146579-19-3

Upstream product

• 362-42-5 2',3'-O-isopropylidenecytidine 

Downstream Products

• 1174010-26-4 C₄₇H₅₉N₁₉O₁₃ 
• 1174010-32-2 C₃₇H₅₇N₁₉O₁₃ 
• 1174010-38-8 C₄₅H₆₅N₂₁O₁₄S 

Relevant academic research and scientific papers

Parallel Solution Phase Synthesis and Preliminary Biological Activity of a 5′-Substituted Cytidine Analog Library

A 109-membered library of 5′-substituted cytidine analogs was synthesized, via funding through the NIH Roadmap Initiative and the Pilot Scale Library (PSL) Program. Reaction core compounds contained -NH2 (2) and -COOH (44 and 93) groups that were coupled to a diversity of reactants in a parallel, solution phase format to produce the target library. The assorted reactants included -NH2, -CHO, -SO2Cl, and -COOH functional groups, and condensation with the intermediate core materials 2 and 44 followed by acidic hydrolysis produced 3-91 in good yields and high purity. Linkage of the amino terminus of d-phenylalanine methyl ester to the free 5′-COOH of 44 and NaOH treatment led to core library -COOH precursor 93. In a libraries from libraries approach, compound 93 served as the vital building block for our unique library of dipeptidyl cytidine analogs 94-114 through amide coupling of the -COOH group with numerous commercial amines followed by acidic deprotection. Initial screening of the complete final library through the MLPCN program revealed a modest number of hits over diverse biological processes. These hits might be considered as starting points for hit-to-lead optimization and development studies.

Synthesis and biological evaluation of novel neamine-nucleoside conjugates potentially targeting to RNAs

Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs.

Ruthenium tetraoxide catalyzed oxidation of nucleosides: A facile synthesis of 5'-carboxylic acid derivatives

Purine and pyrimidine nucleosides have been oxidized to the corresponding 5'-carboxylic acids using potassium persulfate and ruthenium trichloride under basic conditions. The method provides easy access to nucleosides bearing 3'-amino and 5'-carboxylic acid functionalities from 3'-azido compounds as exemplified by oxidation of AZT followed by reduction of the acid.