A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Abstract

A simple method was employed for the synthesis of dihydropyrano [3, 2-b] chromenedione derivatives (4a-o) in high yields by condensation of 5, 5dimethylcyclohexane-1, 3-dione(1), different aromatic aldehydes (2a-o), and 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one(3), using meglumine as a stable and reusable catalyst. Meglumine, an amino sugar, was employed as an environmentally benign catalyst, due to its splendid properties such as being inexpensive, recyclable, and biodegradable. The accomplished protocol employs low catalyst loading and easy work-up for the synthesis of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one derivatives. A great asset is that without any significant loss, the catalyst could be recovered and reused for extended synthetic steps. This offer huge advantage to overcome recyclability issues. Our synthesized compounds were analyzed by IR, 1 H, 13 C NMR, mass spectra and evaluated for their antioxidant properties by 1, 1-diphenyl-2-picryl hydrazyl radical (DPPH), hydrogen peroxide(H 2 O 2 ), and nitric oxide (NO) scavenging methods. The correlation in exhibition of antioxidant activity was effective at all doses. The binding interactions and molecular docking studies for entitled compounds were studied against 3MNG protein; 4k exhibited marked binding affinity with excellent docking score of −7.6 Kcal/mol and emerged as a lead compound.

Enforced Electronic‐Donor‐Acceptor Complex Formation in Water for Photochemical Cross‐Coupling

“…[41] In addition to its low cost, high solubility in water, low toxicity, non-corrosiveness, biocompatibility and biodegradability, [40,41] it is used in organic synthesis as hydrogen bond or electron donor. [40][41][42][43][44][45][46] In particular, meglumine has been shown to significantly improve the solubility and stability of poorly water-soluble compounds in water. [40,[42][43][44][45]47] The formation of light-absorbing enforced EDA complexes from aryl halides and indoles, anilines, anisoles, or thiols has been observed, when dissolved in water.…”

“…Meglumine is a sugar alcohol containing five hydroxyl groups and one secondary amino group, derived from sorbitol [40, 41] . The compound is an FDA‐approved pharmaceutical excipient [41] .…”

Electrochemical oxidation of meglumine in a pharmaceutical formulation using a nanocomposite anode

“…It can be applied either as a counterion to form a salt with active pharmaceutical ingredients (APIs) or as a functional excipient in the pharmaceutical industry and in clinical analysis, since it has low toxicity alongside high biocompatibility and biodegradability [1,2]. Moreover, it can act as catalyst in multicomponent reactions [3,4]. As a counterion, it is typically employed to formulate pharmaceutical contrast agents.…”

“…In the commercial pharmaceutical formulation of Gd-DOTA (branded drug DOTAREM ® ), meglumine is the counterion of (Gd) 4,7,4,7, and favors its solubility. It is often administered to patients for MRI to enhance tissue contrasts.…”

Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials

“…It possesses astonishing physical and chemical properties such as biocompatibility, biodegradability, stability to air and moisture, and water miscibility. Also, it is inexpensive and readily available in the market. − …”