Novel styrylpyrazole-glucosides and their dioxolo-bridged doppelgangers: synthesis and cytotoxicity

• Type: Article in International Scientific Journal
• Date: 2019

Authors

Carreira, ARF (Author) Other; David M Pereira (Author) FFUP; Paula B Andrade (Author) FFUP; Patricia Valentao (Author) FFUP; Silva, AMS (Author) Other; Braga, SS (Author) Other; Silva, VLM (Author) Other

Journal

Title: New Journal of Chemistry

Vol. 43

Pages: 8299-8310

ISSN: 1144-0546

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 0 Citations

Scopus - 3 Citations

Other information

Authenticus ID: P-00Q-NWN

DOI: 10.1039/c9nj01021a

Abstract (EN): This paper describes the Koenigs-Knorr reaction of (E)-3(5)-(2-hydroxyphenyl)-4-styryl-1H-pyrazoles 1a-d with 2,3,4,6-tetra-O-acetyl--d-glucopyranosyl bromide, using silver carbonate (Ag2CO3) as base and silver triflate (AgOTf) as a promoter/activator in dry dichloromethane. Four per-O-acetylated pyrazole-coupled glucosides 2a-d, the target products of the reaction, were obtained in low yields (11-30%). Surprisingly, the main products of the reaction were new structures with the glucoside forming a dioxolo-bridge with the N-1 of the styrylpyrazole. These compounds 3a-d were obtained in moderate to good yields (39-52%). Compounds 2a-d and 3a-d were deacetylated, in mild conditions, using Amberlite (R) IRA-400(OH) in methanol, yielding deprotected pyrazole-glucoside conjugates 4a-d and 5b and 5c. The structures of the new compounds were assigned by 1D (H-1 and C-13) and 2D (COSY, HSQC, HMBC and NOESY) NMR experiments, as well as by MS and HRMS. The cytotoxicity of compounds 1a-d, 4a-d and 5b and 5c against AGS gastric adenocarcinoma cells and MRC-5 lung fibroblasts was evaluated.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 12