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Synthesis and cytotoxic evaluation of apioarabinofuranosyl pyrimidines
Author(s) -
Sivakrishna Balija,
Islam Sehbanul,
Santra Manas K.,
Pal Shantanu
Publication year - 2020
Publication title -
drug development research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.582
H-Index - 60
eISSN - 1098-2299
pISSN - 0272-4391
DOI - 10.1002/ddr.21613
Subject(s) - pyrimidine , uracil , chemistry , nucleoside , nucleobase , stereochemistry , cytosine , combinatorial chemistry , biochemistry , dna
In view of the potent anticancer activity of the d ‐arabino‐configured cytosine nucleoside (ara‐C), apioarabinofuranosyl pyrimidine nucleosides were designed and synthesized from d ‐ribose as starting material. The synthetic strategy signifies that tosylation followed by in situ cyclization, one‐pot controlled oxidative cleavage and acetylation by Pb(OAc) 4 , stereoselective nucleobase condensation, inversion of hydroxyl group and uracil group converted to cytosine as the key steps. Synthesized apioarabinofuranosyl pyrimidine nucleosides were tested using breast, colon, and ovarian cancer cell lines. However, only compound 19a , 19b, and 22b have a moderate growth‐suppressive effect against the luminal A breast cancer cell line MCF7.