Design and Newly Synthesis of some 1,2-O-Isopropylidene-α-D-Glucofuranose Derivatives: Characterization and Antibacterial Screening Studies

Year 2013, Volume: 41 Issue: 3, 195 - 206, 01.09.2013

Sarkar Mohammad Abe Kawsar Md Moinul Islam Shagir Ahammad Chowdhury Tanvirul Hasan Mohammed Kamrul Hossain Mohammad Abul Manchur Yasuhiro Ozeki

Abstract

D-Glucose was converted into the 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 1 in good yield. Removal of 5,6-O-isopropylidene group from diacetone glucose 1 was achieved by careful hydrolysis which provided the monoacetal glucose 2 . Here we reported the selective acylation of 1,2-O-isopropylidene-α- D-glucofuranose 2 by the direct method using a number of acylating agents furnished the corresponding 3,5,6-tri-O-acyl derivatives in reasonable yields. The structures of the newly synthesized compounds were ascertained by FTIR, 1H-NMR spectroscopy and elemental analysis. All the synthesized compounds were employed as test chemicals for in vitro antibacterial functionality test against six human pathogenic bacteria. The evaluation study revealed that the tested chemicals exhibited moderate to good antibacterial activities. It was also observed that the test chemicals were more effective against Gram-positive bacteria than that of the Gram-negative microorganisms.

Keywords

D-Glucose, acylation, spectroscopy, antibacterial

Bazı 1,2-O-izopropiliden-α-D-Glucofuranose Türevlerinin Tasarım ve Yeni Sentez Metodu: Karakterizasyonu ve Antibakteriyel Tarama Çalışmaları

Abstract

D -glukoz, iyi bir verimle 1,2:5,6-di-O-izopropiliden-α-D-gluko furanoz 1 dönüştürüldü. Diaseton glikoz 1 ’dan 5,6-O-izopropiliden grubunun çıkarılması, mono asetal glikoz 2 ’un elde edilmesini sağlayarak, dikkatli bir şekilde hidroliz ile elde edilmiştir. Burada karşılık gelen 3,5,6-tri-O-asil türevlerinin döşenmiş asile edici bir dizi ajan kullanarak uygun verimle doğrudan 1,2-O-izopropiliden-α-D-gluckofuranoz 2 ‘nin seçici asilasyonu rapor edilmektedir. Yeni sentezlenmiş bileşiklerin yapıları FTIR, 1H-NMR spektroskopisi ve element analizi ile tespit edildi. Sentezlenen tüm bileşikler altı insan patojen bakterisine karşı in vitro antibakteriyel işlevsellik test kimyasalı olarak kullanılmıştır. Değerlendirme çalışması, test kimyasalları iyi antibakteriyel işlevlerine orta derecede tepki verdiğini göstermiştir. Aynı zamanda, test kimyasallarının, Gram-pozitif bakterilere karşı Gramnegatif mikroorganizmalara olduğundan daha etkili olduğu görülmüştür

Keywords

D-Glikoz, asilasyon, spektroskopi, antibakteriyel

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