Design, synthesis and mechanism study of novel natural-derived isoquinoline derivatives as antifungal agents

Design, synthesis, and mechanism study of novel 1-arylisoquinoline derivatives as antifungal agents

“…2-(3′,4′-dimethoxypheny1)ethy1amine 1 reacts with appropriate aldehydes 2a-2h in anhydrous toluene to form the intermediate diazo compound 3a-3h. The intermediate 1-substituted-6,7-dimethoxy-1,2,3,4tetrahydroisoquinoline compound 4a-4h is obtained by intramolecular cyclization with tri uoroacetic acid [22]. Compound 4a-4h was condensed with Boc-glycine to obtain intermediate 5a-5h.…”

Various Biomimetics, Including Peptides as Antifungals

“…To inhibit the enzymatic activity of fungi, synthetic substrates acting as mimetics or specific inhibitors can be used to reduce the metabolic activity of fungi or to carry out their catalytic or physiological functions, reducing the biosynthesis of a number of metabolites and preventing their growth (Table 4) [16,[95][96][97][98][99][100][101][102]. Biomimetic substrates should, on the one hand, inhibit the widest possible range of fungal enzymes and, on the other hand, not be inhibitors for enzymes of plant and animal origins.…”

“…Succinate dehydrogenase provides electrons for aerobic respiratory circuits in the mitochondria of eukaryotic fungal cells. New 3-aryl-isoquinoline derivatives (#63), based on sanguinarine (heleritrine and berberine) inhibiting this enzyme, have been synthesized [100]. The fungicidal activity of the compounds (#63) obtained at a concentration of 50 mg/L was higher in comparison with the antimicrobial action of sanguinarine, which inhibits mycelial growth of Alternaria solani, A. alternata and Physalospora piricola.…”

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

“…Chen et al reported a four-step synthesis of 3-aryl-isoquinolium derivative 403 (Scheme 80). 126 The reaction sequence initiates by treating 2-chloro-5-iodopyridine 396 with mesitylene 397 mediated by m CPBA to generate the aryl iodonium triflate adduct 398 . [4 + 2] cycloaddition of intermediate 398 with furan 399 furnishes the bicyclic adduct 400 that on further treatment with BBr 3 following the methylation affords 401 , which on Suzuki coupling provides isoquinoline 402 .…”

“…Chen et al reported a four-step synthesis of 3-aryl-isoquinolium derivative 403 (Scheme 80). 126 The reaction sequence initiates by treating 2-chloro-5-iodopyridine 396 with Subsequent acidic treatment of isoquinoline 402 under inert conditions affords 3-aryl-isoquinoline derivative 403. The synthesised 3-aryl-isoquinoline derivatives have been inspected for antifungal properties, where they exhibit broad spectrum and excellent fungicidal activities, mainly the isoquinoline ring system with naphthyl tethering at the C-4 atom exhibits the most robust effectiveness against A. solani (80.4%), A. alternata (88.2%), and P. piricola (93.8%), respectively.…”