2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study

Pritam Thapa; Radha Karki; Uttam Thapa; Yurngdong Jahng; Mi Ja Jung; Jung Min Nam; Younghwa Na; Youngjoo Kwon; Eung Seok Lee

doi:10.1016/j.bmc.2009.10.049

2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study

Pritam Thapa, Radha Karki, Uttam Thapa, Yurngdong Jahng, Mi Ja Jung, Jung Min Nam, Younghwa Na, Youngjoo Kwon, Eung Seok Lee

Department of Pharmaceutical Sciences

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

64 Scopus citations

Abstract

Designed and synthesized 60 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activities at 20 μM and 100 μM and cytotoxicity against several human cancer cell lines. Compounds 8, 9, 11-29 showed significant topoisomerase II inhibitory activity and compounds 10 and 11 showed significant topoisomerase I inhibitory activity. Most of the compounds (7-21) possessing 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety showed higher or similar cytotoxicity against HCT15 cell line as compared to standards. Most of the selected compounds displayed moderate cytotoxicity against MCF-7, HeLa, DU145, and K562 cell lines. Structure-activity relationship study revealed that 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety has an important role in displaying biological activities.

Original language	English
Pages (from-to)	377-386
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	1
DOIs	https://doi.org/10.1016/j.bmc.2009.10.049
State	Published - 1 Jan 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-(5-Chlorothiophen-2-yl)-4-(furan-3-yl)
2-Thienyl-4-furyl-6-aryl pyridine
Cytotoxicity
Topoisomerase I and II

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title = "2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study",

abstract = "Designed and synthesized 60 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activities at 20 μM and 100 μM and cytotoxicity against several human cancer cell lines. Compounds 8, 9, 11-29 showed significant topoisomerase II inhibitory activity and compounds 10 and 11 showed significant topoisomerase I inhibitory activity. Most of the compounds (7-21) possessing 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety showed higher or similar cytotoxicity against HCT15 cell line as compared to standards. Most of the selected compounds displayed moderate cytotoxicity against MCF-7, HeLa, DU145, and K562 cell lines. Structure-activity relationship study revealed that 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety has an important role in displaying biological activities.",

keywords = "2-(5-Chlorothiophen-2-yl)-4-(furan-3-yl), 2-Thienyl-4-furyl-6-aryl pyridine, Cytotoxicity, Topoisomerase I and II",

author = "Pritam Thapa and Radha Karki and Uttam Thapa and Yurngdong Jahng and Jung, {Mi Ja} and Nam, {Jung Min} and Younghwa Na 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 ).",

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doi = "10.1016/j.bmc.2009.10.049",

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AU - Karki, Radha

AU - Thapa, Uttam

AU - Jahng, Yurngdong

AU - Jung, Mi Ja

AU - Nam, Jung Min

AU - Na, Younghwa

AU - Kwon, Youngjoo

AU - Lee, Eung Seok

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N2 - Designed and synthesized 60 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activities at 20 μM and 100 μM and cytotoxicity against several human cancer cell lines. Compounds 8, 9, 11-29 showed significant topoisomerase II inhibitory activity and compounds 10 and 11 showed significant topoisomerase I inhibitory activity. Most of the compounds (7-21) possessing 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety showed higher or similar cytotoxicity against HCT15 cell line as compared to standards. Most of the selected compounds displayed moderate cytotoxicity against MCF-7, HeLa, DU145, and K562 cell lines. Structure-activity relationship study revealed that 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety has an important role in displaying biological activities.

AB - Designed and synthesized 60 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activities at 20 μM and 100 μM and cytotoxicity against several human cancer cell lines. Compounds 8, 9, 11-29 showed significant topoisomerase II inhibitory activity and compounds 10 and 11 showed significant topoisomerase I inhibitory activity. Most of the compounds (7-21) possessing 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety showed higher or similar cytotoxicity against HCT15 cell line as compared to standards. Most of the selected compounds displayed moderate cytotoxicity against MCF-7, HeLa, DU145, and K562 cell lines. Structure-activity relationship study revealed that 2-(5-chlorothiophen-2-yl)-4-(furan-3-yl) moiety has an important role in displaying biological activities.

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2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study

Abstract

Bibliographical note

Keywords

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