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Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents

Yıl 2015, Cilt: 43 Sayı: 4, 309 - 322, 01.11.2015

Öz

IIn the present investigation, a new series of methyl 6-O-cinnamoyl-α-D-glucopyranoside derivatives were synthesized by the reaction of methyl α-D-glucopyranoside 1 with various non-traditional acylating agents in pyridine at -5°C. For this purpose, firstly, selective cinnamoylation of methyl α-D-glucopyranoside 1 has been carried out by the direct acylation method and afforded the methyl 6-O-cinnamoyl-α-D-glucopyranoside 2 in good yield. Secondly, in order to obtain newer products for antimicrobial screening studies, the 6-O-cinnamoyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives 4-14 containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were characterized by IR, NMR and physicochemical properties analyses. All the compounds were evaluated for their in vitro antibacterial and antifungal activities using the disc diffusion and food poisoning methods. The study revealed that the compound methyl 6-O-cinnamoyl-2,3,4-tri-O-decanoyl-α-D-glucopyranoside 7 showed the highest inhibition activity against both Gram + B. subtilis and Gram - P. aeruginosa microorganisms. The tested compound methyl 6-O-cinnamoyl-2,3,4-tri-O-lauroyl-α-D-glucopyranoside 8 exhibited maximum mycelial growth inhibition against A. niger fungi. The acylated derivatives were found to be more effective against the fungal strains than those of the bacterial pathogens. This is the first report of the antimicrobial activity of the selected chemicals against the selected pathogens.

