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

Designed and synthesized 48 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines. A series of 2-(thienyl-2-yl or -3-yl)-4-furyl-6-aryl pyridine derivatives were designed, synthesized...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2010-03, Vol.18 (6), p.2245-2254
Main Authors: Thapa, Pritam, Karki, Radha, Choi, Hoyoung, Choi, Jae Hun, Yun, Minho, Jeong, Byeong-Seon, Jung, Mi-Ja, Nam, Jung Min, Na, Younghwa, Cho, Won-Jea, Kwon, Youngjoo, Lee, Eung-Seok
Format: Article
Language:English
Subjects:
2-(Thienyl-2-yl)-4-furyl-6-aryl pyridine
2-(Thienyl-3-yl)-4-furyl-6-aryl pyridine
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Proliferation - drug effects
Cytotoxicity
DNA Topoisomerases, Type I - chemistry
DNA Topoisomerases, Type I - metabolism
DNA Topoisomerases, Type II - chemistry
DNA Topoisomerases, Type II - metabolism
Drug Design
Drug Screening Assays, Antitumor
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Humans
Molecular Structure
Pyridines - chemical synthesis
Pyridines - chemistry
Pyridines - pharmacology
Stereoisomerism
Structure-Activity Relationship
Topoisomerase I and II inhibition
Topoisomerase I Inhibitors
Topoisomerase II Inhibitors
Tumor Cells, Cultured
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Summary:Designed and synthesized 48 2-thienyl-4-furyl-6-aryl pyridine derivatives were evaluated for their topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines. 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.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2010.01.065