ChemInform Abstract: Synthesis and Biological Activities of Novel s‐Triazine Bridged Dinucleoside Analogues.

Shen, Fang‐Fang; Yin, Qingmei; Chen, Hua; Zhang, Xiaoyuan; Li, Xiaoliu; Qin, Zhanbin; Zhang, Jinchao

doi:10.1002/chin.201146192

Cited by 1 publication

(1 citation statement)

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“…5′-Amino and 5′-carboxylic nucleosides are common staring points to prepare diverse nucleosides for screening. − Consequently, the nucleoside 2 and nucleosides 44 and 93 were chosen as three diversification reagents for robust reductive aminations, sulfonation reactions, or amidations in order to synthesize our unique cytidine-based library as depicted in Schemes –.…”

Section: Experimental Design and Discussionmentioning

confidence: 99%

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

et al. 2019

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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.

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