Abstract
This paper includes the synthesis of some new nucleoside analogues starting with 2-substituted benzimidazole derivative (7-9), that synthesized by condensation of O-phenylenediamine with p-chloro benzaldehyde and two substituted benzoic acid , which on nucleophilic substitution with propargyl bromide gave a new N-substituted compounds (10-12). D-Fructose and D-galactose were chosen as a sugar moiety which were protected, brominated and azotated to give azido sugars (5) and (6), then they were subjected to 1,3-dipolar cycloaddition reaction with N-substuted compounds afforded bloked nucleoside analoges (13-16), which after hydrolysis gave our target the free nucleoside analogues (17-20). All prepared compounds were identified by FT-IR and some of them with 1H-NMR and 13C-NMR.
Highlights
In recent years Nucleoside analogues played pivotal roles in the treatment of viral infections and cancer, nucleosides are active ingredient of one third of the antiviral drugs approved by the US food and drug administration (FDA)[1], considered one of the great importance among the compounds with antiviral activity; to modulate nucleoside or nucleotide activity, the strategy has been modified one of the three major subunit moiety[2]
General procedure Synthesis of 1,3,4,6- tetra –O-benzoyl –β-D- fructofuranose Benzoyl chloride ( 14 ml ) was added to anhydrous –D- fructose ( 4 g, 22.22 mmol) that suspended in a mixture of chloroform (60 ml) and dry pyridine (10 ml), the mixture was heated on water bath at ( 45-65) ̊C with continuous stirring for 4 hs
Modified nucleosides represent an important class of medicinal compounds which have been found to behave as therapeutic agents and are currently used in pharmaceuticals as antitumor, antiviral and antibiotic agent.( 16) Physical properties of sugars compounds (2-6) were agreed with that in the literature The FT-IR spectrum for compound (2) showed stretching band at 3064cm-1(CH arom.), 2929cm-1(C-H aliph.), a stretching band at 1710 cm-1(C=O benzoate), 1573 cm-1(C=C)arom., and 659.61 cm-1(C-Br), while a stretching broad band of the hydroxyl group was disappeared(Table 1)
Summary
In recent years Nucleoside analogues played pivotal roles in the treatment of viral infections and cancer, nucleosides are active ingredient of one third of the antiviral drugs approved by the US food and drug administration (FDA)[1], considered one of the great importance among the compounds with antiviral activity; to modulate nucleoside or nucleotide activity, the strategy has been modified one of the three major subunit moiety[2] Nucleoside analogues such as Favipiravir, has demonstrated success in treating Ebola virus infections in both cell culture and small animal models [3,4]. New antiviral drugs and in last year's several biological application like antimicrobial[7], antiviral especially HIV virus[8], antiprotozoal[9], antiinflammatory[10], anthelmintic[11], antihypertensive[12], anti-tumor[13] and anticonvulsant activities[14] and CNSdepressant[15],have been reported for benzimidazole derivatives[16]
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