2. Academic Validation
  3. Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities

Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities

  • Bioorg Med Chem Lett. 2016 May 15;26(10):2450-2454. doi: 10.1016/j.bmcl.2016.03.108.
Marwa Gardelly 1,  Belsem Trimech 1,  Mohamed Amine Belkacem 2,  Mounira Harbach 3,  Soukaina Abdelwahed 4,  Amor Mosbah 5,  Jalloul Bouajila 6,  Hichem Ben Jannet 7
Affiliations

Affiliations

  • 1 Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11SE39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia.
  • 2 Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11SE39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia; University of Toulouse, Faculty of pharmacy of Toulouse, Laboratory of Molecular Interactions and Chemical and Photochemical reactivities, UMR CNRS 5623, University Paul-Sabatier, 118 Narbonne Road, F-31062 Toulouse, France.
  • 3 Laboratory of Bioressources: Integrative Biology and Valorization, Higher Institute of Biotechnology of Monastir, University of Monastir, Avenue of Tahar Haddad, 5019 Monastir, Tunisia.
  • 4 LR Biotechnology and Bio-Geo Resources Valorization (LR11ES31), Higher Institute of Biotechnology-University of Manouba, Biotechpole of Sidi Thabet, 2020 Sidi Thabet, Ariana, Tunisia.
  • 5 Laboratory of Bioressources: Integrative Biology and Valorization, Higher Institute of Biotechnology of Monastir, University of Monastir, Avenue of Tahar Haddad, 5019 Monastir, Tunisia; LR Biotechnology and Bio-Geo Resources Valorization (LR11ES31), Higher Institute of Biotechnology-University of Manouba, Biotechpole of Sidi Thabet, 2020 Sidi Thabet, Ariana, Tunisia.
  • 6 University of Toulouse, Faculty of pharmacy of Toulouse, Laboratory of Molecular Interactions and Chemical and Photochemical reactivities, UMR CNRS 5623, University Paul-Sabatier, 118 Narbonne Road, F-31062 Toulouse, France. Electronic address: jalloul.bouajila@univ-tlse3.fr.
  • 7 Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11SE39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia. Electronic address: hich.benjannet@yahoo.fr.
PMID: 27080182 DOI: 10.1016/j.bmcl.2016.03.108
Abstract

A series of α-aminocarbonitriles 2a-h, obtained by a condensation reaction of 4-hydroxycoumarin with malononitrile and a series of arylaldehydes, was reacted with Lawesson's reagent to give the diazaphosphinanes 3a-h and 3a'-h' as diastereoisomers. All the synthesized compounds were characterized by spectroscopic means such as NMR ((1)H, (13)C, (31)P) and MS. The synthesized compounds were evaluated for their cytotoxic activity in vitro against two tumor cell lines MCF-7 and HCT-116 and for their anti-tyrosinase effect. The results showed a moderate cytotoxic activity for most compounds and nearly all tested derivatives have been found considerable Tyrosinase inhibitors.

Keywords

Anti-tyrosinase activity; Coumarin; Cytotoxic activity; Diazaphosphinanes; Lawesson’s reagent.

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