SYNTHESIS OF 5-Chloro-1-(2,3-Dideoxy-3-Fluoro-Β-D-Glycero-Hex-2-Enopyranose-4-Ulosyl)uracil AS POTENTIAL ANTICANCER/ANTIVIRAL AGENT

Abstract

Peracetylated alpha-D-glucose was coupled with silylated 5-chlorouracil. The product (2) was deacetylated and 4',6'-hydroxyls were then protected with 4',6'-O-isopropylidene group. Fluorine was introduced at the 3'-position, followed by acetylation, deprotection, tritylation, oxidation and deritylation of subsequent compounds gave the target compound (10).

The σ‐Hole Phenomenon of Halogen Atoms Forms the Structural Basis of the Strong Inhibitory Potency of C5 Halogen Substituted Glucopyranosyl Nucleosides towards Glycogen Phosphorylase b

“…Chemical and physical properties of nucleosides 2 a , 2 b , and 2 c are in agreement with previously reported data 46. 47…”

Simulation of a tetramer form of 5-chlorouracil: The vibrational spectra and molecular structure in the isolated and in the solid state by using DFT calculations

“…Some of their derivatives such as 6-amino-5-ClU [19,20], 5-chloro-6-[1-(2-iminopyrrolidinyl)methyl] uracil [21], or 6-(2-aminoethyl)amino-5-chlorouracil [22], are the most potent human thymidine phosphorylase inhibitors. Other derivatives [23] are potential anticancer/antiviral agents.…”

Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity

“…[12,13] In recent years, pyranosyl nucleosides are viewed as important modifications of natural nucleosides, offering promising avenues in the development of novel bioactive agents with promising therapeutic potential. [14][15][16][17][18][19][20][21][22][23][24] In our previous investigations, we demonstrated that base-modified pyranonucleosides rank among the most potent glycogen phosphorylase (GP) [25,26] and thymidylate synthase (TS) [27] inhibitors, and were endowed with a pronounced cytostatic and antiviral action. [28] As a continuation of this research and based on the pharmacological properties of thiopurine analogues, we now report the synthesis and biology of new thiopurine pyranonucleosides via glycosylation of mercaptopurine and thioguanine pyranonucleosides bearing D-glucose, D-galactose, D-xylose, D-mannose, and D-lyxose as sugar moiety.…”