152963-76-3Relevant academic research and scientific papers
Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs
Troup, Robert I.,Jeffries, Benjamin,Saudain, Raphael El-Bekri,Georgiou, Eleni,Fish, Johanna,Scott, James S.,Chiarparin, Elisabetta,Fallan, Charlene,Linclau, Bruno
, p. 1882 - 1900 (2021/02/03)
Given there is an optimal lipophilicity range for orally bioavailable drugs, structural modifications applied in the drug development process are not only focused on optimizing bioactivity but also on fine-tuning lipophilicity. Fluorine introduction can b
NUCLEOTIDE AND NUCLEOSIDE COMPOSITIONS AND USES RELATED THERETO
-
Page/Page column 195; 196, (2015/03/28)
This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.
NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO
-
Page/Page column 145, (2014/08/20)
This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to halogenated nucleosides optionally conjugated to a phosphorus oxide or pharmaceutically acceptable salts thereof. In certain embodiments, the disclosure relates to conjugate compounds or pharmaceutically acceptable salts thereof comprising an amino acid ester or a sphingolipid or derivative linked by a phosphorus oxide to a nucleotide or nucleoside. In certain embodiments, the disclosure contemplates pharmaceutical compositions comprising these compounds for uses in treating infectious diseases, viral infections, and cancer.
Novel Bicyclic Pyridinones
-
, (2014/04/03)
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
A Completely Diastereoselective Electrophilic Fluorination of a Chiral, Noncarbohydrate Sugar Ring Precursor: Application to the Synthesis of Several Novel 2′-Fluoronucleosides
Jeffrey McAtee,Schinazi, Raymond F.,Liotta, Dennis C.
, p. 2161 - 2167 (2007/10/03)
A new and completely diastereoselective method for the introduction of fluorine into a noncarbohydrate sugar ring precursor has been developed. The use of N-fluorodibenzenesulfonimide (5) for the electrophilic fluorination of chiral lactone 4, which is derived from L-glutamic acid, yields the key intermediate 6. This is transformed into an anomeric acetate 8 and is used for the synthesis of a number of novel α-2′-fluoronucleosides. Since glutamic acid is used as the synthetic starting material, the L enantiomer may also be synthesized simply by using D-glutamic acid. The incorporation of fluorine into the 2′ position of the nucleoside provides several advantages including acid stability of the anomeric bond and general resistance to oxidative metabolism. Further, fluorine is a close mimic of hydroxyl groups in size and polarity and in its ability to act as a hydrogen bond acceptor. This may aid in the recognition of these nucleosides by the enzymes involved in nucleoside activation.
Synthesis of 2-fluoro sugar and its condensation reaction with silylated thymine
Niihata,Ebata,Kawakami,Matsushita
, p. 1509 - 1512 (2007/10/02)
2,3-Dideoxy-2-fluoro-D-erythro-pentofuranose was easily prepared from 3-DPA lactone. The condensation reaction between 1-O-acetyl derivative of this sugar and silylated thymine in the presence of TMSOTf proceeded in a poorly stereoselective manner.