Kaynakça

  • 1. M.E. Taylor, K. Drickamer, Introduction to Glycobiology, Third edition, Oxford University Press, NY, USA (2011).
  • 2. A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, Essentials of Glycobiology, Second edition, Cold Spring Harbor Laboratory Press, Cold Spring, Harbor, NY, USA (2009).
  • 3. J.J. Willard, J.S. Brimacombe, R.P. Brueton, The synthesis of 3-O-[(benzylthio)carbonyl]-β-Dglucopyranose and methyl 2,4,6-tri-O- and β-Dglucopyranosides, Canad. J. Chem., 42 (1964) 2560.
  • 4. 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.
  • 5. R.M. Munavu, H.H. Szmant, Selective formation of 2 esters of some methyl-D-hexopyranosides via dibutylstannylene derivatives, J. Org. Chem., 41 (1976) 1832.
  • 6. H. Ishii, M. Nakamura, S. Seo, K. Tori, T. Tozoyo, Y. Yoshimura, Isolation, characterization and nuclear magnetic spectra of new saponins from the roots of Bupleurum falcatum L, Chem. Pharm. Bull., 28 (1980) 2367.
  • 7. Y. Tsuda, E. Haque, Regioselective introduction of p-coumaroyl group to -L-arabinopyranosides, Total synthesis of inundoside-G and inundoside-D1, Chem. Pharm. Bull., 31 (1983) 1437.
  • 8. 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.
  • 9. D.K. Byarugaba, Antimicrobial resistance in developing countries and responsible risk factors, Int. J. Antimicrob. Agents, 24 (2004) 105.
  • 10. S.J. Projan, D.M. Shlaes, Antibacterial drug discovery: is it all downhill from here, Clin. Microbiol. Infect, 10 (2004) 18.
  • 11. J.J. Barker, Antibacterial drug discovery and structure-based design, Drug Discov. Today, 11 (2006) 391.
  • 12. M.A. Bakht, M.S. Yar, S.G. Abdel-Hamid, S.I. Al Qasoumi, S. Abdul, Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives, Eur. J. Med. Chem., 45 (2010) 5862.
  • 13. R.S. Kumar, A.I. Adhulla, A. J.A. Nasser, J. Selvin, Synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives, J. Seb. Chem. Soc., 76 (2011) 01.
  • 14. H. Singh, K.N. Shukla, R. Dwivedi, L.D.S. Yadav, Cycloaddition of 4-amino-3-mercapto-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.
  • 15. 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-striazolo[3,4-b][1,3,4]thiazolo-6-yl)-indoles, Ind. J. Chem., 36 (1997) 707.
  • 16. M.M. Ghorab, Z.H. Ismail, S.M.A. Gaward, A.A. Aziem, Antimicrobial activity of amino acid, imidazole and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine, Heteroatom Chem., 15 (2004) 57.
  • 17. S.L. Gaonkar, K.M.L. Rai, B. Prabhuswamy, Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5- substituted-1,3,4-oxadiazoles, Eur. J. Med. Chem., 41 (2006) 841.
  • 18. Z.A. Kaplancikli, M.D. Altintop, G. Turan-Zitouni, A. Ozdemir, R. Ozic, G. Akalin, Synthesis, antimicrobial activity and cytotoxicity of novel oxadiazole derivatives, J. Enzyme Inhib. Med. Chem., 27 (2012) 51.
  • 19. Q. Zheng, X. Zhang, X. Ying, K. Cheng, Q. Jiao, H. Zhu, Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents, Bioorg. Med. Chem., 18 (2010) 7836.
  • 20. S. Dash, B.A. Kumar, J. Sing, B.C. Maiti, T.K. Maity, Synthesis of some novel 3,5-disubstituted 1,3,4-oxadiazole derivatives and anticancer activity on EAC animal model, Med. Chem. Res., 20 (2011) 1206.
  • 21. M. A. Ali, M. Shaharyar, Oxadiazole mannich bases: Synthesis and antimycobacterial activity, Bioorg. Med. Chem. Lett., 17 (2007) 3314.
  • 22. R.S. Kumar, S. Arunachalam, V.S. Periasamy, C.P. Preethy, A. Riyasdeen, M.A. Akbarsha, DNA binding and biological studies of some novel water-soluble polymer-copper(II)-phenanthroline complexes, Eur. J. Med. Chem., 45 (2010) 2082.
  • 23. K. Manjunatha, B. Poojary, P.L. Lobo, J. Fernandes, N.S. Kumari, Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem., 45 (2010) 5225.
  • 24. G.C. Ramaprasad, B. Kalluraya, B.S. Kumar, R.K. Hunnur, Synthesis and biological property of some novel 1,3,4-oxadiazoles, Eur. J. Med. Chem., 45 (2010) 4587.
  • 25. A.A. El-Emam, O.A. Al-Deeb, M. Al-Omar, J. Lehmann, Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4- oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones, Bioorg. Med. Chem., 12 (2004) 5107.
  • 26. 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.
  • 27. 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 (2013a) 125.
  • 28. 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)-a-D-glucopyranoside derivatives, J. Bang. Acad. Sci., 37 (2013b) 145.
  • 29. 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-a-D-glucopyranoside derivatives, J. Bang. Chem. Soc., 25 (2012a) 101.
  • 30. 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 (2012b) 107.
  • 31. 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 (2012c) 66.
  • 32. 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 a-Dglucopyranoside, Pak. J. Sci. Ind. Res., 52 (2009) 138.
  • 33. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S. Rahman, B. Banu, Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidenea-D-glucopyranoside, Chittagong Univ. J. Biol. Sci., 3 (2008) 53.
  • 34. 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.
  • 35. A.K.M.S. Kabir, P. Dutta, M.N. Anwar, Antimicrobial evaluation of some decanoyl derivatives of methyl a-D-glucopyranoside, Int. J. Agric. Biol., 7 (2005b) 760.
  • 36. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S. Rahman, B. Banu, Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidenea-D-glucopyranoside, Chittagong. Univ. J. Sci., 2 (2007) 81.
  • 37. 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.
  • 38. 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.
  • 39. R.K. Grover, J.D. Moore, Toximetric studies of fungicides against the brown rot organisms Sclerotinia flucticola and S. laxa, Phytopathology, 52 (1962) 876.
  • 40. A.K.M.S. Kabir, P. Dutta, M.N. Anwar, Antibacterial and antifungal Evaluation of some Derivatives of methyl a-D-mannopyranoside, Int. J. Agr. Biol., 7 (2005) 756.

