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International Letters of Chemistry, Physics and Astronomy
Volume 58
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Infrared, 1H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

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Abstract:

This study was carried out to regioselective myristoylation of methyl α-D-glucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-O-myristoyl-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 1H-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.

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Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 58)
Pages:
122-136
Citation:
S. M.A. Kawsar et al., "Infrared, 1H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects", International Letters of Chemistry, Physics and Astronomy, Vol. 58, pp. 122-136, 2015
Online since:
September 2015
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Cited By:

[1] S. Kawsar, S. Uddin, S. Nishat, M. A. Manchur, Y. Ozeki, "Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside", Current Research in Chemistry, Vol. 7, p. 21, 2015

DOI: https://doi.org/10.3923/crc.2015.21.33

[2] S. Kawsar, S. Uddin, M. Manchur, Y. Fujii, Y. Ozeki, "Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities", International Journal of Biological Chemistry, Vol. 9, p. 269, 2015

DOI: https://doi.org/10.3923/ijbc.2015.269.282

[3] S. Kawsar, H. Ara, S. Uddin, M. Hossain, S. Chowdhury, A. Sanaullah, M. Manchur, I. Hasan, Y. Ogawa, Y. Fujii, Y. Koide, Y. Ozeki, "Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities", International Journal of Organic Chemistry, Vol. 05, p. 232, 2015

DOI: https://doi.org/10.4236/ijoc.2015.54023