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

被引：92
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
收藏
页码：3066 / 3077
页数：12
相关论文
共 50 条
  • [31] Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells
    Lin, Chen
    Lu, Pei-Jung
    Yang, Chia-Ning
    Hulme, Christopher
    Shaw, Arthur Y.
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (05) : 2385 - 2394
  • [32] Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines
    Huang, Guang
    Solano, Claribel Murillo
    Melendez, Joel
    Shaw, Justin
    Collins, Jennifer
    Banks, Robert
    Arshadi, Arash Keshavarzi
    Boonhok, Rachasak
    Min, Hui
    Miao, Jun
    Chakrabarti, Debopam
    Yuan, Yu
    JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (20) : 11756 - 11785
  • [33] Synthesis and Antimicrobial Activity of 2-Methyl-5-nitroaniline Derivatives: A Structure-Activity Relationship Study
    Lingappa, Mallesha
    Kikkeri, N. Mahana
    Devaraju, Rakshith
    Sreedharamurthy, Satish
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (01) : 102 - 108
  • [34] Design, synthesis, biological evaluation, structure-activity relationship study, and mode of action of 2-phenol-4,6-dichlorophenyl-pyridines
    Shrestha, Aarajana
    Park, Seojeong
    Shin, Somin
    Kadayat, Tara Man
    Bist, Ganesh
    Katila, Pramila
    Kwon, Youngjoo
    Lee, Eung-Seok
    BIOORGANIC CHEMISTRY, 2018, 79 : 1 - 18
  • [35] Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase
    Christoff, Rebecca M.
    Soares da Costa, Tatiana P.
    Bayat, Saadi
    Holien, Jessica K.
    Perugini, Matthew A.
    Abbott, Belinda M.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 52
  • [36] 5-Arylidene-2(5H)-furanone derivatives: synthesis and structure-activity relationship for cytotoxicity
    Seong-Cheol Bang
    Yong Kim
    Mi-Young Yun
    Byung-Zun Ahn
    Archives of Pharmacal Research, 2004, 27 : 485 - 494
  • [37] Synthesis and SAR study of new hydroxy and chloro-substituted 2,4-diphenyl 5H-chromeno[4,3-b]pyridines as selective topoisomerase IIα-targeting anticancer agents
    Magar, Til Bahadur Thapa
    Seo, Seung Hee
    Kadayat, Tara Man
    Jo, Hyunji
    Shrestha, Aarajana
    Bist, Ganesh
    Katila, Pramila
    Kwon, Youngjoo
    Lee, Eung-Seok
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (08) : 1909 - 1919
  • [38] 5-arylidene-2(5H)-furanone derivatives:: Synthesis and structure-activity relationship for cytotoxicity
    Bang, SC
    Kim, Y
    Yun, MY
    Ahn, BZ
    ARCHIVES OF PHARMACAL RESEARCH, 2004, 27 (05) : 485 - 494
  • [39] The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure-Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles
    Al-Refai, Mahmoud
    Ibrahim, Mohammad M.
    Azmi, Mohamad Nurul
    Osman, Hasnah
    Abu Bakar, Mohamad Hafizi
    Geyer, Armin
    MOLECULES, 2019, 24 (22):
  • [40] Synthesis and structure-activity relationship of 2-arylamino-4-aryl-pyrimidines as potent PAK1 inhibitors
    Xu, Yong
    Foulks, Jason M.
    Clifford, Adrianne
    Brenning, Benjamin
    Lai, Shuping
    Luo, Bai
    Parnell, K. Mark
    Merx, Shannon
    McCullar, Michael V.
    Kanner, Steven B.
    Ho, Koc-Kan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (14) : 4072 - 4075
12345