Infrared, ¹H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Abstract

ABSTRACT.This study was carried out to regioselective myristoylation of methyl α-Dglucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-Omyristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1 H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

“…2) of methyl α-D-glucopyranoside (1) using some non-traditional acylating agents namely, 4-t-butylbenzoyl chloride, 2-chlorobenzoyl chloride, 4-chlorobenzoyl chloride and benzoyl chloride. According to the well-known method i.e., direct acylation method (Kawsar et al, 2015;Kabir et al, 2005b), two series ( Fig. 1 and 2) were synthesized using methyl α-D-glucopyranoside as the starting material.…”

“…From our previous works (Kawsar et al, 2013a(Kawsar et al, , 2015Kabir et al, 2008Kabir et al, , 2009, it also observed that in many cases the combination of two or more acyl substituents in a single molecular framework enhances the biological profile manifold than their parent nuclei (Kabir et al, 2004(Kabir et al, , 2005aKawsar et al, 2012a). Encouraged by our own findings and also literature reports, it synthesized a series of methyl α-D-glucopyranoside (1) derivatives ( Fig.…”

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

“…A number of rarely used acylating agents were employed for this purpose (Scheme 2 and Table 1) and the physicochemical properties of the synthesized compounds were presented in the ( Table 2). The structure of the acylated products were ascertained by analyzing their FTIR and 1 H-NMR spectra [29]- [31]. In continuation of a project going on the carbohydrate and protein chemistry laboratory, we intended to prepare a series of uridine derivatives for use as test compounds for biological evaluation.…”

Simple and rapid synthesis of some nucleoside derivatives: structural and spectral characterization

“…By similar procedure, the lauroyl derivative (7) was obtained as semi-solid. The IR spectrum displayed absorption bands at 1758 cm Final confirmation of the structure of the compound 2 was provided by preparation of its 2,6-dichlorobenzoyl derivative (13). Reaction of compound 2 with 2,6-dichlorobenzoyl chloride in pyridine, as usual procedure gave the dichlorobenzoyl derivative (13) as pasty mass.…”

“…11,12 Of these, a direct method has been found to be the most encouraging method for acylation of carbohydrates and nucleosides. 13 It was found from the literature survey that nitrogen, sulphur and halogen containing heterocyclic compounds showed marked antimicrobial activities.…”