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Title 

Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB

Authors 

M ChoiH JoH J ParkA S KumarJ LeeJi Eun YunY KimS B HanJ K JungJ ChoK LeeJ H KwakH Lee

Publisher 

Elsevier

Issue Date 

2015

Citation 

Bioorganic & Medicinal Chemistry Letters, vol. 25, no. 12, pp. 2545-2549

Keywords 

Anticancer activityBenzofuran and 2,3-dihydrobenzofuranInhibition of NF-κB transcriptional activityscaffolds

Abstract 

With the aim of developing novel scaffolds as anticancer agents and inhibitors of NF-κB activity, 60 novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives (1a-s, 2a-k, 3a-s, and 4a-k) were designed and synthesized from the reference lead compound KL-1156, which is an inhibitor of NF-κB translocation to the nucleus in LPS-stimulated RAW 264.7 macrophage cells. The novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxamide derivatives exhibited potent cytotoxic activities (measured by the sulforhodamine B assay) at low micromolar concentrations against six human cancer cell lines: ACHN (renal), HCT15 (colon), MM231 (breast), NUGC-3 (gastric), NCI-H23 (lung), and PC-3 (prostate). In addition, these compounds also inhibited LPS-induced NF-κB transcriptional activity. The +M effect and hydrophobic groups on the N-phenyl ring potentiated the anticancer activity and NF-κB inhibitory activity, respectively. However, according to the results of structure-activity relationship studies, only benzofuran-2-carboxylic acid N-(4′-hydroxy)phenylamide (3m) was the lead scaffold with both an outstanding anticancer activity and NF-κB inhibitory activity. This novel lead scaffold may be helpful for investigation of new anticancer agents that act through inactivation of NF-κB.

ISSN 

0960-894X

Link 

http://dx.doi.org/10.1016/j.bmcl.2015.04.050

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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