Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation

Archives of Pharmacal Research

Volumn 31, Issue 2, 2008, Pages 133-141

  Kwak, Jae Hwan ^a   Won, Sun Woo ^a   Kim, Tae Jeong ^a   Roh, Eunmiri ^a   Kang, Han Young ^a   Lee, Hyo Won ^a   Jung, Jae Kyung ^a   Hwang, Bang Yeon ^a   Kim, Youngsoo ^a   Cho, Jungsook ^b   Lee, Heesoon ^a  

^a Chungbuk National University   (South Korea)

^b Dongguk University College of Medicine   (South Korea)

Author keywords

Chroman 2 carboxamide; NF B inhibitor

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; CHROMAN DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; PICRIC ACID; SCAVENGER;

ANIMAL; ARTICLE; BIOSYNTHESIS; BRAIN LEVEL; CELL LINE; DRUG ANTAGONISM; DRUG EFFECT; GENETIC TRANSCRIPTION; GENETICS; LIPID PEROXIDATION; MACROPHAGE; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ANTIOXIDANTS; BRAIN CHEMISTRY; CELL LINE; CHROMANS; FREE RADICAL SCAVENGERS; INDICATORS AND REAGENTS; LIPID PEROXIDATION; LIPOPOLYSACCHARIDES; MACROPHAGES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; NF-KAPPA B; PICRATES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION, GENETIC;

EID: 42949117039     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-001-1131-4     Document Type: Article

References (14)

1. Baeuerle, P. A. and Baltimore, D., NF-κB: Ten Years After. Cell, 87, 13-20 (1996).
2. Dutta, J., Fan, Y., Gupta, N., Fan, G., and Gelinas, C., Current insights into the regulation of programmed cell death by NF-κB. Oncogene, 25, 6800-6816 (2006).
3. Gilmore, T. D., Introduction to NF-κB: players, pathways, perspectives. Oncogene, 25, 6680-6684 (2006).
4. Israel, A., Le Bail, O., Hatat, D., Piette, J., Kieran, M., Logeat, F., Wallach, D., Fellous, M., and Kourilsky, P., TNF stimulates expression of mouse MHC class I genes by inducing an NF κB-like enhancer binding activity which displaces constitutive factors. EMBO J., 8, 3793-3800 (1989).
5. Kim, B. H., Reddy, A. M., Lee, K. H., Chung, E. Y., Cho, S. M., Lee, H., Min, K. R., and Kim, Y., Inhibitory mechanism of chroman compound on LPS-induced nitric oxide production and nuclear factor-kB activation. Biochem. Biophys. Res. Commun., 325, 223-228 (2004).
6. Kwak, J.-H., Kim, B. H., Jung, J.-K., Kim, Y., Cho, J., and Lee, H., Structure-Activity Relationships of 6-Hydroxy-7-methoxychroman-2-carboxylic acid N-(substituted)phenylamides as Inhibitors of Nuclear Factor-κB Activation. Arch. Pharm. Res., 30, 1210-1215 (2007).
7. Lee, H., Lee, K., Jung, J.-K., Cho, J., and Theodorakis, E. A., Synthesis and evaluation of 6-hydroxy-7-methoxy-4-chromanone-and chroman-2-carboxamides as antioxidants. Bioorg. Med. Chem. Lett., 15, 2745-2748 (2005).
8. Ma, Q., Kinneer, K., Ye, J., and Chen, B. J., Inhibition of nuclear factor κB by phenolic antioxidants: interplay between antioxidant signaling and inflammatory cytokine expression. Mol. Pharmacol., 64, 211-219 (2003).
9. May, M. J. and Ghosh, S., Signal transduction through NF-κB. Immunol. Today, 19, 80-88 (1998).
10. McKay, L. I. and Cidlowski, J. A., Molecular control of immune/inflammatory responses: interactions between nuclear factorkB and steroid receptor-signaling pathways. Endocr Rev., 20, 435-459 (1999).
11. Michiels, C., Minet, E., Mottet, D., and Raes, M., Regulation of gene expression by oxygen: NF-κB and HIF-1, two extremes. Free Radical Biology and Medicine, 33, 1231-1242 (2002).
12. Osborn, L., Kunkel, S., and Nabel, G. J., Tumor necrosis factor a and interleukin 1 stimulate the human immunodeficiency virus enhancer by activation of the nuclear factor κB. Proc. Natl. Acad. Sci. U.S.A., 86, 2336-2340 (1989).
13. Pande, V. and Ramos, M. J., Nuclear factor kappa B: a potential target for anti-HIV chemotherapy. Curr. Med. Chem., 10, 1603-1615 (2003).
14. Sen, R. and Baltimore, D., Inducibility of k immunoglobulin enhancer-binding protein NF-κB by a posttranslational mechanism. Cell, 47, 921-928 (1986).