Study on one-pot four-component synthesis of 9-aryl-hexahydro-acridine-1,8-diones using SiO2–I as a new heterogeneous catalyst and their anticancer activity

Abstract

a b s t r a c tA simple, efficient and cost-effective method for the synthesis of 9-aryl-hexahydro-acridine-1,8-diones by a one-pot four-component cyclocondensation of dimedone, aromatic aldehydes and ammonium acetate as a nitrogen source in the presence of a new heterogeneous catalyst silica iodide (SiO 2 -I) in EtOH at 80°C is described. SiO 2 -I was subjected to SEM-EDX and found to have iodo group bound to the catalyst. Some of the prepared acridine-diones were found to exhibit promising anti-cancer activity against HepG2 and MCF-7 cell lines.

Microwave-promoted three-component Hantzsch synthesis of acridinediones under green conditions

“…20,21 Because of the great conveniences of acridinediones, therefore, the immense interest has been devoted to the synthesis of these materials using heterogeneous or homogeneous catalyst systems. [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] Although most of the reported methods exhibit the useful synthetic advantages, however they generally suffer from shortcomings in terms of using expensive and hazardous solvents/reagents, the prolonged reaction times, undesirable yields, harsh reaction conditions and tedious work-up procedures. Therefore, the development and introduction of a green and practical approach which eliminate utilizing cost-effective solvents/catalysts from the medium of reactions, based on the principles of green chemistry, is more demanded.…”

Copper-catalyzed Ullmann reaction for the synthesis of fused hexacyclic heterocycles containing naphthyridine, acridine, and pyrazole (imidazole) moieties

“…1), which is an effective antimicrobial agent to inhibit gram-negative bacteria [5,6]. Acridine is another fused tricyclic heterocycle containing one nitrogen atom, which is also a ubiquitous heterocycle for anticancer activity in its derivatives [7][8][9][10][11][12]. A worth-to-be-noted drug is amsacrine (Fig.…”

An Efficient One-Pot Four-Component Synthesis of 9-Aryl-Hexahydroacridine-1,8-Dione Derivatives in the Presence of a Molecular Sieves Supported Iron Catalyst

“…Acridinediones are a highly important class of organic compounds, since they possess a wide range of pharmaceutical and biological activities such as a positive ionotropic effect promoting the entry of calcium to the intracellular space [2], anticancer activity [3], enzyme and tumour cell inhibition [4], antimicrobial activity and cytotoxicity [5]. They have structural similarity to 1,4-dihydropyridines (1,, which are well known intermediates in the synthesis of several pharmaceuticals including those for the treatment of hypertension and cardiovascular diseases [6].…”