1. Design and synthesis of novel potent anticoagulant and anti-tyrosinase pyranopyrimidines and pyranotriazolopyrimidines: Insights from molecular docking and SAR analysis
- Author
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Hichem Ben Jannet, Sarra Chortani, Vijaykumar D. Nimbarte, Meriem Debbabi, Samia Chekir, Anis Romdhane, Université de Monastir - University of Monastir (UM), Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), and Normandie Université (NU)-Normandie Université (NU)
- Subjects
Agaricus ,Pyranotriazolopyrimidines ,Anti-tyrosinase ,01 natural sciences ,Biochemistry ,Structure-Activity Relationship ,Anti tyrosinase ,Drug Discovery ,Humans ,[CHIM]Chemical Sciences ,Enzyme Inhibitors ,Molecular Biology ,Pyrans ,Binding Sites ,Primary (chemistry) ,Molecular Structure ,Monophenol Monooxygenase ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Anticoagulant ,Molecular Docking Analysis ,Anticoagulants ,Triazoles ,Carbon-13 NMR ,Combinatorial chemistry ,0104 chemical sciences ,Molecular Docking Simulation ,Pyranopyrimidines ,010404 medicinal & biomolecular chemistry ,Pyrimidines ,Molecular docking ,Proton NMR ,Partial Thromboplastin Time ,SAR - Abstract
International audience; 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
- Published
- 2019