Synthesis, biological evaluation and molecular docking analysis of novel benzopyrimidinone derivatives as potential anti-tyrosinase agents

Sarra Chortani (1) , Vijaykumar D. Nimbarte (2) , Mabrouk Horchani (1) , Hichem Ben Jannet (1) , Anis Romdhane (1)

1 UM - Université de Monastir - University of Monastir
2 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

2-substitued-benzopyrimidinones 2 were synthesized in high to excellent yields in a single step via condensation of 2-aminobenzamide 1 with some aryl-aldehydes in the presence of iodine. Cyclocondensation reaction of hydrazides 3 which were obtained in two steps from benzopyrimidinones 2, with some electrophilic species such as 2,4-pentandione, 2,5-hexandione, 1-phenylbutan-1,3-dione and cyclic anyhdrides provided the new compounds 4a–c, 5a–c, 6a–c, 7a–c, 8a–c and 9a–c. The synthesized compounds were characterized by spectroscopic means. They were also evaluated for their anti-tyrosinase potential. The structure-activity relationship (SAR) was discussed on the basis of the molecular docking analysis. © 2019

Keywords: Anti-tyrosinase activity; Benzopyrimidinones; Cyclocondensation; Molecular docking; Pyrimidine hydrazides; SAR

Domains: Chemical Sciences

Sarra Chortani, Vijaykumar D. Nimbarte, Mabrouk Horchani, Hichem Ben Jannet, Anis Romdhane. Synthesis, biological evaluation and molecular docking analysis of novel benzopyrimidinone derivatives as potential anti-tyrosinase agents. Bioorganic Chemistry, 2019, 92, pp.103270. ⟨10.1016/j.bioorg.2019.103270⟩. ⟨hal-02413310⟩