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Design, synthesis and biological evaluation of 1,3-diphenylbenzo[f] [1,7]naphthyrdines

Title
Design, synthesis and biological evaluation of 1,3-diphenylbenzo[f] [1,7]naphthyrdines
Authors
Arepalli, Sateesh KumarPark, ByeongwooLee, KihoJo, HyunjiJun, Kyu-YeonKwon, YoungjooKang, Jong-SoonJung, Jae-KyungLee, Heesoon
Ewha Authors
권영주전규연
SCOPUS Author ID
권영주scopus
Issue Date
2017
Journal Title
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN
0968-0896JCR Link1464-3391JCR Link
Citation
vol. 25, no. 20, pp. 5586 - 5597
Keywords
1,3-Diphenylbenzo[f][1,7] benzonaphthyrdinesHuman Topoisomerase II alpha inhibitorsCytotoxic agentsMolecular docking studiesImino Diels-Alder reaction
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
A novel series of twenty 1,3-diphenylbenzo[f][1,7]benzonaphthyrdine derivatives were designed and synthesized through intermolecular imino Diels-Alder reaction. Their in vitro cytotoxic activities were evaluated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Majority of synthesized compounds exhibited significant cytotoxic activities against all tested human cancer cell lines. Among them 4l, 4m, and 4o derivatives exhibited most promising cytotoxic activities. Furthermore these compounds were evaluated against human Topoisomerase II alpha inhibition. Interestingly, the compound 4l exhibited 1.3 and 1.2 times more potent human Topoisomerase II alpha inhibition than the reference drug etoposide in both 100 mu M and 20 mu M concentrations respectively. Molecular docking studies for the compound 4l have also been executed by Sybyl X-2.1 in which it reveals the binding site of the compound 4l with topo II alpha DNA cleavage site where etoposide was situated. The benzo[f][1,7]naphthyridine ring was stacked between the DNA bases of the cleavage site. (C) 2017 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.bmc.2017.08.030
Appears in Collections:
약학대학 > 약학과 > Journal papers
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