Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4[vprime]-Dimethylxanthotoxol 2,3,4,6-tetra-O-Acetyl-[beta]-D-glucoside

An improved synthesis for 4,4[vprime]-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-[beta]-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 5...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2019-01, Vol.38 (3), p.179
Main Authors: Chen, Chao-Yue, Yang, Ting-Hai, Pan, Chang-Duo, Wang, Xin
Format: Article
Language:English
Subjects:
Antifungal agents
Crystallography
Fungicides
Steric hindrance
Synthesis
Online Access:Get full text
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Summary:An improved synthesis for 4,4[vprime]-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-[beta]-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 54.820(22)° probably due to the steric hindrance caused by the bulky O-glucoside moiety, which prevents the molecules from packing via π···π stacking between the tricyclic cores. The antifungal screening data revealed that glucoside 1 had higher inhibition than its parent compound 4,4[vprime]-dimethylxanthotoxol and azoxystrobin against Rhizoctonia solani, Pyricularia grisea, and Alternaria alternate Japanese pear pathotype, with the inhibitory rates of 75.4, 65.7 and 70.1%, respectively, at the 50 µg/mL concentration.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2019.1609018