Natural dihydroisobenzofuran derivatives as a template for promising radical scavengers: theoretical insights into structure–activity relationships, thermochemistry and kinetics

Abstract

Dihydroisobenzofuran heterocycle is a structural motif found in a number of medications with anti-tumour, anti-diabetic, and antibacterial activities. It is also found in a slew of natural substances, most notably fungus metabolites, which have been shown to possess credible radical scavenging activity. Density functional theory studies on three different derivatives were conducted to investigate their electronic structures as well as thermochemical and kinetic behaviour against ·OOH, ·OH, and ·OCH3 in biologically relevant solvents, with the goal of elucidating structure–activity relationships and discussing the potential role of the scaffolds as a template for new semisynthetic antioxidants. The importance of resonance and inductive effects, and also hydrogen bonding, has been underlined, but most importantly, it has been demonstrated that all structures have considerable scavenging potential against all studied radicals, with reactions rates close to the diffusion limit.

Unveiling the Antioxidative Potential of Galangin: Complete and Detailed Mechanistic Insights through Density Functional Theory Studies

“…Similar to the previous antioxidative activities, the OIL-1 type properties were explored for forms with non-negligible populations (the molar fraction greater than 0.1%), consistent with previous papers − .. Gibbs free energies of reaction and reaction rates for the reduction of the complexes with O 2 •– and Asc – , along with the same reaction for the reference Cu(H 2 O) 4 2+ are given in Table .…”

N-, O- and S-Heterocycles Synthesis in Deep Eutectic Solvents

“…Furthermore, this one-pot tandem methodology was also active when an electron-poor unsaturated substrate 82 (i.e., maleic anhydride and N-methylmaleimide) was employed for the synthesis of exo-regioisomers 7-oxanorbornanes 84 (Scheme 27b) in a selective manner. Regarding the class of five-membered O-containing heterocycles, dihydroisobenzofuranes are a very widespread molecular structure in a plethora of natural substances [74]. Furthermore, the heterocyclic 1,3-diyhdroisobenzofurane functionality has been demonstrated to have among the most disparate therapeutic activities [75][76][77].…”

“…The process was carried out for 8 h at 50 °C in the presence of a PdI2/KI catalytic system, leading to the desired heterocycles 90 in 65-83% yields (Scheme 29a). For all the examples reported, the DES/catalytic system could be Regarding the class of five-membered O-containing heterocycles, dihydroisobenzofuranes are a very widespread molecular structure in a plethora of natural substances [74]. Furthermore, the heterocyclic 1,3-diyhdroisobenzofurane functionality has been demonstrated to have among the most disparate therapeutic activities [75][76][77].…”

“…Regarding the class of five-membered O-containing heterocycles, dihydroisobenzofuranes are a very widespread molecular structure in a plethora of natural substances [74]. Furthermore, the heterocyclic 1,3-diyhdroisobenzofurane functionality has been demonstrated to have among the most disparate therapeutic activities [75][76][77].…”