Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Abstract

Methyl α-D-glucopyranoside was easily prepared by the treatment of D-glucose with anhydrous methyl alcohol in presence of hydrogen chloride at freezing temperature in good yield. Then N-acetylsulfanilylation of methyl α-D-glucopyranoside has been carried out by the direct method and afforded the 6-O-N-acetylsulfanilyl derivative in an excellent yield. In order to obtain newer products, the 6-O-N-acetylsulfanilyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were elucidated by Fourier Transform Infrared spectroscopy (FTIR), 1 H-NMR (Proton nuclear magnetic resonance) spectroscopy elemental and physicochemical properties analysis. All the newly synthesized D-glucose derivatives were tested for their in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that a good number of acylated products exhibited promising antibacterial activities. It is expected that the acylated derivatives of D-glucose may be considered as a potential source for developing new and better antibacterial agents against a number of pathogenic organism.

An efficient approach to the synthesis of thymidine derivatives containing various acyl groups: characterization and antibacterial activities

“…It is also known that if an active nucleus is linked to another active nucleus, the resulting molecule may possess greater potential for biological activity 13 . From our previous works we also observed that in many cases the combination of two or more acyl substituents in a single molecular framework enhances the biological activity manyfold than their parent nuclei [14][15][16][17][18] . Encouraged by our own findings and also literature reports, we synthesised a series of thymidine derivatives deliberately incorporating a wide variety of anticipated biologically active components to the deoxyribose moiety.…”

Microbial efficacy and two step synthesis of uridine derivatives with spectral characterization

“…It is also found that N, S and X containing substitution products showed marked antimicrobial activities i.e., enhance the biological activity of the parent compound 26,27 . Encouraged by literature reports and our own findings 28,29 , we synthesized some selectively acylated derivatives of uridine (1) (Scheme 1-2 & Table 1) containing various substituents in a single molecular framework and evaluated their antibacterial and antifungal activities using a variety of bacterial and fungal pathogens.…”

Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities

“…Results of an ongoing research work on selective acylation of carbohydrates [16] [17] and nucleosides [18] [19] and also evaluation of antimicrobial activities reveal that in many cases the combination of two or more aromatic or heteroaromatic nuclei [14]. It is also found that nitrogen, sulfur and halogen containing substitution products showed marked antimicrobial activities i.e., enhance the biological activity of the parent compound [20]- [25]. Encouraged by literature reports and our own findings, we synthesized a series of uridine derivatives (Scheme 1) deliberately incorporating a wide variety of probable biologically active components to the ribose moiety.…”