Xanthenes in Medicinal Chemistry - Synthetic strategies and biological activities

• Type: Another Publication in an International Scientific Journal
• Date: 2021

Authors

Maia, M (Author) Other; Resende, DISP (Author) Other; Duraes, F (Author) Other; Pinto, MMM (Author) Other; Emilia Sousa (Author) FFUP

Journal

Title: European Journal of Medicinal Chemistry

Vol. 210

ISSN: 0223-5234

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 11 Citations

Scopus - 13 Citations

Other information

Authenticus ID: P-00T-7JA

DOI: 10.1016/j.ejmech.2020.113085

Abstract (EN): Background: Xanthenes are a special class of oxygen-incorporating tricyclic compounds. Structurally related to xanthones, the presence of different substituents in position 9 strongly influences their physical and chemical properties, as well as their biological applications. This review explores the synthetic methodologies developed to obtain 9H-xanthene, 9-hydroxyxanthene and xanthene-9-carboxylic acid, as well as respective derivatives, from simple starting materials or through modification of related structures. Azaxanthenes, bioisosteres of xanthenes, are also explored. Efficiency, safety, ecological impact and applicability of the described synthetic methodologies are discussed. Synthesis of multi-functionalized derivatives with drug-likeness properties are also reported and their activities explored. Synthetic methodologies for obtaining (aza)xanthenes from simple building blocks are available, and electrochemical and/or metal free procedures recently developed arise as greener and efficient methodologies. Nonetheless, the synthesis of xanthenes through the modification of the carbonyl in position 9 of xanthones represents the most straightforward procedure to easily obtain a variety of (aza)xanthenes. (Aza)xanthene derivatives displayed biological activity as neuroprotector, antitumor, antimicrobial, among others, proving the versatility of this nucleus for different biological applications. However, in some cases their chemical structures suggest a lack of pharmacokinetic properties being associated with safety concerns, which should be overcome if intended for clinical evaluation.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 29