Design and synthesis of novel potent anticoagulant and anti-tyrosinase pyranopyrimidines and pyranotriazolopyrimidines Insights from molecular docking and SAR analysis

Meriem Debbabi (1) , Vijaykumar D. Nimbarte (2) , Samia Chekir (1) , Sarra Chortani (1) , Anis Romdhane (1) , Hichem Ben Jannet (1)

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

Pyrimidine-fused compounds are of great interest for the discovery of potent bioactive agents. This study describes the synthesis of novel pyranopyrimidines 3a-f and pyranotriazolopyrimidines 4a-d derivatives via the cyclocondensation reaction of α-functionalized iminoether 2, which was obtained from 2-amino-3-cyanopyrane 1, with a series of primary aromatic amines and hydrazides, respectively. Structures of all synthesized compounds were established on the basis of spectroscopic methods including 1H NMR, 13C NMR and ES-HRMS. They were finally tested for their anticoagulant and anti-tyrosinase activities. Significant results have been obtained and the structure-activity relationship (SAR) was discussed with the help of molecular docking analysis. © 2018

Keywords: Anti-tyrosinase; Anticoagulant; Molecular docking; Pyranopyrimidines; Pyranotriazolopyrimidines; SAR

Domains: Chemical Sciences

Meriem Debbabi, Vijaykumar D. Nimbarte, Samia Chekir, Sarra Chortani, Anis Romdhane, et al.. Design and synthesis of novel potent anticoagulant and anti-tyrosinase pyranopyrimidines and pyranotriazolopyrimidines Insights from molecular docking and SAR analysis. Bioorganic Chemistry, 2019, 82, pp.129-138. ⟨10.1016/j.bioorg.2018.10.004⟩. ⟨hal-02413307⟩