Novel Methyl 4,6-O-Benzylidene--D-Glucopyranoside Derivatives: Synthesis, Structural Characterization and Evaluation of Antibacterial Activities
Carbohydrates are the most abundant and the most diverse biopolymers in nature. Due to the importance of carbohydrates it is necessary to develop a new method for the synthesis of carbohydrate based drugs of the current global situation for health and disease. In this present work we demonstrate the synthesis of methyl 4,6-O-benzylidene--Dglucopyranoside derivatives by direct acylation method. The structures of the newly prepared compounds have been characterized and elucidated using various physico-chemical and spectroscopic methods including elemental analysis, melting point determination, infrared and proton NMR spectroscopy. A number of acyl derivatives were prepared in order to obtain a series of newer components for antibacterial screening experiments. These acylated derivatives were evaluated for in vitro antibacterial screening studies against four human pathogenic bacteria by disc diffusion method.
___
- 1.O.Gornik, J. Dumić, M. Flögel, G. Lauc, Glycoscience a new
frontier in rational drug design, Acta Pharm., 56 (2006) 19-
30.
- 2. J. Finkelstein, Editor, Glycochemistry and
glycobiology. Nature, 446 (2007) 999-1051.
- 3. G. Thanh Le, G. Abbenante, B. Becker, M. Grathwohl, J.
Halliday, G. Tometzki, J. Zuegg, W. Meutermans, Molecular
diversity through sugar scaffolds, Drug Discov. Today, 8
(2003) 701-709.
- 4. C.M. Nogueira, B.R. Parmanhan, P.P. Farias, A.G. Corrêa.
The growing importance of carbohydrates in medicinal
chemistry, Rev. Virtual Quim., 1 (2009) 149-159.
- 5. D.T. Nguyen, T.D. Hoang, T.D. Vu, M.T. Phan, V.Q.
Nguyen, Synthesis and antibacterial and antifungal
activities of N-(tetra-O-acetyl-β-d-glucopyranosyl)
thiosemicarbazones of substituted 4-formylsydnones,
Chem. Central J., 9 (2015) 60-74.
- 6. W. Chi-Huey, (Ed.) Carbohydrate-based drug discovery,
Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2003.
- 7. Y. Shen, Y. Sun, Z. Sang, C. Sun, Y. Dai, Y. Deng, Synthesis,
characterization, antibacterial and antifungal evaluation of
novel monosaccharide esters, Molecules, 17 (2012) 8661-
8673.
- 8. A. Aboelmagd, A.I.A. Ibrahim, M.S.S. Ezzeldin, M.
Abdel-Razik, Synthesis and antifungal activity of some
2benzothiazolylthioacetyl amino acid and peptide
derivatives, ARKIVOC (IX) (2011) 337-353.
- 9. S.M.A. Kawsar, M. Khaleda, A. Refat, M.A. Manchur, Y.
Koide, Y. Ozeki, Infrared, 1H-NMR spectral studies of some
methyl 6-O-myristoyl-α-D-glucopyranoside derivatives:
assessment of antimicrobial effects, Int. Lett. Chem. Phys.
Astron., 58 (2015) 122-136.
- 10. M.A. Sofan, B.S. Samy, H.S. Kandeel, Antimicrobial activity
of newly synthesized thiadiazoles, 5-benzyl-2Htetrazole and
their nucleosides, Der Pharm. Chemica, 4 (2012) 1064-1073.
- 11. 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.
- 12. Y. Tsuda, E. Haque, Regioselective introduction of
p-coumaroyl group to α-L-arabinopyranosides. Total
synthesis of inundoside-G and inundoside-D1, Chem. Pharm.
Bull., 31 (1983) 1437-1439.
- 13. M. Itoh, D. Hagiwara, J. Notani, A simple and mild
esterification method for carboxylic acids using sulfonatetype
coupling reagents, Synthesis, 7 (1975) 456-458.
- 14. Y. Kondo, Selective benzoylation of methyl α- and β-Dxylopyranoside,
Carbohydr. Res., 107 (1982) 303-311.
- 15. J.M. Sugihara, Relative reactivities of hydroxyl groups of
carbohydrates, Adv. Carbohydr. Chem., 8 (1953) 1-44.
- 16. A.K.M.S. Kabir, P. Dutta, M.N. Anwar, Synthesis of some new
derivatives of D-mannose, Chittagong Univ. J. Sci., 29 (2005)
01-08.
- 17. M. Ichinari, K. Nakayama, Y. Hayase, Synthesis of
2,4-dioxoimidazolidines from 2-arylimino-1,3-triazines and
their antifungal activity, Heterocycles (Tokyo), 27 (1988)
2635-2641.
- 18. N.G. Gawande, M.S. Shingare, Synthesis of some
thiazolylthiosemicarbazides, triazoles, oxazoles, thiadiazoles
& their microbial activity, Ind. J. Chem., 26 (1987) 387-389.
- 19. 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.
- 20. H. Singh, K.N. Shukla, R. Dwivedi, L.D.S. Yadav, Clycloaddition
of 4-amino-3-mercepto-1,2,4-triazole to heterocumulenes
and antifungal activity of the resulting 1,2,4-triazolo[3,4-
c]-1,2-dithia-4,5-diazines, J. Agric. Food. Chem., 38 (1990)
1483-1486.
- 21. S.M.A. Kawsar, M.M. Islam, S.A. Chowdhury, T. Hasan,
M.K. Hossain, M.A. Manchur, Y. Ozeki, Design and newly
synthesis of some 1,2-O-isopropylidene-α-D-glucofuranose
derivatives: characterization and antibacterial screening
studies, Hacett. J. Biol. Chem., 41 (2013) 195-206.
