2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure-activity relationship, and docking study

被引:46
作者
Basnet, Arjun [1 ]
Thapa, Pritam [1 ]
Karki, Radha [1 ]
Choi, Hoyoung [1 ]
Choi, Jae Hun [1 ]
Yun, Minho [1 ]
Jeong, Byeong-Seon [1 ]
Jahng, Yurngdong [1 ]
Na, Younghwa [2 ]
Cho, Won-Jea [3 ]
Kwon, Youngjoo [4 ]
Lee, Chong-Soon [5 ]
Lee, Eung-Seok [1 ]
机构
[1] Yeungnam Univ, Coll Pharm, Kyongsan 712749, South Korea
[2] Catholic Univ Daegu, Coll Pharm, Kyongsan 712702, South Korea
[3] Chonnam Natl Univ, Coll Pharm, Kwangju 500757, South Korea
[4] Ewha Womans Univ, Coll Pharm, Pharm & Div Life & Pharmaceut Sci, Seoul 120750, South Korea
[5] Yeungnam Univ, Dept Biochem, Kyongsan 712749, South Korea
关键词
2,6-Dithienyl-4-furyl pyridine; Topoisomerase I and II inhibitor; Cytotoxicity; Antitumor agents; Docking study; SUBSTITUIERTER PYRIDINE; DNA-TOPOISOMERASES; EUROPIUM(III); COMPLEXES;
D O I
10.1016/j.bmcl.2009.11.041
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
For the development of novel antitumor agents, 2,6-dithienyl-4-furyl pyridine derivatives were prepared and evaluated for their topoisomerase I and II inhibitory activity as well as cytotoxicity against several human cancer cell lines. Among the 21 prepared compounds, compound 24 exhibited strong topoisomerase I inhibitory activity. In addition, a docking study with topoisomerase I and compound 24 was performed. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:42 / 47
页数:6
相关论文
共 33 条
[1]   2,4,6-Trisubstituted pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship [J].
Basnet, Arjun ;
Thapa, Pritam ;
Karki, Radha ;
Na, Younghwa ;
Jahng, Yurngdong ;
Jeong, Byeong-Seon ;
Jeong, Tae Cheon ;
Lee, Chong-Soon ;
Lee, Eung-Seok .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (13) :4351-4359
[2]   Structure of DNA topoisomerases [J].
Berger, JM .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1998, 1400 (1-3) :3-18
[3]   Oxidation of DNA and RNA by oxoruthenium(IV) metallointercalators: Visualizing the recognition properties of dipyridophenazine by high-resolution electrophoresis [J].
Carter, PJ ;
Cheng, CC ;
Thorp, HH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :632-642
[4]   DNA TOPOISOMERASES - ESSENTIAL ENZYMES AND LETHAL TARGETS [J].
CHEN, AY ;
LIU, LF .
ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1994, 34 :191-218
[5]  
Fukuda M, 1996, CANCER RES, V56, P789
[6]   METALLOINTERCALATION REAGENTS - 2-HYDROXYETHANETHIOLATO(2,2',2''-TERPYRIDINE)-PLATINUM(II) MONOCATION BINDS STRONGLY TO DNA BY INTERCALATION [J].
JENNETTE, KW ;
LIPPARD, SJ ;
VASSILIADES, GA ;
BAUER, WR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1974, 71 (10) :3839-3843
[7]   Cell death induced by topoisomerase-targeted drugs: more questions than answers [J].
Kaufmann, SH .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1998, 1400 (1-3) :195-211
[8]   Human DNA-topoisomerases - Diagnostic and therapeutic implications for cancer [J].
Kellner, U ;
Rudolph, P ;
Parwaresch, R .
ONKOLOGIE, 2000, 23 (05) :424-430
[9]   Novel protein kinase C inhibitors:: α-terthiophene derivatives [J].
Kim, DSHL ;
Ashendel, CL ;
Zhou, Q ;
Chang, CT ;
Lee, ES ;
Chang, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (19) :2695-2698
[10]  
Krhnke F., 1963, Angew. Chem. Int. Ed, V2, P380, DOI 10.1002/anie.196303801