Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents

Evgeniy A. Gusakov; Iuliia A. Topchu; Aleksandra M. Mazitova; Igor V. Dorogan; Emil R. Bulatov; Ilya G. Serebriiskii; Zinaida I. Abramova; Inna O. Tupaeva; Oleg P. Demidov; Duong Ngoc Toan; Tran Dai Lam; Duong Nghia Bang; Yanis A. Boumber; Yurii A. Sayapin; Vladimir I. Minkin

doi:10.1039/D0RA10610K

Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents†

Evgeniy A. Gusakov,‡^a Iuliia A. Topchu,‡^bc Aleksandra M. Mazitova,‡^bd Igor V. Dorogan,

^a Emil R. Bulatov,^b Ilya G. Serebriiskii,^be Zinaida I. Abramova,

^b Inna O. Tupaeva,^a Oleg P. Demidov,

^f Duong Ngoc Toan,^g Tran Dai Lam,^h Duong Nghia Bang,ⁱ Yanis A. Boumber,*^bc Yurii A. Sayapin

*^j and Vladimir I. Minkin

^a

Author affiliations

* Corresponding authors

^a Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russia

^b Kazan Federal University, Kazan, Russia

^c Robert H Lurie Comprehensive Cancer Center, Division of Hematology/Oncology at the Department of Medicine, Feinberg School of Medicine, Northwestern University, 303 E. Superior Street, Chicago, IL, USA
E-mail: yanis.boumber@northwestern.edu

^d Cedars-Sinai Medical Center, Department of Medicine, Los Angeles, CA, USA

^e Fox Chase Cancer Center, Philadelphia, PA, USA

^f North Caucasus Federal University, Stavropol, Russia

^g Thai Nguyen University of Education, 20 Luong Ngoc Quyen, Thai Nguyen 24000, Vietnam

^h Institute for Tropical Technology, Vietnam Academy of Science and Technology, Hanoi, Vietnam

ⁱ Thai Nguyen University of Sciences, Tan Thinh Ward, Thai Nguyen 24000, Vietnam

^j Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Chekhov Ave., 41, Rostov-on-Don, Russia
E-mail: sayapin@ipoc.sfedu.ru

Abstract

Tropolones are promising organic compounds that can have important biologic effects. We developed a series of new 2-quinolyl-1,3-tropolones derivatives that were prepared by the acid-catalyzed reaction of 4,7-dichloro-2-methylquinolines with 1,2-benzoquinones. 2-Quinolyl-1,3-tropolones have been synthesized and tested for their anti-proliferative activity against several human cancer cell lines. Two compounds (3d and mixture B of 3i–k) showed excellent activity against six cancer cell lines of different tissue of origin. The promising compounds 3d and mixture B of 3i–k also demonstrated induction of apoptotic cell death of ovarian cancer (OVCAR-3, OVCAR-8) and colon cancer (HCT 116) cell lines and affected ERK signaling. In summary, 2-quinolyl-1,3-tropolones are promising compounds for development of effective anticancer agents.

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Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents†

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Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents

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