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Synthesis and comparative antibacterial studies of some benzylidene monosaccharide benzoates

Year 2015, Volume: 2 Issue: 4, 12 - 21, 11.03.2015
https://doi.org/10.18596/jotcsa.83708

Abstract

Some 4,6-O-benzylidene protected 2,3-di-O-benzoates of methyl a-D-glucopyranoside and methyl a-D-mannopyranoside were prepared. All the compounds (1-7) were screened for in vitro antibacterial activity study against ten human pathogenic bacteria. The study revealed that the benzoylated mannopyranosides (5-7) are more prone towards antibacterial functionalities than that of the glucopyranosides (2-3).

References

  • Guthrie RD, Honeyman J. An Introduction to the Chemistry of Carbohydrates. 1968;3rd ed. Oxford (UK).
  • Moyer BG, Pfeffer PE, Moniot JL, Shamma M, Gustine DL. Corollin, coronillin and coronarian: Three new 3-nitropropanoyl-D-glucopyranoses from Coronilla varia. Phytochemistry 1977;16:375-377. doi: org/10.1016/0031-9422(77)80068-X.
  • Tsuda Y, Haque ME. Regioselective introduction of p-coumaroyl group to -L-arabinopyranosides: Total synthesis of inundoside-G and inundoside-D1. Chemical and Pharmaceutical Bulletin 1983;31:1437-1439. doi: org/10.1248/cpb.31.1437.
  • Andry C, Wylde R, Laffite C, Privat G, Winternitz I. Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapumgenistae. Phytochemistry 1982;21:1123-1127. doi: org/10.1016/S0031-9422(00)82429-2.
  • Matin MM. Synthesis and antimicrobial study of some methyl 4-O-palmitoyl--L-rhamnopyranoside derivatives. Orbital: The Electronic Journal of Chemistry 2014;6(1):20-28.
  • Gupta R, Paul S, Gupta AK Kachroo PL, Bani S. 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 1997;36(B):707-710.
  • Matin MM, Bhuiyan MMH, Afrin A, Debnath DC. Comparative antimicrobial activities of some monosaccharide and disaccharide acetates. J. Sci. Res. 2013;5(3): 515-525. doi: org/10.3329/jsr.v5i3.15695.
  • Matin M, Bhuiyan MMH, Debnath DC, Manchur MA. Synthesis and comparative antimicrobial studies of some acylated D-glucofuranose and D-glucopyranose derivatives. International Journal of Bioscience 2013;3(8):279-287. doi: .org/10.12692/ijb/3.8.279-287.
  • Matin MM, Bhuiyan MMH, Azad AKMS. Synthesis and antimicrobial evaluation of some n-butyl - and -D-glucopyranoside derivatives. RGUHS Journal of Pharmaceutical Science 2013;3:53-59. doi: 10.5530/rjps.2013.1.8.
  • Demchenko AV, Pornsuriyasak P, de Meo C. Acetal protecting groups in the organic laboratory: Synthesis of methyl 4,6-O-benzylidene-α-D-glucopyranoside. Journal of Chemical Education 2006;83(5):782-784. doi: 10.1021/ed083p782.
  • Tusda Y, Haque ME, Yosimoto K. Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates. Chemical and Pharmaceutical Bulletin 1983;31(5): 1612-1624. doi: org/10.1248/cpb.31.1612.
  • Bauer AW, Kirby WMM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clinical Pathology. 1966;45(4): 493-496.
  • Nashed MA, Anderson L. Organotin derivatives and the selective acylation and alkylation of the equatorial hydroxy group in a vicinal, equatorial-axial pair. Tetrahedron Letters 1976;17(39):3503-3506. doi: 10.1016/S0040-4039(00)71342-6.
  • Kim YM, Farrah S, Baney RH. Structure-antimicrobial activity relationship for silanols, a new class of disinfectants, compared with alcohols and phenols. International Journal of Antimicrobial Agents 2007;29(2):217-222. doi: org/10.1016/j.ijantimicag.2006.08.036.
  • Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P, Clercq ED, Pannecouque C, Balzarini J. Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of N2-acyl isonicotinic acid hydrazide derivatives. Medicinal Chemistry 2013;9(1):53-76. doi: org/10.2174/157340613804488404.

