Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides
نویسندگان
چکیده
The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′(α)-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′(α)-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs’ catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.
منابع مشابه
TETRA-N-BUTYLAMMONIUM FLUORIDE AS A NOVEL REAGENT FOR THE PREPARATION OF ACYCLO-NUCLEOSIDES. THE SYNTHESIS OF 9- [(2-HYDROXYETHOXY) METHYL] ADENINE, BITAMYCIN.
The synthesis of the title compound, bitamycin, by means of BU4NF is described. This new antiviral drug was found to be one of the most powerful and least toxic substances for antiviral therapy in man. The physical and chemical behavior as well as the antiviral activities and clinical properties of this compound were found to be significantly different from that reported by Schaeffer, et a...
متن کاملCarbocyclic analogues of nucleosides from bis-(Hydroxymethyl)-cyclopentane: synthesis, antiviral and cytostatic activities of adenosine, inosine and uridine analogues.
Six new carbocyclic nucleosides were prepared by constructing a purine base (in compounds 9-11) or pyrimidine base (in 6-8) on the amino groups of (+/-)-(1 beta,2 alpha,4 beta)-4-amino-1,2-cyclopentanedimethanol (4) and (+/-)-(1 beta,3 alpha,4 beta)-4-amino-1,3-cyclopentanedimethanol (5), and their activities against a variety of viruses and tumour cell lines were determined.
متن کاملSynthesis of a novel carbocyclic analog of bredinin.
The natural nucleoside antibiotic, bredinin, exhibits antiviral and other biological activities. While various nucleosides related to bredinin have been synthesized, its carbocyclic analog has remained unknown. Synthesis of this heretofore unknown analog of bredinin is described. The key precursor, (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4...
متن کاملStereocontrolled synthesis of carbocyclic compounds with a quaternary carbon atom based on SN2' alkylation of γ,δ-epoxy-α,β-unsaturated ketones.
We developed a new method for stereoselective construction of an all-carbon quaternary stereogenic center on a carbocyclic ring based on regio- and stereoselective S(N)2' alkylation reactions of γ,δ-epoxy-α,β-unsaturated cyclic ketones. Treatment of the ketones, which were readily prepared in enantiomerically pure form by means of aldol condensations between 3-ethoxy-2-cycloalkenones and α,β-ep...
متن کاملSynthesis, characterization and polymerization of a novel acrylate monomer containing both 4H-pyran-4-one and 1,2,3-triazole moiety and evaluation of their antibacterial activity
A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis ...
متن کامل