Aromatic Bio‐Based Solvents

Mubofu, Egid B.; Mgaya, James E.; Munissi, Joan J. E.

doi:10.1002/9781119065357.ch2

Cited by 1 publication

(1 citation statement)

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“…Next, we set out to construct variously substituted tetrahydroisoquinolines , via Pictet–Spengler cyclization involving the aminoalkyl guaiacols obtained above, by exploring the use of DESs for the first time in this transformation [22,32] . Due to their favorable physicochemical properties (low vapor pressure, potentially non‐toxic, biodegradable, and renewable nature), DESs are considered promising green alternatives for volatile organic solvents [33,34] . We reasoned that this unique class of alternative reaction media will actively facilitate imine formation and accelerate the subsequent Mannich‐type cyclization, both steps involved in the Pictet–Spengler mechanism [35] .…”

Section: Resultsmentioning

confidence: 99%

Clean Synthetic Strategies to Biologically Active Molecules from Lignin: A Green Path to Drug Discovery**

Afanasenko,

Wu,

De Santi

et al. 2023

Angewandte Chemie

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Deriving active pharmaceutical agents from renewable resources is crucial to increase the economic feasibility of modern biorefineries and promises to alleviate critical supply‐chain dependencies in pharma manufacturing. At the fundamental level, embracing the structural complexity of renewable resources offers hitherto unexploited opportunities for the green synthesis of essential pharmaceuticals, and opens new avenues in drug discovery. In this vein, our multidisciplinary approach combines research in lignin‐first biorefining, sustainable catalysis, and alternative solvents with bioactivity screening, an in vivo efficacy study, and a structural similarity search. The resulting sustainable path to novel anti‐infective, anti‐inflammatory, and anti‐cancer molecules enabled the rapid identification of frontrunners for key therapeutic indications. Most significantly, we discovered an anti‐infective against the priority pathogen Streptococcus pneumoniae, showing efficacy in vivo and promising plasma‐ and metabolic stability. Our established chemocatalytic methods, inspired by the innate structural features of lignin, provide straightforward access to synthetically challenging biologically active molecules of the core dopamine structure, namely tetrahydroisoquinolines, quinazolinones, 3‐arylindoles and the natural product tetrahydropapaveroline. Our diverse array of atom‐economic transformations produce only harmless side‐products and use benign reaction media, such as tunable deep eutectic solvents for modulating reactivity in challenging cyclization steps.

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Section: Resultsmentioning

confidence: 99%