Bazı benziliden monosakkarit benzoatların sentezi ve karşılaştırmalı antibakteriyel çalışmaları

Year 2015, Volume: 2 Issue: 4, 12 - 21, 11.03.2015
https://doi.org/10.18596/jotcsa.83708

Abstract

Metil a-D-glukopiranozid ve metil a-D-mannopiranozidin 4,6-O-benziliden ile korunmuş 2,3-di-O-benzoatları hazırlanmıştır. Bütün bileşikler (1-7) on adet insana karşı patojenik bakteriye karşı in vitro antibakteriyel aktivite çalışması için görüntülenmiştir. Çalışmaya göre, benzoillenmiş mannopiranozidler (5-7) glukopiranozidlere (2-3) karşı antibakteriyel işlevsellik bakımından daha narindir.

References

  • Guthrie RD, Honeyman J. An Introduction to the Chemistry of Carbohydrates. 1968;3rd ed. Oxford (UK).
  • Moyer BG, Pfeffer PE, Moniot JL, Shamma M, Gustine DL. Corollin, coronillin and coronarian: Three new 3-nitropropanoyl-D-glucopyranoses from Coronilla varia. Phytochemistry 1977;16:375-377. doi: org/10.1016/0031-9422(77)80068-X.
  • Tsuda Y, Haque ME. Regioselective introduction of p-coumaroyl group to -L-arabinopyranosides: Total synthesis of inundoside-G and inundoside-D1. Chemical and Pharmaceutical Bulletin 1983;31:1437-1439. doi: org/10.1248/cpb.31.1437.
  • Andry C, Wylde R, Laffite C, Privat G, Winternitz I. Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapumgenistae. Phytochemistry 1982;21:1123-1127. doi: org/10.1016/S0031-9422(00)82429-2.
  • Matin MM. Synthesis and antimicrobial study of some methyl 4-O-palmitoyl--L-rhamnopyranoside derivatives. Orbital: The Electronic Journal of Chemistry 2014;6(1):20-28.
  • Gupta R, Paul S, Gupta AK Kachroo PL, Bani S. 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 1997;36(B):707-710.
  • Matin MM, Bhuiyan MMH, Afrin A, Debnath DC. Comparative antimicrobial activities of some monosaccharide and disaccharide acetates. J. Sci. Res. 2013;5(3): 515-525. doi: org/10.3329/jsr.v5i3.15695.
  • Matin M, Bhuiyan MMH, Debnath DC, Manchur MA. Synthesis and comparative antimicrobial studies of some acylated D-glucofuranose and D-glucopyranose derivatives. International Journal of Bioscience 2013;3(8):279-287. doi: .org/10.12692/ijb/3.8.279-287.
  • Matin MM, Bhuiyan MMH, Azad AKMS. Synthesis and antimicrobial evaluation of some n-butyl - and -D-glucopyranoside derivatives. RGUHS Journal of Pharmaceutical Science 2013;3:53-59. doi: 10.5530/rjps.2013.1.8.
  • Demchenko AV, Pornsuriyasak P, de Meo C. Acetal protecting groups in the organic laboratory: Synthesis of methyl 4,6-O-benzylidene-α-D-glucopyranoside. Journal of Chemical Education 2006;83(5):782-784. doi: 10.1021/ed083p782.
  • Tusda Y, Haque ME, Yosimoto K. Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates. Chemical and Pharmaceutical Bulletin 1983;31(5): 1612-1624. doi: org/10.1248/cpb.31.1612.
  • Bauer AW, Kirby WMM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clinical Pathology. 1966;45(4): 493-496.
  • Nashed MA, Anderson L. Organotin derivatives and the selective acylation and alkylation of the equatorial hydroxy group in a vicinal, equatorial-axial pair. Tetrahedron Letters 1976;17(39):3503-3506. doi: 10.1016/S0040-4039(00)71342-6.
  • Kim YM, Farrah S, Baney RH. Structure-antimicrobial activity relationship for silanols, a new class of disinfectants, compared with alcohols and phenols. International Journal of Antimicrobial Agents 2007;29(2):217-222. doi: org/10.1016/j.ijantimicag.2006.08.036.
  • Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P, Clercq ED, Pannecouque C, Balzarini J. Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of N2-acyl isonicotinic acid hydrazide derivatives. Medicinal Chemistry 2013;9(1):53-76. doi: org/10.2174/157340613804488404.
There are 15 citations in total.

Details

Primary Language Turkish
Journal Section Articles
Authors

Mohammed Matin

M.m.h. Bhuiyan This is me

Md. Hossain This is me

Mohammad Or Roshid This is me

Publication Date March 11, 2015
Submission Date February 8, 2015
Published in Issue Year 2015 Volume: 2 Issue: 4

Cite

Vancouver Matin M, Bhuiyan M, Hossain M, Or Roshid M. Bazı benziliden monosakkarit benzoatların sentezi ve karşılaştırmalı antibakteriyel çalışmaları. JOTCSA. 2015;2(4):12-21.

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