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Synthesis and in vitro study of antiproliferative benzyloxy dihydropyrimidinones
Author(s) -
Vala Ruturajsinh M.,
Sharma Mayank G.,
Patel Divyang M.,
Puerta Adrián,
Padrón José M.,
Ramkumar Venkatachalam,
Gardas Ramesh L.,
Patel Hitendra M.
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000466
Subject(s) - chemistry , trifluoromethanesulfonate , biginelli reaction , in vitro , urea , combinatorial chemistry , cell culture , yield (engineering) , stereochemistry , organic chemistry , biochemistry , catalysis , materials science , biology , metallurgy , genetics
In this study, we report on antiproliferative benzyloxy dihydropyrimidinones (DHPMs) produced by the Biginelli reaction of benzyloxy benzaldehyde, urea, and diverse 1,3‐diones. The reaction was catalyzed by lanthanum triflate and completed within 1–1.5 h, with 74–97% yield. The antiproliferative assay was carried out for all synthesized dihydropyrimidinones against six human solid tumor cell lines. Six compounds showed good antiproliferative activity with GI 50 values below 5 μM. Among all the synthesized compounds, the most potent derivative showed good antiproliferative activity against all cell lines with GI 50 values in the range of 1.1–3.1 μM. These DHPMs comply with druglikeness. Furthermore, ADMET prediction and the effect of P‐glycoprotein on the antiproliferative activity were also studied. Overall, our method allows eco‐friendly access to benzyloxy DHPMs as potential anticancer drugs.