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

45 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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10.1016/j.bmc.2010.01.065

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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",

volume = "18",

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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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M3 - Article

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AN - SCOPUS:77649237047

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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