Synthesis and comparative antimicrobial studies of some acylated d-glucofuranose and d-glucopyranose derivatives

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Synthesis and comparative antimicrobial studies of some acylated d-glucofuranose and d-glucopyranose derivatives

Mohammed M. Matin, M. M. H. Bhuiyan, Dulal C. Debnath, M. A. Manchur
Int. J. Biosci.3( 8), 279-287, August 2013.
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Some acylated D-glucofuranose (2, 3, 5, 6) and D-glucopyranose (8, 9) derivatives were prepared by direct acylation method for comparative antimicrobial studies. All the compounds (19) were screened for in vitro antibacterial activity against ten human pathogenic bacteria and antifungal activity against four pathogenic fungi. The study revealed that the D-glucopyranose derivatives were more prone towards antimicrobial functionality than that of the D-glucofuranose derivatives.


Guthrie RD, Honeyman J. 1968. An Introduction to the Chemistry of Carbohydrates. 3rd ed. Oxford, UK.

Moyer BG, Pfeffer PE, Moniot JL, Shamma M, Gustine DL. 1977. Corollin, coronillin and coronarian: Three new 3-nitropropanoyl-D-glucopyranoses from Coronilla varia. Phytochemistry 16, 375-377.

Tsuda Y, Haque ME, 1983. Regioselective introduction of p-coumaroyl group to a-L-arabino-pyranosides. Total synthesis of Inundoside-G and Inundoside-D1. Chemical and Pharmaceutical Bulletin (Japan) 31, 1437-1439.

Andry C, Wylde R, Laffite C, Privat G, Winternitz I. 1982. Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapumgenistae. Phytochemistry 21, 11231127.

Kabir AKMS, Matin MM, Ali M, Anwar MN. 2003. Comparative studies on selective acylation and antimicrobial activities of some D-glucofuranose derivatives. Journal of Bangladesh Academy of Science 27, 43-50.

Gupta R, Paul S, Gupta AK Kachroo PL, Bani 1997. Synthesis and biological activities of some 2- substituted phenyl-3-(3-alkyl/aryl-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiazolo-6-yl)-indoles. Indian Journal of Chemistry 36(B), 707-710.

Matin MM, Bhuiyan MMH, Azad AKMS. 2013. Synthesis and antimicrobial evaluation of some n-butyl a and b-D-glucopyranoside derivatives. RGUHS Journal of Pharmaceutical Science (India) 3, 53-59. http://dx.doi.10.5530/rjps.2013.1.8

Matin MM, Ibrahim M, Rahman MS. 2008. Antimicrobial evaluation of methyl 4-O-acetyl-a-L-rhamnopyranoside derivatives. Chittagong University Journal of Biological Science 3, 33-43.

Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. 1996. Vogel′s Text Book of Practical Organic Chemistry. England: Addision Wesley Longman Ltd, 654.

Horton D, Jewell JS, Prihar HS. 1968. Reaction of 3-Op-bromophenylsulfonyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose with dimethylamine. Canadian Journal of Chemistry 46, 1580-1582. http://dx.doi.pdf/10.1139/v68-261

Gramera RE, Park A, Whistler RL.  1963.  A convenient preparation of 1,2-mono-O-isopropylidene-a-D-glucofuranose. Journal of Organic Chemistry 28, 3230-3231. http://dx.doi.10.1021/jo01046a518

Barker GR. 1963. Methods in Carbohydrate Chemistry. Whistler RL, Wolform ML, ed. Vol 2, New York: Academic Press Inc., 168.

Bauer AW, Kirby WMM, Sherris JC, Turck M. 1966. Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology 45, 493-496.

Grover RK, Moore JD. 1962. Toximetric studies of fungicides against the brown root organisms, Sclerotinia fructicola and S. laxa. Phytopathology 52, 876-880.

Miah MAT, Ahmed HU, Sharma NR, Ali A, Miah SA. 1990. Antifungal activity of some plant extracts. Bangladesh Journal of Botany 19, 5-10.