Paper Titles in Periodical
International Letters of Chemistry, Physics and Astronomy
Volume 64

Subscribe

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > Volume 64 > Benzenesulfonylation of Methyl...
Benzenesulfonylation of Methyl α-D-Glucopyranoside: Synthesis, Characterization and Antibacterial Screening
< Back to Volume

Benzenesulfonylation of Methyl α-D-Glucopyranoside: Synthesis, Characterization and Antibacterial Screening

Full Text PDF

Abstract:

A novel series of benzenesulfonyl derivatives of methyl α-D-glucopyranoside (1) were synthesized by reacting benzenesulfonyl chloride in pyridine followed by direct acylation method to yield 6-O-benzenesulfonyl derivative (2). In order to obtain newer products for antibacterial evaluation studies, the 6-O-benzenesulfonyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-11) containing a wide variety of functionalities in a single molecular framework. All the synthesized compounds have been confirmed by IR, 1H NMR and elemental analysis. These newly synthesized compounds were screened for in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that the acylated products exhibit moderate to good antibacterial activities. It was interesting to observe that the selected compounds were more sensitive against Gram-Ve bacteria than that of the Gram-+Ve bacterial strains.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 64)
Pages:
95-105
DOI:
https://doi.org/10.18052/www.scipress.com/ILCPA.64.95
Citation:
S. M.A. Kawsar et al., "Benzenesulfonylation of Methyl α-D-Glucopyranoside: Synthesis, Characterization and Antibacterial Screening", International Letters of Chemistry, Physics and Astronomy, Vol. 64, pp. 95-105, 2016
Online since:
February 2016
Authors:
Sarkar M.A. Kawsar, Samia S.B.S. Nishat, Mohammad A. Manchur, Yasuhiro Ozeki
Keywords:
Antibacterial, Glucopyranoside, Inhibition, Organisms, Spectroscopy, Synthesis
Export:
RIS, BibTeX, Text
Distribution:
Open Access

Creative Commons License
This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

[1] G. Alvarez-Manilla, L. Warren, T. Abney, J. Atward, P. Azadi, W.S. York, M. Pierce, R. Orlando, Tools for glycomics: relative quantitation of glycans by isotopic permethylation using 13CH3I, Glycobiology 17 (2007) 677-687.

[2] S. Timmer, L. Stocker, H. Seeberger, Probing glycomics, Curr. Opin. Chem. Biol. 11 (2007) 59-65.

[3] A. Varki, Glycan-based interactions involving vertebrate sialic-acid-recognizing proteins, Nature 446 (2007) 1023-1029.

[4] R. Kannagi, M. Izawa, T. Koike, K. Miyazaki, N. Kimura, Carbohydrate-mediated cell adhesion in cancer metastasis and angiogenesis, Cancer Sci. 95 (2004) 377-384.

[5] B. Catterall, L.M. Jones, G.A. Turner, Membrane protein glycosylation and CD44 content in the adhesion of human ovarian cancer cells to hyaluronan, Clin. Exp. Metastasis 17 (1999) 583-591.

[6] R. Takano, E. Muchmore, J.W. Dennis, Sialylation and malignant potential in tumor cell glycosylation mutants, Glycobiology 4 (1994) 665-674.

[7] E. Taylor, K. Drickamer, Introduction to Glycobiology, second ed., Oxford University Press, New York, (2006).

[8] A. Alavi, S. Axford, Glycoimmunology, Plenum Press, New York, (1995).

[9] J.M. Williams, A.C. Richardson, Selective acylation of pyranosides-I. benzoylation of methyl α-D-glycopyranosides of mannose, glucose and galactose, Tetrahedron 23 (1967) 1369-1378.

[10] C. Andry, R. Wylde, C. Laffite, G. Privat, I. Winternitz, Structures of verbascoside and orobanchoside caffeic acid sugar esters from Orobanche rapumgenistae, Phytochemistry 21 (1982) 1123-1127.

[11] D. Wagner, J.P.H. Verheyden, J.G. Moffatt, Preparation and synthetic utility of some organotin derivatives of nucleosides, J. Org. Chem. 39 (1974) 24-30.

[12] R.M. Munavu, H.H. Szmant, Selective formation of 2 esters of some methyl α-D-hexopyranosides via dibutylstannylene derivatives, J. Org. Chem. 41 (1976) 1832-1835.

[13] J.J. Willard, J.S. Brimacombe, R.P. Brueton, The synthesis of 3-O-[(benzylthio)carbonyl]-β-D-glucopyranose and methyl 2, 4, 6-tri-O-α and β-D-glucopyranosides, Cand. J. Chem. 42 (1964) 2560-2567.

