title: Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities.
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.
authors.affiliation: 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.
authors.forename: Marwa
authors.initials: M
authors.lastname: Gardelly
authors.affiliation: 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.
authors.forename: Belsem
authors.initials: B
authors.lastname: Trimech
authors.affiliation: 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.
authors.forename: Mohamed Amine
authors.initials: MA
authors.lastname: Belkacem
authors.affiliation: Laboratory of Bioressources: Integrative Biology and Valorization, Higher Institute of Biotechnology of Monastir, University of Monastir, Avenue of Tahar Haddad, 5019 Monastir, Tunisia.
authors.forename: Mounira
authors.initials: M
authors.lastname: Harbach
authors.affiliation: LR Biotechnology and Bio-Geo Resources Valorization (LR11ES31), Higher Institute of Biotechnology-University of Manouba, Biotechpole of Sidi Thabet, 2020 Sidi Thabet, Ariana, Tunisia.
authors.forename: Soukaina
authors.initials: S
authors.lastname: Abdelwahed
authors.affiliation: 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.
authors.forename: Amor
authors.initials: A
authors.lastname: Mosbah
authors.affiliation: 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.
authors.forename: Jalloul
authors.initials: J
authors.lastname: Bouajila
authors.affiliation: 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.
authors.forename: Hichem
authors.initials: H
authors.lastname: Ben Jannet
mesh_terms: D015110:4-Hydroxycoumarins / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003979:Diazonium Compounds / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045325:HCT116 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010720:Phosphines / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D015110:4-Hydroxycoumarins; D000970:Antineoplastic Agents; D003374:Coumarins; D003979:Diazonium Compounds; D004791:Enzyme Inhibitors; D010720:Phosphines; D014442:Monophenol Monooxygenase; C044646:phosphine; C068805:4-hydroxycoumarin
keywords: Anti-tyrosinase activity; Coumarin; Cytotoxic activity; Diazaphosphinanes; Lawesson’s reagent