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-kB activity and anticancer agents

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Title
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-kB activity and anticancer agents
Author(s)
M Choi; H Jo; D Kim; Ji Eun Yun; Jong Soon Kang; Y Kim; J K Jung; J T Hong; J Cho; J H Kwak; H Lee
Bibliographic Citation
Archives of Pharmacal Research, vol. 39, no. 5, pp. 618-630
Publication Year
2016
Abstract
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.
Keyword
2,3-Dihydronaphtho-[1,2-b]furan scaffoldsAnticancer activityInhibition of NF-κB transcriptional activity
ISSN
0253-6269
Publisher
Pharmaceutical Soc Korea
DOI
http://dx.doi.org/10.1007/s12272-016-0737-5
Type
Article
Appears in Collections:
Ochang Branch Institute > Division of Bioinfrastructure > Laboratory Animal Resource Center > 1. Journal Articles
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