We describe the synthesis, structure and DNA incorporation of a class of novel aromatic C-deoxynucleosides in which benzenes and larger polycyclic aromatics serve as DNA base analogs. Novel approaches have been developed for glycosidic bond formation and for epimenzation of the anomeric substitutents to β-configuration, and we describe some of the properties of such compounds in DNA.
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http://dx.doi.org/10.1055/s-1997-788 | DOI Listing |
J Org Chem
December 2024
Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
The synthesis of 1-azido -nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1-azidation with complete β-diastereoselectivity.
View Article and Find Full Text PDFArch Pharm (Weinheim)
March 2024
Biocatalysis and Organic Synthesis Group, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil.
In the last 50 years, nucleoside analogs have been introduced to drug therapy as antivirals for different types of cancer due to their interference in cellular proliferation. Among the first line of nucleoside treatment drugs, ribavirin (RBV) is a synthetic N-nucleoside with a 1,2,4-triazole moiety that acts as a broad-spectrum antiviral. It is on the World Health Organization (WHO) list of essential medicines.
View Article and Find Full Text PDFArch Pharm (Weinheim)
January 2024
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, Egypt.
Breast cancer continues to be the most frequent cancer worldwide. In practice, successful clinical outcomes were achieved via targeting DNA. Along with the advances in introducing new DNA-targeting agents, the "sugar approach" design was employed herein to develop new intercalators bearing pharmacophoric motifs tethered to carbohydrate appendages.
View Article and Find Full Text PDFNucleosides Nucleotides Nucleic Acids
November 2023
Nature Pharmaceutical (Anhui) Co., Ltd, Anqing, P. R. China.
Nucleoside analogues are prevalent in drug design and call for more diversified structures. Bicyclo[1.1.
View Article and Find Full Text PDFMolecules
December 2022
Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovského nám. 2, 162 06 Prague, Czech Republic.
A highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(d-glycosyloxy) phthalazine nucleosides ,, , -nucleosides , , , and acyclo nucleosides ,, , and - was described and fully characterized. Furthermore, a series of desired new nucleoside analogues containing Se of 4-(pyren-1-ylmethyl) phthalazine-1(2)-selenone - were synthesized. The structures of all reported compounds were confirmed by IR, H-NMR, C-NMR, MS and elemental analysis.
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