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, 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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4555-4571
Number of pages	17
Journal	RSC Advances
Volume	11
Issue number	8
DOIs	https://doi.org/10.1039/d0ra10610k
State	Published - Jan 22 2021

Funding

This work was nancially supported by Vietnam National Foundation for Science and Technology Development “NAFOSTED” [grant 104.01-2015.68]; E. G. thanks the scholarship of the President RF [grant number SP-3728.2019.4]. Y. B. and I. T. were supported in part by the NIH R21 CA223394, NIH R01 CA218802 grants and by the NCI NIH Core Grant P30 CA060553 to the Robert H Lurie Comprehensive Cancer Center at Northwestern University. I. S. was supported by the NCI NIH Core Grant P30 CA006927 to Fox Chase Cancer Center. Yu. S. worked within the framework of the State Assignment of Southern Scientic Centre of RAS [grant number 01201354239]. E. B. was supported by RSF [grant number 19-74-10022]. Finally, this study was supported by the program for Competitive Growth of the Kazan Federal University (E. B., I. T., A. M., I. S., Z. A., and Y. B.).

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1039/d0ra10610k

Cite this

Gusakov, E. A., Topchu, I. A., Mazitova, A. M., Dorogan, I. V., Bulatov, E. R., Serebriiskii, I. G., Abramova, Z. I., Tupaeva, I. O., Demidov, O. P., Toan, D. N., Lam, T. D., Bang, D. N., Boumber, Y. A., Sayapin, Y. A., & Minkin, V. I. (2021). Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents. RSC Advances, 11(8), 4555-4571. https://doi.org/10.1039/d0ra10610k

@article{513f8bd59ac3496f881f6f5f380af689,

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

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.",

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

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2021",

month = jan,

day = "22",

doi = "10.1039/d0ra10610k",

language = "English (US)",

volume = "11",

pages = "4555--4571",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "8",

}

Gusakov, EA, Topchu, IA, Mazitova, AM, Dorogan, IV, Bulatov, ER, Serebriiskii, IG, Abramova, ZI, Tupaeva, IO, Demidov, OP, Toan, DN, Lam, TD, Bang, DN, Boumber, YA, Sayapin, YA & Minkin, VI 2021, 'Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents', RSC Advances, vol. 11, no. 8, pp. 4555-4571. https://doi.org/10.1039/d0ra10610k

TY - JOUR

T1 - Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents

AU - Gusakov, Evgeniy A.

AU - Topchu, Iuliia A.

AU - Mazitova, Aleksandra M.

AU - Dorogan, Igor V.

AU - Bulatov, Emil R.

AU - Serebriiskii, Ilya G.

AU - Abramova, Zinaida I.

AU - Tupaeva, Inna O.

AU - Demidov, Oleg P.

AU - Toan, Duong Ngoc

AU - Lam, Tran Dai

AU - Bang, Duong Nghia

AU - Boumber, Yanis A.

AU - Sayapin, Yurii A.

AU - Minkin, Vladimir I.

PY - 2021/1/22

Y1 - 2021/1/22

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85100133501&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85100133501&partnerID=8YFLogxK

U2 - 10.1039/d0ra10610k

DO - 10.1039/d0ra10610k

M3 - Article

C2 - 33996031

AN - SCOPUS:85100133501

SN - 2046-2069

VL - 11

SP - 4555

EP - 4571

JO - RSC Advances

JF - RSC Advances

IS - 8

ER -

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

Abstract

Funding

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

CCDC 2040512: Experimental Crystal Structure Determination

Cite this

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

Abstract

Funding

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2040512: Experimental Crystal Structure Determination

Cite this