Abstract
In the racemic title compound, C23H20N2O4S, the sulfur atom is attached equatorially to the sugar ring with unequal S-C bonds, viz.: S-Cs = 1.808 (2) and S-Cp = 1.770 (2) Å (s = sugar, p = pyrid-yl). The dihedral angles between the pyridine ring and its attached phenyl groups are 42.24 (8) and 6.37 (14)°. In the crystal, a system of classical O-H⋯O and O-H⋯(O,O) hydrogen bonds links the mol-ecules to form tube-like assemblies propagating parallel to the c-axis direction. Weak C-H⋯N inter-actions are also observed.
Highlights
In the racemic title compound, C23H20N2O4S, the sulfur atom is attached equatorially to the sugar ring with unequal S—C bonds, viz.: S—Cs = 1.808 (2) and S—Cp = 1.770 (2) A (s = sugar, p = pyridyl)
The dihedral angles between the pyridine ring and its attached phenyl groups are 42.24 (8) and 6.37 (14)
It has been shown that thioglycosides involving pyridine and dihydropyridine groups exert inhibitory effects on both DNA-containing viruses and inhibitors of protein glycosylation (Agrawal et al, 2017; Elgemeie et al, 2010; Masoud et al, 2017)
Summary
Nucleoside analogues of pyrimidines and purines have been shown to be effective as chemical therapeutic agents against cancer cells (Yoshimura et al, 2000; Elgemeie et al, 2016, 2017a,b). It has been shown that thioglycosides involving pyridine and dihydropyridine groups exert inhibitory effects on both DNA-containing viruses and inhibitors of protein glycosylation (Agrawal et al, 2017; Elgemeie et al, 2010; Masoud et al, 2017). Based on these significant biological findings and with the aim of identifying new potent chemotherapeutics as new anticancer agents with improved pharmacological and safety profiles, we have prepared several new non-classical thioglycosides containing the pyridine ring. Has too narrow an angle to be considered a hydrogen bond
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