ABSTRACT.This study was carried out to regioselective myristoylation of methyl α-Dglucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-Omyristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1 H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

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-5 o C'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-triO -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-triO -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-triO -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.

This study was carried out to regioselective myristoylation of methyl α-D-glucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-O-myristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.