Journal
NATURAL PRODUCT RESEARCH
Volume 35, Issue 1, Pages 9-16Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2019.1610958
Keywords
Podophyllotoxin; click chemistry; Ag (NHC) catalyst; podophyllotoxin-glycosyl triazoles; anticancer studies
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Funding
- University Grants Commission, Government of India [UGC-MRP-5732/15/620]
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This study reports the regioselective synthesis of podophyllotoxin-glycosyl triazole hybrids catalyzed by Ag(I)-NHC, showing promising anticancer activity against four human cancer cell lines. Compounds 5a and 5e were identified as potential leads due to their superior activity compared to the standard drug etoposide across all cell lines. Molecular docking studies revealed good agreement between the free energy calculations of active compounds and observed IC50 values.
Herein we report the regioselective synthesis of podophyllotoxin-Glycosyl triazole hybrids catalysed by Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) in a short reaction time (similar to 30 min) at ambient conditions. In principle, it is the first report of Click alkyne-azide cycloaddition catalysed by Ag(I)-NHC catalyst and moreover, this new methodology yielded good results when compared with traditional CuAAC in terms of reaction time and selectivity. The synthesised compounds were further explored for in vitro anticancer activity against four human cancer cell lines Du145, HeLa, A-549, and MCF-7 and found that these synthesised compounds possess significant anticancer activity. Further, the compounds 5a and 5e were identified as promising leads due to their better activity across all cell lines than that of the standard drug etoposide. Molecular docking studies of 5a & 5e with DNA Topoisomerase-II were revealed that the free energy calculations of active compounds were in good agreement with observed IC50 values. [GRAPHICS] .
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