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KMID : 0043320160390050618
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Archives of Pharmacal Research
2016 Volume.39 No. 5 p.618 ~ p.630
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Design and synthesis of 2,3-dihydro- and 5-chloro-2,3-dihydro-naphtho-[1,2-b]furan-2-carboxylic acid N-(substitutedphenyl)amide analogs and their biological activities as inhibitors of NF-κB activity and anticancer agents
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Choi Min-Ho
Jo Hye-Ju
Kim Da-Young
Yun Ji-Eun
Kang Jong-Soon
Kim Young-Soo
Jung Jae-Kyung
Hong Jin-Tae
Cho Jung-Sook
Kwak Jae-Hwan
Lee Hee-Soon
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Abstract
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A series of 2,3-dihydro- and 5-chloro-2,3-dihydro-naphtho-[1,2-b]furan-2-carboxylic acid N-(substitutedphenyl)amide analogs (1a?k and 2a?i) were designed and synthesized for developing novel naphthofuran scaffolds as anticancer agents and inhibitors of NF-κB activity. Compound 1d, which had a 4′-chloro group on the N-phenyl ring, exhibited inhibitory activity of NF-κB. Compound 2g, which had a 5′-chloro group on the naphthofuran ring and a 3′,5′-bistrifluoromethane group on the N-phenyl ring, had the best NF-κB inhibitory activity. In addition, the novel analogs exhibited potent cytotoxicity at low concentrations against HCT-116, NCI-H23, and PC-3 cell lines. The two electron-withdrawing groups, especially at the 3′,5′-position on the N-phenyl ring, increased anticancer activity and NF-κB inhibitory activity. However, only 5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-carboxylic N-(3′,5′-bis(trifluoromethyl)phenyl)amide (2g) exhibited both outstanding cytotoxicity and NF-κB inhibitory activities. This novel lead scaffold may be helpful for investigation of new anticancer agents by inactivation of NF-κB.
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KEYWORD
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Anticancer activity, Inhibition of NF-κB transcriptional activity, 2, 3-Dihydronaphtho-[1, 2-b]furan scaffolds
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