Please use this identifier to cite or link to this item: https://hdl.handle.net/10316/107467
Title: Petasis adducts of tryptanthrin – synthesis, biological activity evaluation and druglikeness assessment
Authors: Brandão, Pedro 
Marques, Carolina
Pinto, Eugénia 
Pineiro, Marta 
Burke, Anthony J. 
Issue Date: 2021
Publisher: Royal Society of Chemistry
Project: info:eu-repo/grantAgreement/FCT/POR_CENTRO/PD/BD/128490/2017/PT/Sustainable Asymmetric Catalytic Synthesis of Novel Oxindole Hybrids with Potential Biological Activity 
info:eu-repo/grantAgreement/FCT/UIDB/00313/2020 
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/50006/2020/PT/Associated Laboratory for Green Chemistry - Clean Technologies and Processes 
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/04423/2020/PT/Interdisciplinary Centre of Marine and Environmental Research 
info:eu-repo/grantAgreement/FCT/REEQ/481/QUI/2006 
info:eu-repo/grantAgreement/RECI/QEQ-QFI/0168/2012 
info:eu-repo/grantAgreement/CENTRO-07-CT62-FEDER-002012 
Serial title, monograph or event: New Journal of Chemistry
Volume: 45
Issue: 32
Abstract: Tryptanthrin is a valuable tetracyclic alkaloid, which displays a wide variety of biological activities. The application of this type of scaffold as a starting material for the discovery of new drug candidates is of major importance in medicinal chemistry. In this work, we report one of the few examples of tryptanthrin-based multicomponent reaction approaches for drug discovery, and the first using the Petasis reaction. The optimized BINOL-catalyzed reaction conditions allowed the synthesis of a library of new tryptanthrin derivatives bearing considerable structural diversity. An asymmetric version was also established, achieving the desired enantiomerically pure derivative with 99% ee and 71% yield. The resulting library was screened against one Gram-positive and one Gram-negative bacteria, two yeasts, and three filamentous and four dermatophyte fungal strains with clinical relevance, with compound 5bea displaying moderate fungicidal activity.
URI: https://hdl.handle.net/10316/107467
ISSN: 1144-0546
1369-9261
DOI: 10.1039/D1NJ02079J
Rights: embargoedAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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