Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity

Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity Full article

Journal

ACS Combinatorial Science
ISSN: 2156-8952 , E-ISSN: 2156-8944

Output data

Year: 2012, Volume: 14, Number: 8, Pages: 484-490 Pages count : 7 DOI: 10.1021/co300062e

Authors

Shestopalov Anatoliy M. ¹ , Litvinov Yuri M. ¹ , Rodinovskaya Lyudmila A. ¹ , Malyshev Oleg R. ¹ , Semenova Marina N. ² , Semenov Victor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, RAS, 47 Leninsky Prospect,#R#119991 Moscow, Russian Federation
2	N. K. Koltzov Institute of Developmental Biology, RAS, 26 Vavilov Street, 119334,#R#Moscow, Russian Federation

A series of 4H-chromenes containing various modifications in the ring B and polyalkoxy substituents in the ring E has been synthesized by Knoevenagel–Michael–hetero-Thorpe–Ziegler three-component domino reaction with the overall yield of 45–82%. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antimitotic and microtubule destabilizing activity. The most active compounds 5{1,5} and 5{5,5} featured sesamol-derived ring B and m-methoxyphenyl or m-methoxymethylenedioxyphenyl ring E. Compounds 5{3,1}, 5{1,2}, 5{5,4}, 5{1,5}, and 5{5,5} exhibited strong cytotoxicity in the NCI60 human tumor cell line anticancer drug screen. Surprisingly, cell growth inhibition caused by these agents was more pronounced in the multidrug resistant NCI/ADR-RES cells than the parent OVCAR-8 cell line. The results suggest that polyalkoxy substited 4H-chromenes may prove to be advantageous for further design as anticancer agents.

Shestopalov A.M. , Litvinov Y.M. , Rodinovskaya L.A. , Malyshev O.R. , Semenova M.N. , Semenov V.V.
Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity
ACS Combinatorial Science. 2012. V.14. N8. P.484-490. DOI: 10.1021/co300062e WOS Scopus OpenAlex

Web of science:	WOS:000307422000008
Scopus:	2-s2.0-84865021356
OpenAlex:	W2321885193

DB	Citing
OpenAlex	105
Scopus	112
Web of science	106