Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Tara Man Kadayat; Chanmi Park; Kyu Yeon Jun; Til Bahadur Thapa Magar; Ganesh Bist; Han Young Yoo; Youngjoo Kwon; Eung Seok Lee

doi:10.1016/j.bmc.2014.11.010

Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Tara Man Kadayat, Chanmi Park, Kyu Yeon Jun, Til Bahadur Thapa Magar, Ganesh Bist, Han Young Yoo, Youngjoo Kwon, Eung Seok Lee

Pharmaceutical Sciences

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

27 Scopus citations

Abstract

For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines. Among prepared 30 compounds, 7, 8, 9, 10, 12, 14, 16, 19, 20, 22, and 23 with 2- or 3-furyl and/or 2- or 3-thienyl either at 2- or 4-position of central pyridine showed the significant or moderate topoisomerase II inhibitory activity. Compounds 7, 8, 11, 12, 13, and 22 with 2-furyl, 2-thienyl or 3-thienyl at 2-position of central pyridine showed the significant or moderate topoisomerase I inhibitory activity. Especially, compound 12 with strong topoisomerase II inhibitory activity at 100 μM and 20 μM, and moderate topoisomerase I inhibitory activity displayed strong cytotoxicity against several human cancer cell lines.

Original language	English
Pages (from-to)	160-173
Number of pages	14
Journal	Bioorganic and Medicinal Chemistry
Volume	23
Issue number	1
DOIs	https://doi.org/10.1016/j.bmc.2014.11.010
State	Published - 1 Jan 2015

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01046188 ).

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

Keywords

2,4-Diaryl-5H-indeno[1,2-b]pyridine
Anticancer agents
Cytotoxicity
I and
II inhibition
Topoisomerase

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title = "Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity",

abstract = "For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines. Among prepared 30 compounds, 7, 8, 9, 10, 12, 14, 16, 19, 20, 22, and 23 with 2- or 3-furyl and/or 2- or 3-thienyl either at 2- or 4-position of central pyridine showed the significant or moderate topoisomerase II inhibitory activity. Compounds 7, 8, 11, 12, 13, and 22 with 2-furyl, 2-thienyl or 3-thienyl at 2-position of central pyridine showed the significant or moderate topoisomerase I inhibitory activity. Especially, compound 12 with strong topoisomerase II inhibitory activity at 100 μM and 20 μM, and moderate topoisomerase I inhibitory activity displayed strong cytotoxicity against several human cancer cell lines.",

keywords = "2,4-Diaryl-5H-indeno[1,2-b]pyridine, Anticancer agents, Cytotoxicity, I and, II inhibition, Topoisomerase",

author = "Kadayat, {Tara Man} and Chanmi Park and Jun, {Kyu Yeon} and Magar, {Til Bahadur Thapa} and Ganesh Bist and Yoo, {Han Young} and Youngjoo Kwon and Lee, {Eung Seok}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01046188 ). Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.bmc.2014.11.010",

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AU - Kadayat, Tara Man

AU - Park, Chanmi

AU - Jun, Kyu Yeon

AU - Magar, Til Bahadur Thapa

AU - Bist, Ganesh

AU - Yoo, Han Young

AU - Kwon, Youngjoo

AU - Lee, Eung Seok

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( NRF-2012R1A2A2A01046188 ). Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

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Y1 - 2015/1/1

N2 - For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines. Among prepared 30 compounds, 7, 8, 9, 10, 12, 14, 16, 19, 20, 22, and 23 with 2- or 3-furyl and/or 2- or 3-thienyl either at 2- or 4-position of central pyridine showed the significant or moderate topoisomerase II inhibitory activity. Compounds 7, 8, 11, 12, 13, and 22 with 2-furyl, 2-thienyl or 3-thienyl at 2-position of central pyridine showed the significant or moderate topoisomerase I inhibitory activity. Especially, compound 12 with strong topoisomerase II inhibitory activity at 100 μM and 20 μM, and moderate topoisomerase I inhibitory activity displayed strong cytotoxicity against several human cancer cell lines.

AB - For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines. Among prepared 30 compounds, 7, 8, 9, 10, 12, 14, 16, 19, 20, 22, and 23 with 2- or 3-furyl and/or 2- or 3-thienyl either at 2- or 4-position of central pyridine showed the significant or moderate topoisomerase II inhibitory activity. Compounds 7, 8, 11, 12, 13, and 22 with 2-furyl, 2-thienyl or 3-thienyl at 2-position of central pyridine showed the significant or moderate topoisomerase I inhibitory activity. Especially, compound 12 with strong topoisomerase II inhibitory activity at 100 μM and 20 μM, and moderate topoisomerase I inhibitory activity displayed strong cytotoxicity against several human cancer cell lines.

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Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Abstract

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Keywords

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