Synthesis, characterization and biological evaluation of purine nucleoside analogues

[Display omitted] •Deals with the easy synthesis of purine nucleoside based derivatives.•In vitro anticancer efficacy of the synthesized analogues.•Some of the compounds have been emerged as promising candidates. We present a convenient route for the synthesis of C6-amino-C5′-N-cyclopropyl carboxami...

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Bibliographic Details
Published in:Tetrahedron letters 2017-11, Vol.58 (44), p.4166-4168
Main Authors: Malthum, Shankaraiah, Polkam, Naveen, Allaka, Tejeswara Rao, Chepuri, Kalyani, Anireddy, Jaya Shree
Format: Article
Language:English
Subjects:
Cytotoxicity
Doxorubicin
Purine nucleosides
Sonogashira coupling
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Summary:[Display omitted] •Deals with the easy synthesis of purine nucleoside based derivatives.•In vitro anticancer efficacy of the synthesized analogues.•Some of the compounds have been emerged as promising candidates. We present a convenient route for the synthesis of C6-amino-C5′-N-cyclopropyl carboxamido-C2-alkynylated purine nucleoside analogues 11a–g via Sonogashira coupling reaction. The nine step synthesis is easy to perform, employing commercially available reagents. Compound 9 is used as key intermediate for the synthesis of analogues 11a–g. Synthetic intermediates and final products are appropriately characterized by IR, 1H NMR, 13C NMR and Mass. The modified nucleoside analogues 11a–g is evaluated for in vitro anticancer activity against MDA-MB-231 and Caco-2 cell lines. Screening data reveals that compounds 11b and 11e displayed potent IC50 value of 7.9, 6.8µg/mL respectively against MDA-MB-231 and of 7.5, 8.3µg/mL respectively against Caco-2 than the standard drug doxorubicin, thus establishing the potential anti-cancer properties of these newer derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.09.041