condensation of ILs-10 functionalized salicylaldehydes (ILSal, 3a-g) and sulfaguanidine (SG). Metalation trials of 11 these ionic Schiff bases with palladium(II) chloride affords the corresponding Pd(II) 12 complexes, [Pd(II)(ILSSG)Cl(H 2 O)] (5a-g). Further, the antimicrobial profiles of new 13 compounds against a set of common pathogens have been described. Zone of inhibitions 14 (ZOIs) and minimal inhibitory concentration (MIC) values revealed that most of the new 15 compounds exhibited significant antibacterial and potential inhibitory activity against 16Staphylococcus aureus (S. aureus), and this activity is modulated by substituents attached to 17 the ionic liquid core as well as the counter-ion. 18

Salicylaldehydes Derived from 5-Chloromethyl-2-hydroxybenzaldehyde – Synthesis and Reactions

“…29 Despite being widely used, the Blanc reaction of salicylaldehyde is known to have a series of shortcomings such as poor reproducibility or broad range of reported yields, which could stem from the co-existence in the final reaction mixture of the target product, of the intermediate carbinol and various side products which could potentially convert into one another under the employed reaction condition, 25 and even from the presence of 3-chloromethylsalicylaldehyde as a by-product of chloromethylation. 30 From an experimental point of view, chloromethylation of salicylaldehyde has been usually performed with formalin, in concentrated aqueous HCl as reaction medium, at room temperature, with reaction times extending up to 48 h. Occasionally, the use of zinc chloride 31 or sulfuric acid 32 as catalysts has been reported. The synthetic procedure employed in this study for the preparation of the starting material was adapted from a published procedure, 33 in which formalin was substituted by paraformaldehyde, owing to the latter's ability to depolymerize under acidic conditions (Scheme 1).…”

Ionic liquids for the preparation of biopolymer materials for drug/gene delivery: a review

“…Moreover, the combination of biologically relevant compounds can improve the biocompatibility of the systems. Imidazolium or pyridinium-based ILs demonstrate significantly higher antimicrobial and antitumor activities than other ILs, 235,236 which can be exploited as antimicrobial and antitumor substances in the pharmaceutic industry. As a result, early efforts have been dedicated to developing these antimicrobial and anticancer biopolymeric ILs.…”

Acyclic and cyclic imines and their metal complexes: recent progress in biomaterials and corrosion applications

“…The current literature search has highlighted antibacterial resistance in community pathogens as a major problem, and to overcome this a new generation of antibiotics should be revived. 47,48 For instance, Shanty et al have prepared Schiff bases (H 1 -H 7 ) (Scheme 9). These compounds were screened for enzyme inhibition, antibacterial, cytotoxic and in vivo antidiabetic activities and compounds were found to be active against one or other activity.…”