- 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) 1-20.
- 23. A.K.M.S. Kabir, M.M. Matin, S.M.A. Kawsar, Synthesis
and antibacterial activities of some uridine derivatives,
Chittagong Univ. J. Sci., 22 (1998) 13-18.
- 24. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, S. Hossain,
Synthesis and characterization of some uridine derivatives,
J. Bang. Chem. Soc., 16 (2003) 6-14.
- 25. S.M.A. Kawsar, J. Ferdous, G. Mostafa, M.A. Manchur, A
synthetic approach of D-glucose derivatives: spectral
caracterization and antimicrobial studies, Chem. Chem.
Technol. J., 8 (2014) 19-27.
- 26.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)-α-D-glucopyranoside derivatives, J.
Bang. Acad. Sci., 37 (2013) 145-158.
- 27. S.M.A. Kawsar, M.M. Rahman, M. Islam, M.A. Manchur,
H. Imtiaj, S. Rajia, An in vitro assessment of antibacterial,
antifungal and cytotoxic effects of D-glucopyranoside
derivatives, Int. J. Biosci., 12 (2018) 408-416.
- 28. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S.
Rahman, M.E. Chowdhury, Antimicrobial screening of some
derivatives of methyl α-D-glucopyranoside, Pak. J. Sci. Ind.
Res., 52 (2009) 138-142.
- 29. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, B.
Banu, Synthesis of some new derivatives of methyl
4,6-O-cyclohexylidene-α-D-glucopyranoside, J. Bang. Chem.
Soc., 21 (2008) 72-80.
- 30. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.R.
Islam, M.S. Rahman, Biological evaluation of some
mannopyranoside derivatives, Bull. Pure Appl. Sci., 23
(2004) 83-91.
- 31. N.K. Richtmeyer, Methods in carbohydrate chemistry, Meth.
Carbohydr. Chem., Academic Press Inc. (New York), 1 (1962)
107-111.
- 32. 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.
- 33. 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.
- 34. A.K.M.S. Kabir, M.M. Matin, M.J. Alam, M.N. Anwar, Synthesis
and antimicrobial activities of some glucopyranoside
derivatives, Chittagong Univ. J. Sci., 23 (1999) 25-34.
- 35. S.M.A. Kawsar, I. Mariam, J. Sanjida, M.A. Manchur, I. Hasan,
R. Sultana, Evaluation of the antimicrobial activity and
cytotoxic effect of some uridine derivatives, Int. J. Biosci.,
12 (2018) 211-219.
- 36. S.M.A. Kawsar, A.A. Hamida, A,U, Sheikh, M.K. Hossain,
A.C. Shagir, A.F.M. Sanaullah, M.A. Manchur, I. Hasan, Y.
Ogawa, Y. Fujii, Y. Koide, Y. Ozeki, Chemically modified
uridine molecules incorporating acyl residues to enhance
antibacterial and cytotoxic activities, Int. J. Org. Chem., 5
(2015) 232-245.
- 37. S.M.A. Kawsar, U. Sharif, M.A. Manchur, Y. Fujii, Y. Ozeki,
Acylation of D-glucose derivatives over C5H5N: spectral
characterization and in vitro antibacterial activities, Int. J.
Biol. Chem., 9 (2015) 269-282.
- 38. S.M.A. Kawsar, S.S.B.S. Nishat, M.A. Manchur, Y. Ozeki,
Benzenesulfonylation of methyl α-D-glucopyranoside:
synthesis, characterization and antibacterial screening, Int.
Lett. Chem. Phys. Astron., 64 (2016) 95-105.
- 39. S.M.A. Kawsar, U. Sharif, S.S.B.S. Nishat, M.A. Manchur,
Y. Ozeki, Synthesis, characterization and antibacterial
susceptibility of some benzenesulfonyl and N-acetylsulfanilyl
derivatives of methyl α-D-glucopyranoside, Curr. Res. Chem.,
7 (2015) 21-33.
- 40. S.M.A. Kawsar, M.O. Faruk, G. Mostafa, M.S. Rahman,
Synthesis and spectroscopic characterization of some novel
acylated carbohydrate derivatives and evaluation of their
antimicrobial activities, Chem. Biol. Interface, 4 (2014) 37-47.
- 41. Y.M. Kim, S. Farrah, R.H. Baney, Structure-antimicrobial
activity relationship for silanols, a new class of disinfectants,
compared with alcohols and phenols, Int. J. Antimicrob.
Agents, 29 (2007) 217-222.
- 42. W.A. Hunt, The effects of aliphatic alcohols on the
biophysical and biochemical correlates of membrane
function, Adv. Exper. Med. Biol., 56 (1975) 195-210.
- 43. V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari,
E.D. Clercq, C. Pannecouque, J. Balzarini, Synthesis,
antimycobacterial, antiviral, antimicrobial activity and QSAR
studies of N2-acyl isonicotinic acid hydrazide derivatives,
Med. Chem., 9 (2013) 53-76.
- 44. 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.
- 45. S.M.A. Kawsar, A.K.M.S. Kabir, M.M.R. Bhuiyan, A. Siddiqa,
M.N. Anwar, Synthesis, spectral and antimicrobial screening
studies of some acylated D-glucose derivatives, Rajiv Gandhi
Univ. Health Sci. (RGUHS) J. Pharm. Sci., 2 (2012) 107-115