Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles

Abstract

Some of the hybrid compounds exhibited promising trypanocidal and anticancer activities.

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

“…However, compounds 9 and 10 are single diastereomers, the relative stereochemistry is trans . The trans -stereochemistry was confirmed by comparison with previously reported data [41,47a]. …”

“…Recently, we reported the synthesis of a new class of naphthoquinone compounds, containing a pendant 1,2,3-triazole motif from C-allyl lawsone ( 23 ) [47]. The iodination of 23 affords compounds 24 and 27 in 68% yield and 1:1 ratio (Scheme 5), which were easily separated by column chromatography.…”

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

“…A diverse set of 1,5-triazole products can be found in these reports which cover a wide range of targets and target classes including various enzyme inhibitors, [203][204][205][206][207][208][209][210][211][212][213] kinases, [214][215][216][217] proteases, 110,112 antivirals 218 (see also chapter 5.3) G-protein coupled receptors (GPCRs), 219 ion channels, [220][221][222] heat shock proteins, 95 and tRNA ligands. 223 1,5-Triazole derivatives have shown activity against numerous cancer cell lines, 205,215,[224][225][226][227] and against the parasites Trypanosoma cruzi 70,228 and Plasmodium falciparum. 205 They have also been employed in the search for new antimicrobiotics 229 and antifungal agents.…”

On the synthesis of quinone-based BODIPY hybrids: New insights on antitumor activity and mechanism of action in cancer cells

“…The synthesis of the quinone-based BODIPY hybrids 8-11 was accomplished by a convergent synthetic route, 24 using a classical copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. 27 We used an alkyne-containing BODIPY and azidecontaining quinones to assemble fluorescent, hybrid quinoidal-BODIPY molecules.…”

“…23 Recently, our group has described the first fluorescent lapachone-BODIPY hybrid as well as biological studies, including cytotoxic activity in different cancer cell lines and cell imaging experiments (Scheme 1B). 24 Herein, we have developed a new chemical platform to prepare new lapachone derivatives coupled to the fluorescent BODIPY core, which has excellent photophysical properties. 24b Lapachones exhibit potent antitumor activity due to their ability to act on multiple targets, as we have recently demonstrated.…”