Ferreira, Alana R.; Alves, Danielle da N.; de Castro, Ricardo D.; Perez-Castillo, Yunierkis; de Sousa, Damiao P. published an article in 2022. The article was titled 《Synthesis of Coumarin and Homoisoflavonoid Derivatives and Analogs: The Search for New Antifungal Agents》, and you may find the article in Pharmaceuticals.Reference of 2-Methoxybenzaldehyde The information in the text is summarized as follows:
A set of twenty-four synthetic derivatives, coumarin I [R = 4-OPr, 4-OiPr, 7-O-pentyl, etc.], II [R = Ph, 4-MeOC6H4, 4-MeC6H4, etc.; X = N, O] via alkylation and acylation reactions of com. coumarins, 4-hydroxycoumarin/7-hydroxycoumarin and homoisoflavonoid cores and its structural analogs III [R = H, 4-OMe, 3-OMe, etc.] via reactions between 4-chromanone and aldehydes catalyzed by pyrrolidine. The broth microdilution test was used to determine the Min. Inhibitory Concentration (MIC) of the compounds I, II and III and to verify the possible antifungal action mechanisms. The structures of the synthesized products I, II and III were characterized by FTIR spectroscopy: 1H-NMR, 13C-NMR, and HRMS. The coumarin derivative I [R = 7-O-pentyl, etc.] presented the best antifungal profile, suggesting that the pentyloxy substituent at the C-7 position of coumarin ring could potentiate the bioactivity. Compound I [R = 7-O-pentyl, etc.] was then evaluated against the biofilm of C. tropicalis ATCC 13803, which showed a statistically significant reduction in biofilm at concentrations of 0.268μmol/mL and 0.067μmol/mL, when compared to the growth control group. For a better understanding of their antifungal activity, compounds I [R = 7-O-pentyl, etc.] and III [R = H] were submitted to a study of the mode of action on the fungal cell wall and plasma membrane. It was observed that neither compound interacted directly with ergosterol present in the fungal plasma membrane or with the fungal cell wall which suggested that their bioactivity was due to interaction involving other pharmacol. targets. Compound I [R = 7-O-pentyl, etc.] was also subjected to a mol. modeling study, which showed that its antifungal action mechanism occurred mainly through interference in the redox balance of the fungal cell, and by compromising the plasma membrane; not by direct interaction, but by interference in ergosterol synthesis. Another important finding was the antifungal capacity of homoisoflavonoids III [R = 3-OMe, 2-OMe]. Derivative III [R = 3-OMe] presented slightly higher antifungal activity, possibly due to the presence of the methoxyl substituent in the meta position in ring B. In the experiment, the researchers used many compounds, for example, 2-Methoxybenzaldehyde(cas: 135-02-4Reference of 2-Methoxybenzaldehyde)
2-Methoxybenzaldehyde(cas: 135-02-4) is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. It also has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.Reference of 2-Methoxybenzaldehyde
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