AUTHOR=Godara Rajni , Kaushik Parshant , Tripathi Kailashpati , Kumar Rakesh , Rana Virendra Singh , Kumar Rajesh , Mandal Abhishek , Shanmugam V. , Pankaj  , Shakil Najam Akhtar 

TITLE=Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

JOURNAL=Frontiers in Chemistry

VOLUME=Volume 12 - 2024

YEAR=2024

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2024.1389848

DOI=10.3389/fchem.2024.1389848

ISSN=2296-2646

ABSTRACT=A series of 16 novel prenylated chalcones (5A-5P) was synthesized by microwave assisted green synthesis using 5-prenyloxy-2-hydroxyacetophenone and different benzaldehydes. A comparison between microwave and conventional methods was also made between the reaction times and yields of all compounds, the corresponding time in microwave and conventional method were 1 to 4 minutes and 12 to 48 hours, respectively. The synthesized compounds were characterized by different spectroscopic techniques, including IR, 1 H-NMR, 13 C-NMR and LC-HRMS. Antifungal activity of all the compounds was evaluated against Sclerotium rolfsii and Fusarium oxysporum, under in vitro conditions, supported by Structure Activity Relationship (SAR) and molecular docking studies. Out of 16 compounds screened, 2'-Hydroxy-4-benzyloxy-5'-O-prenylchalcone (5P) possessed highest activity against both S. rolfsii and F. oxysporum, with ED50 of 25.02 and 31.87 mg L -1 , respectively.The molecular docking studies of the prenylated chalcones within the active sites of EF1α and RPB2 gene sequences and FoCut5a sequence as the receptors for S. rolfsii and F. oxysporum, respectively, revealed the importance of these compounds by suggesting the binding energies of the docked molecules ranging from -38.3538 to -26.6837 for S. rolfsii and -43.400 to -23.839 kcal/mol for F. oxysporum. It was further demonstrated by other docking parameters that these compounds form stable complexes with the protein molecules.