[14] X.P. Hui, C.H. Chu, Z.Y. Zhang, Q. Wang, Q. Zhang, Synthesis and antibacterial activities of 1, 3, 4-oxadiazole derivatives 5-methylisoxazole moiety, Ind. J. Chem. 41 (2002) 2176-2179.

[15] P. Rani, V.K. Srivastav, A. Kumar, Synthesis and anti-inflammatory activity of some new 2, 3-disubstituted 6-monosubstituted quinazolin-4(3H)-ones, Ind. J. Chem. 41B (2002) 2642-2646.

[16] K.D. Patel, B.D. Mistry, K.R. Desai, Synthesis and antimicrobial activity of 1, 2, 4-triazoles, J. Ind. Chem. Soc. 79 (2002) 964-965.

[17] M.M. Ghorab, Z.H. Ismail, S.M.A. Gawad, A.A. Aziem, Antimicrobial activity of amino acid, imidazole, and sulfonamide derivatives of pyrazolo[3, 4-d]pyrimidine, Heteroatom. Chem. 15 (2004) 57-62.

[18] R. Gupta, S. Paul, A.K. Gupta, P.L. Kachroo, S. Bani, 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, Ind. J. Chem. 36 (1997) 707-710.

[19] A.K.M.S. Kabir, M. Matin, M.A.U. Mridha, S.M. Shahed, Antifungal activities of some methyl 6-O-trityl-D-mannopyranosides, Chittagong Univ. J. Sci. 22 (1998) 41-46.

[20] A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S. Rahman, M.E. Chowdhury, Antimicrobial screening studies of some derivatives of methyl -D-glucopyranoside, Pak. J. Sci. Ind. Res. 52 (2009) 138-142.

[21] A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.R. Islam and M.S. Rahman, Biological evaluation of some mannopyranoside derivatives, Bull. Pure Appl. Sci. 23 (2004) 83-91.

[22] S.M.A. Kawsar, M.O. Faruk, M.S. Rahman, Y. Fujii, Y. Ozeki, Regioselective synthesis, characterization and antimicrobial activities of some new monosaccharide derivatives, Sci. Pharm. 82 (2014) 01-20.

[23] S.M.A. Kawsar, T. Hasan, S.A. Chowdhury, M.M. Islam, M.K. Hossain, M.A. Manchur, Synthesis, spectroscopic characterization and in vitro antibacterial screening of some D-glucose derivatives, Int. J. Pure Appl. Chem. 8 (2013) 125-135.

[24] S.M.A. Kawsar, A.K.M.S. Kabir, M.M.R. Bhuiyan, J. Ferdous, M.S. Rahman, Synthesis, characterization and microbial screening of some new methyl 4, 6-O-(4-methoxybenzylidene)-D-glucopyranoside derivatives, J. Bang. Acad. Sci. 37 (2013) 145-158.

[25] S.M.A. Kawsar, A.K.M.S. Kabir, M.M.R. Bhuiyan, M.M. Manik, Synthesis and characterization of methyl 4, 6-O-benzylidene-D-glucopyranoside derivatives, J. Bang. Chem. Soc. 25 (2012) 101-109.

[26] A.K.M.S. Kabir, M.M. Matin, A.F.M. Sanaullah, M.A. Sattar, M.S. Rahman, Antimicrobial activities of some lyxoside derivatives, Bang. J. Microb. 18 (2001) 89-95.

[27] S.M.A. Kawsar, A.K.M.S. Kabir, M.M. Manik. M.K. Hossain, M.N. Anwar, Antibacterial and mycelial growth inhibition of some acylated derivatives of D-glucopyranoside, Int. J. Biosci. 2 (2012) 66-73.

[28] A.K.M.S. Kabir, P. Dutta, M. Anwar, Biological evaluation of some acylated derivatives of D-mannose, Pak. J. Biol. Sci. 7 (2004) 1730-1734.

[29] A.K.M.S. Kabir, M.M. Matin, A. Hossain, M.A. Sattar, Synthesis and antimicrobial activities of some rhamnopyranoside derivatives, J. Bang. Chem. Soc. 16 (2003) 85-93.

[30] A.W. Bauer, W.M.M. Kirby, J.C. Sherris, M. Turck, Antibiotic susceptibility testing by a standardized single disc method, Am. J. Clin. Pathol. 45 (1966) 439-476.

[31] M.A.T. Miah, H.U. Ahmed, N.R. Sharma, A. Ali, S.A. Miah, Antifungal activity of some plant extracts, Bang. J. Bot. 19 (1990) 05-10.

Show More Hide
Cited By:
This article has no citations.