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

Year 2015, Volume: 43 Issue: 4, 309 - 322, 01.11.2015

Sarkar Mohammad Abe Kawsar Refat Asma Khaleda Mymona Mohammad Abul Manchur Imtiaj Hasan Yasuhiro Ozeki

Abstract

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.

Keywords

D-Glucopyranoside, acylation, structure, spectroscopy, antibacterial, antifungal

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

Abstract

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

Keywords

D-glukopiranozid, açilasyon, yapı, spektroskopi, antibakteriyel, antifungal

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