Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

Abstract

Abstract. An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1′-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1′,N-3′-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5′-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5′-ethynyl derivative which was further transformed into 5′-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5′-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.

Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis

“…Indeed, despite their attractive biological properties, 11 few synthetic efforts have been carried out in this regard. 12 Other approaches toward the synthesis of “reverse aryl C- glycosides” have been reported, such as the [4+2] cycloaddition between Danishefsky’s dienes and aromatic aldehydes, yielding glycal derivatives, 13 or the addition of organozinc reagents to 4α-epoxypyranosides (Scheme 2).…”

“…In this context, the development of straightforward, modular, and operationally simple conditions to access C -arylated saccharides remains an unsolved challenge and, specifically, methods that would preserve the anomeric carbon to afford non-classical “reverse aryl C -glycosides” are particularly scarce. Indeed, despite their attractive biological properties, 11 few synthetic efforts have been carried out in this regard. 12 Other approaches toward the synthesis of “reverse aryl C- glycosides” have been reported, such as the [4+2] cycloaddition between Danishefsky’s dienes and aromatic aldehydes, yielding glycal derivatives, 13 or the addition of organozinc reagents to 4α-epoxypyranosides (Scheme 2).…”

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

“…[24][25][26][27][28][29] Our group has a long-term experience in design, synthesis, and characterization of biologically active nucleoside derivatives. [30][31][32][33] Previously, we have synthesized N-sulfonylpyrimidine derivatives I (Figure 2) as a new type of sulfonylcycloureas. [34][35][36][37] These compounds showed strong antiproliferative activity on human tumor cell lines, in in vitro [38][39][40][41] and in vivo [42][43][44][45] conditions.…”

Synthesis of some New Dihydropyrimidines Derivatives by Cyclization of Polarized Unsaturated Systems

“…Nitrogen containing heterocyclic compounds constitutes the largest portion of chemical entities, which are part of many natural biologically active pharmaceuticals, which are vital for enhancing quality of life . Pyrimidines, as the most important nitrogen‐containing heterocyclic compounds, are of chemical and pharmacological interest.…”