Pharmaceutically relevant (hetero)cyclic compounds and natural products from lignin-derived monomers: Present and perspectives

Abstract

Summary Lignin, the richest source of renewable aromatics on the planet, is an intriguing raw material for the construction of value-added aromatics. In the past decade, much progress has been made regarding the development of efficient lignin depolymerization methods, able to produce specific monophenol derivatives in high-enough selectivity and yields. This now serves as an excellent basis for developing powerful downstream conversion strategies toward a wide range of products, including fine chemical building blocks. The inherent structural features of lignin-derived platform chemicals undoubtedly inspire the development of novel, creative, atom-economic synthetic routes toward biologically active molecules or natural products. In this perspective we attempt to bridge the structural features of lignin-derived platform chemicals with existing synthetic strategies toward the construction of heterocycles and provide a summary of efforts for the production of natural products from aromatics that can be, in principle, obtained from lignin. Last, we comment on the latest efforts that present entire value-chains from wood to valuable pharmaceutically relevant compounds.

Taming the radical cation intermediate enabled one-step access to structurally diverse lignans

“…We report in this paper a unified strategy to access diverse subclasses of lignans from biomass-derived monolignols 68 . Under photoredox catalytic conditions, C-7 functionalized aryltetralin cyclic ethers, dibenzyl tetrahydrofurans with different oxidation levels at benzylic positions are readily prepared in one operation by varying the stoichiometry of nucleophiles and additives (oxidant or hydrogen donor).…”

Schizandrin A can inhibit non‑small cell lung cancer cell proliferation by inducing cell cycle arrest, apoptosis and autophagy

“…Vinblastine (13), platinum compounds (14) and paclitaxel (15) are all examples of anti-cancer agents that can be found naturally. In addition, monomer compounds purified from natural products also form part of the drug screening libraries (16)(17)(18). Their biological activities on various processes, including inflammation, infection and cancer development, have been extensively investigated (19).…”

Design and Synthesis of Benzoxepine–Based 1,2,3‐Triazoles: Molecular Docking and in vitro Antimicrobial Activity Evaluation

“…[18] On the other hand, Benzoxazepines represent a key motif in heterocyclic chemistry and occupy an important place in medicinal chemistry, nucleic acids, hormones and therapeutic drugs. [19] These derivatives are well-known pharmacophores showing capable properties against various diseases such as central nervous system damage, [20] antipsychotic, [21] anti-HIV, [22] tranquilizing, [23] and anticancer activities. [24] Molecular docking analysis has been one of the most basic and important strategy for drug discovery and it allows prediction of molecular interactions between a ligand in the bound state and a protein at the atomic level, which allows to characterize the behavior of small molecules in the binding site of target proteins as well as to elucidate fundamental biochemical processes.…”

“…On the other hand, Benzoxazepines represent a key motif in heterocyclic chemistry and occupy an important place in medicinal chemistry, nucleic acids, hormones and therapeutic drugs [19] . These derivatives are well‐known pharmacophores showing capable properties against various diseases such as central nervous system damage, [20] antipsychotic, [21] anti‐HIV, [22] tranquilizing, [23] and anticancer activities [24] …”