Potansiyel Antimikrobiyal Ajanlar Olarak Bazı Yeni D-Glukopiranozit Türevlerinin Sentezi, Tepkimeleri, Spektral Davranışları ve Biyolojik Değerlendirmesi

Yıl 2015, Cilt: 43 Sayı: 4, 309 - 322, 01.11.2015

Öz

B u çalışmada, metil 6-O-sinamoil-α-D-glukopiranozid türevlerinin yeni bir serisi, piridinde çeşitli açilleyici ajanlarla, metil α-D-glukopiranozid 1 tepkimesi ile -5oC’da sentezlendi. Bu amaçla ilk olarak metil α-D-glukopiranosid in seçici sinamalasyonu, doğrudan asilasyon yöntemi ile gerçekleştirildi ve iyi bir verimle metil 6-O-sinamoil-α-D-glukopiranozid elde edildi. İkinci olarak, antimikrobiyal tarama çalışmaları için yeni ürünler elde etmek amacıyla, 6 sinamoil türevleri tek bir molekül çerçevesinde 2,3,4-tri-O-asil türevlerini içeren geniş fonkisyonel gruplara dönüştürüldü. Yeni sentezlenen bileşiklerin yapıları IR ve NMR ile karakterize edildi. Tüm bileşikler, gıda zehirlenmesi ve disk difüzyon yöntemleri kullanılarak in vitro ortamda antibakteriyel ve antifungal aktiviteleri açısından değerlendirildi. Çalışmada metil 6-O-sinamoil-2,3,4-tri-O-dekanoilα-D-glukopiranosid bileşiği hem Gram + B. subtilise hem de Gram - P. aeruginosa mikroorganizmasına karşı yüksek inhibisyon etkisi gösterdi. Test bileşiği, metil 6-O-sinamoil-2,3,4-tri-O-lauroil-α-D-glukopiranosid A ya karşı maksimum misel büyüme inhibisyonu sergiledi. Açillenmiş türevlerin fungal hattına karşı olan etkisinin bakteriyel patojenlere göre daha yüksek olduğu bulundu. Bu, seçilen patojenlere karşı seçilmiş kimyasalların antimikrobiyal etkisini gösteren ilk raporudur

