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Synthesis and Anti‐HIV Activity of Triazolo‐Fused, Medium‐Sized Cyclic Nucleoside Analogs Prepared by an Intramolecular Huisgen 1,3‐Dipolar Cycloaddition
Author(s) -
Sun Jingbo,
Liu Rongwang,
Fu Qiang,
Zang Jian,
Tao Qiangqiang,
Wu Jinchang,
Zhu Hui
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300289
Subject(s) - chemistry , cycloaddition , intramolecular force , uracil , nucleoside , 1,3 dipolar cycloaddition , click chemistry , ring (chemistry) , triazole , cytosine , toluene , combinatorial chemistry , stereochemistry , organic chemistry , dna , catalysis , biochemistry
Medium‐sized cyclic nucleosides containing a fused triazole ring were synthesized via intramolecular Huisgen 1,3‐dipolar cycloadditon reaction. 2′,3′‐ seco‐ Uridine was employed as the key intermediate for the introduction of azido and alkynyl moieties in the defined positions of the reaction precursors. The cycloaddition reactions were achieved in high yields by heating the precursor in refluxing toluene. The uracil base in these target compounds was successfully transformed to the corresponding cytosine. The synthesized compounds were evaluated in a MAGI assay for their anti‐HIV activities, and in a H9 T lymphocytes assay for their cell toxicities.