Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of hydroxylated 2,4-diphenyl-6-aryl pyridines

被引：94

作者：

Karki, Radha ^{[3
]}

Thapa, Pritam ^{[3
]}

Kang, Mi Jeong ^{[3
]}

Jeong, Tae Cheon ^{[3
]}

Nam, Jung Min ^{[1
,2
]}

Kim, Hye-Lin ^{[1
,2
]}

Na, Younghwa ^{[4
]}

Cho, Won-Jea ^{[5
]}

Kwon, Youngjoo ^{[1
,2
]}

Lee, Eung-Seok ^{[3
]}

机构：

[1] Ewha Womans Univ, Coll Pharm, Seoul 120750, South Korea

[2] Ewha Womans Univ, Div Life & Pharmaceut Sci, Seoul 120750, South Korea

[3] Yeungnam Univ, Coll Pharm, Kyongsan 712749, South Korea

[4] Catholic Univ Daegu, Coll Pharm, Kyongsan 712702, South Korea

[5] Chonnam Natl Univ, Coll Pharm, Kwangju 500757, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 09期

关键词：

Hydroxylated 2,4-diphenyl-6-aryl pyridines; Topoisomerase I and II inhibitor; Cytotoxicity; Anticancer agents; DNA TOPOISOMERASES; CANCER CELLS; DERIVATIVES; COMPLEXES; COVALENT; AGENTS;

D O I：

10.1016/j.bmc.2010.03.051

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new series of 2,4-diphenyl-6-aryl pyridines containing hydroxyl group(s) at the ortho, meta, or para position of the phenyl ring were synthesized, and evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Structure-activity relationship study revealed that the substitution of hydroxyl group( s) increased topoisomerase I and II inhibitory activity in the order of meta > para > ortho position. Substitution of hydroxyl group on the para position showed better cytotoxicity. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3066 / 3077

页数：12

共 31 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] 2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure-activity relationship, and docking study [J].

Basnet, Arjun ;

Thapa, Pritam ;

Karki, Radha ;

Choi, Hoyoung ;

Choi, Jae Hun ;

Yun, Minho ;

Jeong, Byeong-Seon ;

Jahng, Yurngdong ;

Na, Younghwa ;

Cho, Won-Jea ;

Kwon, Youngjoo ;

Lee, Chong-Soon ;

Lee, Eung-Seok .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) :42-47

[3] Synthetic chalcones, flavanones, and flavones as antitumoral agents:: Biological evaluation and structure-activity relationships [J].

Cabrera, Mauricio ;

Simoens, Macarena ;

Falchi, Gabriela ;

Lavaggi, M. Laura ;

Piro, Oscar E. ;

Castellano, Eduardo E. ;

Vidal, Anabel ;

Azqueta, Amaia ;

Monge, Antonio ;

de Cerain, Adela Lopez ;

Sagrera, Gabriel ;

Scoane, Gustavo ;

Cerecetto, Hugo ;

Gonzalez, Mercedes .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3356-3367

[4] 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

[5] DNA topoisomerases: Structure, function, and mechanism [J].

Champoux, JJ .

ANNUAL REVIEW OF BIOCHEMISTRY, 2001, 70 :369-413

[6] Resveratrol as a chemopreventive agent:: A promising molecule for fighting cancer [J].

Delmas, D ;

Lançon, A ;

Colin, D ;

Jannin, B ;

Latruffe, N .

CURRENT DRUG TARGETS, 2006, 7 (04) :423-442

[7] Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin [J].

Fan, Y ;

Weinstein, JN ;

Kohn, KW ;

Shi, LM ;

Pommier, Y .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (13) :2216-2226

[8]

Fukuda M, 1996, CANCER RES, V56, P789

[9]

GIJN RV, 2000, J ONCOL PHARM PRACTI, V3, P92

[10] Simple aromatic compounds containing propenone moiety show considerable dual COX/5-LOX inhibitory activities [J].

Jahng, Y ;

Zhao, LX ;

Moon, YS ;

Basnet, A ;

Kim, EK ;

Chang, HW ;

Ju, HK ;

Jeong, TC ;

Lee, ES .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (10) :2559-2562

← 1 2 3 4 →