Immunosuppressive effects of new thiophene-based KV1.3 inhibitors

Gubič, Špela; Montalbano, Alberto; Sala, Cesare; Becchetti, Andrea; Hendrickx, Louise Antonia; Theemsche, Kenny M. Van; Pinheiro-Júnior, Ernesto Lopes; Altadonna, Ginevra Chioccioli; Peigneur, Steve; Ilaš, Janez; Labro, Alain J.; Pardo, Luis A.; Tytgat, Jan; Tomašič, Tihomir; Arcangeli, Annarosa; Mašič, Lucíja Peterlin

doi:10.1016/j.ejmech.2023.115561

Cited by 1 publication

(2 citation statements)

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Section: Resultsmentioning

confidence: 99%

“…With the formation of the new prochiral carbon centre C-4, the two signals for protons H-4a and H-4b became non-equivalent. The occurrence of decarboxylation was further evidenced by a noticeable colour change from light yellow to dark green[30].Molecules 2024, 29, 2756 9 of 18 non-equivalent. The occurrence of decarboxylation was further evidenced by a noticeable colour change from light yellow to dark green [30].…”

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Spectral Assignment in the [3 + 2] Cycloadditions of Methyl (2E)-3-(Acridin-4-yl)-prop-2-enoate and 4-[(E)-2-Phenylethenyl]acridin with Unstable Nitrile N-Oxides

Maľučká,

Vilková

2024

Molecules

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The investigation of cycloaddition reactions involving acridine-based dipolarophiles revealed distinct regioselectivity patterns influenced mainly by the electronic factor. Specifically, the reactions of methyl-(2E)-3-(acridin-4-yl)-prop-2-enoate and 4-[(1E)-2-phenylethenyl]acridine with unstable benzonitrile N-oxides were studied. For methyl-(2E)-3-(acridin-4-yl)-prop-2-enoate, the formation of two regioisomers favoured the 5-(acridin-4-yl)-4,5-dihydro-1,2-oxazole-4-carboxylates, with remarkable exclusivity in the case of 4-methoxybenzonitrile oxide. Conversely, 4-[(1E)-2-phenylethenyl]acridine displayed reversed regioselectivity, favouring products 4-[3-(substituted phenyl)-5-phenyl-4,5-dihydro-1,2-oxazol-4-yl]acridine. Subsequent hydrolysis of isolated methyl 5-(acridin-4-yl)-3-phenyl-4,5-dihydro-1,2-oxazole-4-carboxylates resulted in the production of carboxylic acids, with nearly complete conversion. During NMR measurements of carboxylic acids in CDCl3, decarboxylation was observed, indicating the formation of a new prochiral carbon centre C-4, further confirmed by a noticeable colour change. Overall, this investigation provides valuable insights into regioselectivity in cycloaddition reactions and subsequent transformations, suggesting potential applications across diverse scientific domains.

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Section: Resultsmentioning

confidence: 99%

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confidence: 97%