A Base-Catalyzed Cascade Route to Phenolic 6-Cyanopurines via O-Alkylformamidoximes

This review describes the non-exhaustive scenery of the synthesis of various biologically interesting pyrimidine annulated five-membered heterocyclic ring systems that have been appeared in the literature during the last two decades. During this period, different synthetic routes and various methodologies have been developed for the functionalization of pyrimidine ring towards the construction of five-membered heterocyclic rings. The aim of this review is to give an overview of the assorted methodologies that have been reported about the chemistry of construction of pyrimidines annulated nitrogen, oxygen and sulphur containing five-membered heterocycles.

show abstract

Phenolic Imidazole Derivatives with Dual Antioxidant/Antifungal Activity: Synthesis and Structure-Activity Relationship

Bettencourt

Castro

Silva

et al. 2019

View full text Add to dashboard Cite

Background: Previous publications show that the addition of a phenolic antioxidant to an antifungal agent, considerably enhances the antifungal activity. Objective: Synthesis of novel compounds combining phenolic units with linear or cyclic nitrogencontaining organic molecules with antioxidant/antifungal activity using methodologies previously developed in the group. Methods: Several N- [1,2-dicyano-2- (arylidenamino) vinyl]-O-alkylformamidoximes 3 were synthesized and cyclized to 4,5-dicyano-N- (N´-alcoxyformimidoyl)-2-arylimidazoles 4 upon reflux in DMF, in the presence of manganese dioxide or to 6-cyano-8-arylpurines 5 when the reagent was refluxed in acetonitrile with an excess of triethylamine. These compounds were tested for their antioxidant activity by cyclic voltammetry, DPPH radical (DPPH•) assay and deoxyribose degradation assay. The minimum inhibitory concentration (MIC) of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans, and against bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram negative). Their cytotoxicity was evaluated in fibroblasts. Results: Among the synthetised compounds, five presented higher antioxidant activity than reference antioxidant Trolox and from these compounds, four presented antifungal activity without toxic effects in fibroblasts and bacteria. Conclusion: Four novel compounds presented dual antioxidant/antifungal activity at concentrations that are not toxic to bacteria and fibroblasts. The active molecules can be used as an inspiration for further studies in this area.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

A Base-Catalyzed Cascade Route to Phenolic 6-Cyanopurines via O-Alkylformamidoximes

Cited by 3 publications

References 14 publications

ChemInform Abstract: A Base‐Catalyzed Cascade Route to Phenolic 6‐Cyanopurines via O‐Alkylformamidoximes.

ChemInform Abstract: A Base‐Catalyzed Cascade Route to Phenolic 6‐Cyanopurines via O‐Alkylformamidoximes.

Synthesis of Pyrimidine-Annulated Five-Membered Heterocycles: An Overview

Phenolic Imidazole Derivatives with Dual Antioxidant/Antifungal Activity: Synthesis and Structure-Activity Relationship

Contact Info

Product

Resources

About