Synthesis and Cytotoxicity of 6-Selenopurine Arabinoside and Related Compounds

Chu, Shih–Hsi; Shiue, Chyng‐Yann; Chu, Ming

doi:10.1002/jps.2600640818

Cited by 4 publications

(1 citation statement)

References 25 publications

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“…Simple selanylpurine analogs, similarly to 6-thioguanine, have been tested for leukemia treatment and as immunosuppressants, but their selectivity and cytotoxicity levels had to be optimized. − This issue was partially overcome by selenoguanine-platinum(II) and selenopurine and selenoguanine ruthenium complexes. , These complexes were more stable and less toxic but had reduced anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 6-Selanyl-2-triazolylpurine Derivatives Using 2,6-Bistriazolylpurines as Starting Materials

Ritere,

Jeminejs,

Bizde̅na

et al. 2024

ACS Omega

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Two pathways toward 6-selanyl-2-triazolylpurine derivatives were designed. The first method involved the synthesis of 2-chloro-6-selanylpurine derivatives, further S N Ar reaction with NaN 3 , and following CuAAC using different alkynes. The second method was based on the synthesis of 2,6-bistriazolylpurine derivatives as starting materials followed by S N Ar reaction with commercial or in situ generated selenols as nucleophiles. A series of 2-chloro-6-selanylpurine derivatives were obtained in yields up to 84%. It was found that in the latter compounds, 6-selanyl moiety was the better leaving group compared to 2-chlorosubstituent in S N Ar reactions. On the other hand, the S N Ar reaction between 2,6-bistriazolylpurines and selenols or diselenides was successful, and 13 examples of 6-selanyl-2-triazolylpurine derivatives were obtained in yields up to 87%. This direct approach for the Se−C bond formation proved the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as a good leaving group.

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