Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones – green palladium-catalysed Suzuki cross coupling

Abstract

Antifungal and trypanocidal aryl-1,4-naphthoquinones were prepared through an aqueous Suzuki protocol with reflux or microwave irradiation.

Synthetic Derivatives against Wild-Type and Non-Wild-Type Sporothrix brasiliensis: In Vitro and In Silico Analyses

“…The present study analyzed eleven new quinone derivatives against WT and NWT clinical isolates and the standard strain of S. brasiliensis. Quinone derivatives Q1 and Q8 exhibited MIC and MFC values compatible with potential antifungal molecules [28,29]. Indeed, Tandon et al [29,30], assessing quinone derivatives' antibacterial and antifungal potential, showed MICs between 6.25 and ≥50 µg/mL for distinct S. schenckii isolates.…”

“…Different authors have suggested that S. brasiliensis shows reduced sensitivity to azoles [12,14,23,25], underlining the need to distinguish therapeutic alternatives. Recently, quinones became the subject of several studies due to their diverse known biological activities, such as their antibacterial [26,27] and antifungal potential [21,28,29]. These drugs also have antifungal properties against S. schenckii [29].…”

Iron catalyzed C–C dehydrogenative coupling reaction: synthesis of arylquinones from quinones/hydroquinones

“…Examples include the transition-metal-catalyzed coupling of a stannylquinone with an arylhalide, 9 haloquinone with a styrylstannane 10 and halogenated quinones with boronic acids. 11 Heck type arylation often comprises unfunctionalized quinones and pre-functionalized arenes. Commercially available, but costly arylboronic acids were used in such transformations, in the presence of metal reagents made of such as Ag, Rh, Ir, Pd, and Fe salts.…”

A photochemical and theoretical study of the triplet reactivity of furano- and pyrano-1,4-naphthoquionones towards tyrosine and tryptophan derivatives

“…Many natural and synthetic naphthoquinones are known to possess varied and potent biological properties including trypanocidal, [1][2][3] antifungal, 4-8 leishmanicidal, [9][10][11][12] anti-inammatory, [13][14][15][16] and antitumor activities. [17][18][19][20][21][22] In this sense, quinones are important cytotoxic compounds and some examples have been clinically used for cancer chemotherapy, for example, anthracycline antibiotics and mitomycin-C. [23][24][25] In addition alapachone, a natural 1,4-naphthoquinone, and its derivatives present promising biological activity for example topoisomerase II-mediated DNA cleavage, 26,27 trypanocidal, 28,29 and antineoplastic activity.…”