Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship

Pritam Thapa; Radha Karki; Hoyoung Choi; Jae Hun Choi; Minho Yun; Byeong Seon Jeong; Mi Ja Jung; Jung Min Nam; Younghwa Na; Won Jea Cho; Youngjoo Kwon; Eung Seok Lee

doi:10.1016/j.bmc.2010.01.065

Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship

Pritam Thapa, Radha Karki, Hoyoung Choi, Jae Hun Choi, Minho Yun, Byeong Seon Jeong, Mi Ja Jung, Jung Min Nam, Younghwa Na, Won Jea Cho, Youngjoo Kwon, Eung Seok Lee

Department of Pharmaceutical Sciences

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

44 Scopus citations

Abstract

A series of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives were designed, synthesized, and evaluated for their topoisomerase I and II inhibition and cytotoxic activity against several human cancer cell lines. Compounds 10-19 showed moderate topoisomerase I and II inhibitory activity and 20-29 showed significant topoisomerase II inhibitory activity. Structure-activity relationship study revealed that 4-(5-chlorofuran-2-yl)-2-(thiophen-3-yl) moiety has an important role in displaying topoisomerase II inhibition.

Original language	English
Pages (from-to)	2245-2254
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmc.2010.01.065
State	Published - 15 Mar 2010

Bibliographical note

Funding Information:
This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( R11-2007-040-02004-0 ).

Keywords

2-(Thienyl-2-yl)-4-furyl-6-aryl pyridine
2-(Thienyl-3-yl)-4-furyl-6-aryl pyridine
Cytotoxicity
Topoisomerase I and II inhibition

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Thapa, P., Karki, R., Choi, H., Choi, J. H., Yun, M., Jeong, B. S., Jung, M. J., Nam, J. M., Na, Y., Cho, W. J., Kwon, Y., & Lee, E. S. (2010). Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship. Bioorganic and Medicinal Chemistry, 18(6), 2245-2254. https://doi.org/10.1016/j.bmc.2010.01.065

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title = "Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship",

abstract = "A series of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives were designed, synthesized, and evaluated for their topoisomerase I and II inhibition and cytotoxic activity against several human cancer cell lines. Compounds 10-19 showed moderate topoisomerase I and II inhibitory activity and 20-29 showed significant topoisomerase II inhibitory activity. Structure-activity relationship study revealed that 4-(5-chlorofuran-2-yl)-2-(thiophen-3-yl) moiety has an important role in displaying topoisomerase II inhibition.",

keywords = "2-(Thienyl-2-yl)-4-furyl-6-aryl pyridine, 2-(Thienyl-3-yl)-4-furyl-6-aryl pyridine, Cytotoxicity, Topoisomerase I and II inhibition",

author = "Pritam Thapa and Radha Karki and Hoyoung Choi and Choi, {Jae Hun} and Minho Yun and Jeong, {Byeong Seon} and Jung, {Mi Ja} and Nam, {Jung Min} and Younghwa Na and Cho, {Won Jea} and Youngjoo Kwon and Lee, {Eung Seok}",

note = "Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( R11-2007-040-02004-0 ).",

year = "2010",

month = mar,

day = "15",

doi = "10.1016/j.bmc.2010.01.065",

language = "English",

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Thapa, P, Karki, R, Choi, H, Choi, JH, Yun, M, Jeong, BS, Jung, MJ, Nam, JM, Na, Y, Cho, WJ, Kwon, Y & Lee, ES 2010, 'Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship', Bioorganic and Medicinal Chemistry, vol. 18, no. 6, pp. 2245-2254. https://doi.org/10.1016/j.bmc.2010.01.065

Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship. / Thapa, Pritam; Karki, Radha; Choi, Hoyoung et al.
In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 6, 15.03.2010, p. 2245-2254.

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

TY - JOUR

T1 - Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship

AU - Thapa, Pritam

AU - Karki, Radha

AU - Choi, Hoyoung

AU - Choi, Jae Hun

AU - Yun, Minho

AU - Jeong, Byeong Seon

AU - Jung, Mi Ja

AU - Nam, Jung Min

AU - Na, Younghwa

AU - Cho, Won Jea

AU - Kwon, Youngjoo

AU - Lee, Eung Seok

N1 - Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( R11-2007-040-02004-0 ).

PY - 2010/3/15

Y1 - 2010/3/15

N2 - A series of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives were designed, synthesized, and evaluated for their topoisomerase I and II inhibition and cytotoxic activity against several human cancer cell lines. Compounds 10-19 showed moderate topoisomerase I and II inhibitory activity and 20-29 showed significant topoisomerase II inhibitory activity. Structure-activity relationship study revealed that 4-(5-chlorofuran-2-yl)-2-(thiophen-3-yl) moiety has an important role in displaying topoisomerase II inhibition.

AB - A series of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives were designed, synthesized, and evaluated for their topoisomerase I and II inhibition and cytotoxic activity against several human cancer cell lines. Compounds 10-19 showed moderate topoisomerase I and II inhibitory activity and 20-29 showed significant topoisomerase II inhibitory activity. Structure-activity relationship study revealed that 4-(5-chlorofuran-2-yl)-2-(thiophen-3-yl) moiety has an important role in displaying topoisomerase II inhibition.

KW - 2-(Thienyl-2-yl)-4-furyl-6-aryl pyridine

KW - 2-(Thienyl-3-yl)-4-furyl-6-aryl pyridine

KW - Cytotoxicity

KW - Topoisomerase I and II inhibition

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SN - 0968-0896

VL - 18

SP - 2245

EP - 2254

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 6

ER -

Synthesis of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship

Abstract

Bibliographical note

Keywords

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