Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities. Issue 10 (15th May 2016)

• Record Type: Journal Article
• Authors: Gardelly, Marwa; Trimech, Belsem; Belkacem, Mohamed Amine; Harbach, Mounira; Abdelwahed, Soukaina; Mosbah, Amor; Bouajila, Jalloul; Ben Jannet, Hichem
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 10(2016)
• Page Start: 2450
• Page End: 2454
• Publication Date: 2016-05-15
• Subjects: Diazaphosphinanes -- Coumarin -- Lawesson's reagent -- Cytotoxic activity -- Anti-tyrosinase activity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.03.108
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: A novel series of cytotoxic and anti-tyrosinase diazaphosphinanes3 has been synthesized by the treatment of previously prepared α-aminocarbonitriles2 accompanied by a Dimroth rearrangement. Abstract: A series of α-aminocarbonitriles2a –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 diazaphosphinanes3a –h and3a′ –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.