Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities

• Type: Article in International Scientific Journal
• Date: 2020

Authors

Loureiro, DRP (Author) Other; Magalhaes, AF (Author) Other; Jose X Soares (Author) FFUP; Pinto, J (Author) Other; Azevedo, CMG (Author) Other; Vieira, S (Author) Other; Henriques, A (Author) Other; Ferreira, H (Author) Other; Neves, N (Author) Other; Bousbaa, H (Author) Other; Salette Reis (Author) FFUP; Carlos Afonso (Author) FFUP; Pinto, MMM (Author) Other

Journal

Title: ChemMedChem

Vol. 15

Pages: 749-755

ISSN: 1860-7179

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 0 Citations

Scopus - 4 Citations

Other information

Authenticus ID: P-00R-YSR

DOI: 10.1002/cmdc.201900735

Abstract (EN): Natural products have always been an important source of new hits and leads in drug discovery, with the marine environment being regarded as a significant source of novel and exquisite bioactive compounds. Yicathins B and C are two marine-derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol/water system and a biomimetic model-based system. As the xanthonic nucleus is a "privileged structure", other biological activities were evaluated, namely antitumor and anti-inflammatory activities. An interesting anti-inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti-infective and anti-inflammatory) marine-inspired xanthone derivatives.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7