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A novel, one-pot, three-component coupling (3-CCR) reaction of aromatic aldehydes, β-naphthol, and 6-amino-1,3-dimethyl uracil in a deep eutectic solvent (DES) has been developed as a highly efficient and selective method for the expedient synthesis of the densely functionalized 8,10-dimethyl-12-phenyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione framework in synthetically pleasing yield. The devised protocol adeptly harnesses the versatility of DESs, resulting in a straightforward, cost-effective, resilient, and environmentally sustainable synthetic approach. The resulting cascade adduct exhibits noteworthy antiproliferative activity against a variety of cancer cell lines, thereby showing promise as a potential anticancer drug candidate for breast and hepatocellular carcinoma with moderate to good IC50 values. The most potent compounds in the synthesized library, 4m and 4l, exhibit highly potent cytotoxicity against HepG2 and MCF7 cancer cell lines, with notable IC50 values of 46.39 and 28.21 μM, respectively. The present findings are corroborated by computational and molecular docking studies. The density functional theory (DFT) calculations underscore the pivotal role of the naphthyl ring in orchestrating the success of this intricate domino process in delivering the anticipated scaffolds in reasonable yields. [ABSTRACT FROM AUTHOR]

Organocatalysis is the use of non-stoichiometric amounts of low-molecular-weight organic molecules made up of C, H, N, O, S, and P to accelerate stereoselective chemical transformations. Despite having a long history, the use of small organic molecules as chiral catalysts in enantioselective synthesis has only recently intrigued scientists interest. However, in synthetic and medicinal chemistry, there has been a resurgence of interest in performing asymmetric synthesis of a variety of important targets by utilizing an organocatalytic approach as a leading reaction. The development of an asymmetric protocol for the synthesis of enantioenriched molecules of therapeutic relevance is crucial in the development of new drug candidates. Modern asymmetric catalysis is based on three pillars: (i) biocatalysts (i.e., enzymes), (ii) transition metal catalysis, and (iii) organocatalysis. Among these catalytic systems, organocatalysis has become the most flourishing field within the field of a catalytic regime that offers many significant benefits to synthetic and medicinal chemists. In contrast to many metal-based catalytic models, most organocatalysts have a high tolerance capability for air and moisture, easy availability, easy handling, non-toxic and enantiomeric purity, etc. They are often derived from natural resources of high enantiomeric virtue with the desired stereocentre or easily synthesized in the laboratory in some simple synthetic operations. This perspective aims to draw readers' attention to the power of asymmetric organocatalysis in assembling glycosyl donors and acceptors in the synthesis of biologically significant stereodefined O-glycosides. Glycosylation is a fundamental chemical transformation and is ubiquitous in both nature and chemical laboratories. In nature, the glycosylation processes are carried out by enzyme catalysis. We were interested in portraying the recent impressive progress achieved by the scientific community in the field of chemical glycosylation, specifically O-glycosylation. Poly-functionalized sugar moieties offer many opportunities to discover new drug candidates in which the modification of aglycone through the glycosylation process is a key reaction. [ABSTRACT FROM AUTHOR]