Kaynakça

  • 1. M.E. Taylor, K. Drickamer, Introduction to Glycobiology, Third edition, Oxford University Press, NY, USA (2011).
  • 2. A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, Essentials of Glycobiology, Second edition, Cold Spring Harbor Laboratory Press, Cold Spring, Harbor, NY, USA (2009).
  • 3. J.J. Willard, J.S. Brimacombe, R.P. Brueton, The synthesis of 3-O-[(benzylthio)carbonyl]-β-Dglucopyranose and methyl 2,4,6-tri-O- and β-Dglucopyranosides, Canad. J. Chem., 42 (1964) 2560.
  • 4. 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.
  • 5. R.M. Munavu, H.H. Szmant, Selective formation of 2 esters of some methyl-D-hexopyranosides via dibutylstannylene derivatives, J. Org. Chem., 41 (1976) 1832.
  • 6. H. Ishii, M. Nakamura, S. Seo, K. Tori, T. Tozoyo, Y. Yoshimura, Isolation, characterization and nuclear magnetic spectra of new saponins from the roots of Bupleurum falcatum L, Chem. Pharm. Bull., 28 (1980) 2367.
  • 7. Y. Tsuda, E. Haque, Regioselective introduction of p-coumaroyl group to -L-arabinopyranosides, Total synthesis of inundoside-G and inundoside-D1, Chem. Pharm. Bull., 31 (1983) 1437.
  • 8. 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.
  • 9. D.K. Byarugaba, Antimicrobial resistance in developing countries and responsible risk factors, Int. J. Antimicrob. Agents, 24 (2004) 105.
  • 10. S.J. Projan, D.M. Shlaes, Antibacterial drug discovery: is it all downhill from here, Clin. Microbiol. Infect, 10 (2004) 18.
  • 11. J.J. Barker, Antibacterial drug discovery and structure-based design, Drug Discov. Today, 11 (2006) 391.
  • 12. M.A. Bakht, M.S. Yar, S.G. Abdel-Hamid, S.I. Al Qasoumi, S. Abdul, Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives, Eur. J. Med. Chem., 45 (2010) 5862.
  • 13. R.S. Kumar, A.I. Adhulla, A. J.A. Nasser, J. Selvin, Synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives, J. Seb. Chem. Soc., 76 (2011) 01.
  • 14. H. Singh, K.N. Shukla, R. Dwivedi, L.D.S. Yadav, Cycloaddition of 4-amino-3-mercapto-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.
  • 15. 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-striazolo[3,4-b][1,3,4]thiazolo-6-yl)-indoles, Ind. J. Chem., 36 (1997) 707.
  • 16. M.M. Ghorab, Z.H. Ismail, S.M.A. Gaward, A.A. Aziem, Antimicrobial activity of amino acid, imidazole and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine, Heteroatom Chem., 15 (2004) 57.
  • 17. S.L. Gaonkar, K.M.L. Rai, B. Prabhuswamy, Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5- substituted-1,3,4-oxadiazoles, Eur. J. Med. Chem., 41 (2006) 841.
  • 18. Z.A. Kaplancikli, M.D. Altintop, G. Turan-Zitouni, A. Ozdemir, R. Ozic, G. Akalin, Synthesis, antimicrobial activity and cytotoxicity of novel oxadiazole derivatives, J. Enzyme Inhib. Med. Chem., 27 (2012) 51.
  • 19. Q. Zheng, X. Zhang, X. Ying, K. Cheng, Q. Jiao, H. Zhu, Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents, Bioorg. Med. Chem., 18 (2010) 7836.
  • 20. S. Dash, B.A. Kumar, J. Sing, B.C. Maiti, T.K. Maity, Synthesis of some novel 3,5-disubstituted 1,3,4-oxadiazole derivatives and anticancer activity on EAC animal model, Med. Chem. Res., 20 (2011) 1206.
  • 21. M. A. Ali, M. Shaharyar, Oxadiazole mannich bases: Synthesis and antimycobacterial activity, Bioorg. Med. Chem. Lett., 17 (2007) 3314.
  • 22. R.S. Kumar, S. Arunachalam, V.S. Periasamy, C.P. Preethy, A. Riyasdeen, M.A. Akbarsha, DNA binding and biological studies of some novel water-soluble polymer-copper(II)-phenanthroline complexes, Eur. J. Med. Chem., 45 (2010) 2082.
  • 23. K. Manjunatha, B. Poojary, P.L. Lobo, J. Fernandes, N.S. Kumari, Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem., 45 (2010) 5225.
  • 24. G.C. Ramaprasad, B. Kalluraya, B.S. Kumar, R.K. Hunnur, Synthesis and biological property of some novel 1,3,4-oxadiazoles, Eur. J. Med. Chem., 45 (2010) 4587.
  • 25. A.A. El-Emam, O.A. Al-Deeb, M. Al-Omar, J. Lehmann, Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4- oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones, Bioorg. Med. Chem., 12 (2004) 5107.
  • 26. 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.
  • 27. 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 (2013a) 125.
  • 28. 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)-a-D-glucopyranoside derivatives, J. Bang. Acad. Sci., 37 (2013b) 145.
  • 29. 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-a-D-glucopyranoside derivatives, J. Bang. Chem. Soc., 25 (2012a) 101.
  • 30. 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 (2012b) 107.
  • 31. 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 (2012c) 66.
  • 32. 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 a-Dglucopyranoside, Pak. J. Sci. Ind. Res., 52 (2009) 138.
  • 33. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S. Rahman, B. Banu, Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidenea-D-glucopyranoside, Chittagong Univ. J. Biol. Sci., 3 (2008) 53.
  • 34. 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.
  • 35. A.K.M.S. Kabir, P. Dutta, M.N. Anwar, Antimicrobial evaluation of some decanoyl derivatives of methyl a-D-glucopyranoside, Int. J. Agric. Biol., 7 (2005b) 760.
  • 36. A.K.M.S. Kabir, S.M.A. Kawsar, M.M.R. Bhuiyan, M.S. Rahman, B. Banu, Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidenea-D-glucopyranoside, Chittagong. Univ. J. Sci., 2 (2007) 81.
  • 37. 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.
  • 38. 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.
  • 39. R.K. Grover, J.D. Moore, Toximetric studies of fungicides against the brown rot organisms Sclerotinia flucticola and S. laxa, Phytopathology, 52 (1962) 876.
  • 40. A.K.M.S. Kabir, P. Dutta, M.N. Anwar, Antibacterial and antifungal Evaluation of some Derivatives of methyl a-D-mannopyranoside, Int. J. Agr. Biol., 7 (2005) 756.
Toplam 40 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Article
Yazarlar

