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- W2987201478 abstract "New furan and thiophene derivatives of aldimines o-HO-C6H4NCHC4H4X(R) (X = O, S; R = H, SiMe3, SiEt3, GeMe3, GeEt3) were synthesized by condensation of o-aminophenol with the substituted aldehyde precursor. Their structure, electrochemical reduction/oxidation (in CH3CN/0.1 M Bu4NPF6), frontier orbital energies, and cytotoxicity have been studied. Their electrochemical redox potentials Ep show good correlation with the corresponding orbital energies and the difference Epox – Epred corresponds well to their orbital hardness. These new compounds have a pronounced cytotoxicity toward cancer cells of human fibrosarcoma HT-1080 and mouse hepatoma MG-22A (IC50 ≅ 1–8 μg ml−1) that can be modulated by introducing a Me3M substituent into the fifth position of the heterocycle (e.g., IC50(Me3Si)/IC50(H) ≥ 50). R3M-substitution reduces the orbital hardness of the aldimines studied and facilitates oxidation, promoting their oxidative metabolism. The neighboring group effect in the α-Me3Si-substituted thiophene derivative favors S-oxidation, which supposedly makes its metabolic mechanism different compared to R3M-substituted furan series (or for M = Ge in the thiophene series). Interestingly, SiMe3 and GeMe3 groups in both heterocyclic series (furan and thiophene) cause opposite trends in cytotoxicity, while the silyl group increases it, the germyl group decreases it. De nouvelles aldimines o-HO-C6H4NCHC4H4X(R) (X = O, S; R = H, SiMe3, SiEt3, GeMe3, GeEt3), dérivées du furanne et du thiophène, ont été synthétisées par la condensation d'o-aminophenol avec l'aldéhyde précurseur substitué correspondant. La structure, la réduction et l'oxydation électrochimique (dans CH3CN/0.1 M Bu4NPF6), les énergies des orbitales frontières et la cytotoxicité de ces composés ont été étudiées. Les potentiels redox électrochimiques Ep de ces composés montrent une bonne corrélation avec les énergies orbitalaires correspondantes, et la différence Epox – Epred correspond bien à leur dureté orbitalaire. Ces nouveaux composés ont une cytotoxicité prononcée sur les cellules du fibrosarcome humain HT-1080 et de l'hépatome de souris MG-22A (IC50 ≅ 1–8 μg ml−1); elle peut être modulée par l'introduction d'un substituant Me3M en position 5 de l'hétérocycle (par exemple, IC50(Me3Si)/IC50(H) ≥ 50). Cette substitution réduit la dureté orbitalaire des aldimines étudiées et facilite leur oxydation en favorisant le métabolisme oxydatif. L'effet d'un groupe voisin dans le thiophène substitué en position α par Me3Si favorise son S-oxydation, ce qui vraisemblablement rend son mécanisme métabolique différent par rapport à celui des dérivés R3M-substitués dans la série du furanne (ou pour M = Ge dans la série du thiophène). Il est intéressant de noter que les groupements SiMe3 et GeMe3 dans les deux séries hétérocycliques (furanne, thiophène) ont des effets opposés sur la cytotoxicité: le groupement silyle l'augmente, tandis que le groupement germyle la réduit." @default.
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- W2987201478 date "2019-09-01" @default.
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- W2987201478 title "Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity" @default.
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