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Article Dans Une Revue Archiv der Pharmazie / Chemistry in Life Sciences Année : 2021

Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza‐analogs

Arnaud Pâris
  • Fonction : Auteur
El Mostafa Ketatni
Pierre Chalard
Mostafa Khouili
  • Fonction : Auteur
Richard Daniellou
Mohamed Akssira
  • Fonction : Auteur

Résumé

A concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lignans and aza-analogs was developed. The main objective was to develop synthetic tactics for the creation of the lactone and lactam unit that would give access to an array of synthetic, natural, and/or bioactive compounds through rather simple chemical manipulation. The flexibility and potentiality of these new processes were further illustrated by the total synthesis of retrojusticidin B (13b), justicidin C (14b), and methoxy-vitedoamine A (22a). In this study, a series of novel aryl-naphthalene lignans and aza-analogs were synthesized, and the cytotoxic activities of all compounds on cancer cell growth were evaluated. The target compounds were structurally characterized by 1H NMR (nuclear magnetic resonance), 13C NMR, infrared, high-resolution mass spectrometry, and X-ray crystallography. The IC50 values of these compounds on five tumor cell lines (A549, HS683, MCF-7, SK-MEL-28, and B16-F1) were obtained by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric assay. Five of the compounds exhibited excellent activity compared to 5-fluorouracil and etoposide against the five cell lines tested, with IC50 values ranging from 1 to 10 μM.
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Dates et versions

hal-03272496 , version 1 (28-06-2021)

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El‐mahdi Ourhzif, Arnaud Pâris, Isabelle Abrunhosa‐thomas, El Mostafa Ketatni, Pierre Chalard, et al.. Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza‐analogs. Archiv der Pharmazie / Chemistry in Life Sciences, 2021, 354 (6), pp.2000479. ⟨10.1002/ardp.202000479⟩. ⟨hal-03272496⟩
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