Sarkar Mohammad Abe Kawsar Bu kişi benim

Refat Asma Bu kişi benim

Khaleda Mymona Bu kişi benim

Mohammad Abul Manchur Bu kişi benim

Imtiaj Hasan Bu kişi benim

Yasuhiro Ozeki Bu kişi benim

Yayımlanma Tarihi 1 Kasım 2015
Yayımlandığı Sayı Yıl 2015 Cilt: 43 Sayı: 4

Kaynak Göster

APA Kawsar, S. M. A., Asma, R., Mymona, K., Manchur, M. A., vd. (2015). Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents. Hacettepe Journal of Biology and Chemistry, 43(4), 309-322.
AMA Kawsar SMA, Asma R, Mymona K, Manchur MA, Hasan I, Ozeki Y. Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents. HJBC. Kasım 2015;43(4):309-322.
Chicago Kawsar, Sarkar Mohammad Abe, Refat Asma, Khaleda Mymona, Mohammad Abul Manchur, Imtiaj Hasan, ve Yasuhiro Ozeki. “Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives As Potential Antimicrobial Agents”. Hacettepe Journal of Biology and Chemistry 43, sy. 4 (Kasım 2015): 309-22.
EndNote Kawsar SMA, Asma R, Mymona K, Manchur MA, Hasan I, Ozeki Y (01 Kasım 2015) Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents. Hacettepe Journal of Biology and Chemistry 43 4 309–322.
IEEE S. M. A. Kawsar, R. Asma, K. Mymona, M. A. Manchur, I. Hasan, ve Y. Ozeki, “Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents”, HJBC, c. 43, sy. 4, ss. 309–322, 2015.
ISNAD Kawsar, Sarkar Mohammad Abe vd. “Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives As Potential Antimicrobial Agents”. Hacettepe Journal of Biology and Chemistry 43/4 (Kasım 2015), 309-322.
JAMA Kawsar SMA, Asma R, Mymona K, Manchur MA, Hasan I, Ozeki Y. Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents. HJBC. 2015;43:309–322.
MLA Kawsar, Sarkar Mohammad Abe vd. “Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives As Potential Antimicrobial Agents”. Hacettepe Journal of Biology and Chemistry, c. 43, sy. 4, 2015, ss. 309-22.
Vancouver Kawsar SMA, Asma R, Mymona K, Manchur MA, Hasan I, Ozeki Y. Synthesis, Reactions, Spectral Behavior and Biological Evaluation of Some New D-Glucopyranoside Derivatives as Potential Antimicrobial Agents. HJBC. 2015;43(4):309-22.

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