Synthesis, molecular modeling and NAD(P)H:quinone oxidoreductase 1 inducer activity of novel 2-phenylquinazolin-4-amine derivatives

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue 6, 2016, Pages 1612-1618

  Ghorab, Mostafa M ^a,b   Alsaid, Mansour S ^a   Higgins, Maureen ^c   Dinkova Kostova, Albena T ^c,d   Shahat, Abdelaaty A ^a,e   Elghazawy, Nehal H ^f   Arafa, Reem K ^f,g  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b NATIONAL CENTER FOR RADIATION RESEARCH AND TECHNOLOGY   (Egypt)

^c UNIVERSITY OF DUNDEE   (United Kingdom)

^d JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e NATIONAL RESEARCH CENTRE   (Egypt)

^f ZEWAIL CITY OF SCIENCE AND TECHNOLOGY   (Egypt)

^g CAIRO UNIVERSITY   (Egypt)

Author keywords

2 phenylquinazolin 4 amine derivatives; Cytoprotection; Keap1 Nrf2; molecular modeling; NQO1 induction

Indexed keywords

2 PHENYL 4 CHLOROQUINAZOLINE; 2 PHENYL N (5,6,7,8 TETRAHYDRONAPHTHALEN 1 YL)QUINAZOLIN 4 AMINE; 2 PHENYL N (QUINOLIN 2 YL)QUINAZOLIN 4 AMINE; 2 PHENYL N (QUINOLIN 3 YL)QUINAZOLIN 4 AMINE; 2 PHENYLQUINAZOLIN 4 AMINE DERIVATIVE; 4 METHYL 7 (2 PHENYLQUINAZOLIN 4 YLAMINO) 2H CHROMEN 2 ONE; 7 (2 PHENYLQUINAZOLIN 4 YLAMINO) 4 (TRIFLUOROMETHYL) 2H CHROMEN 2 ONE; CYTOPROTECTIVE AGENT; KELCH LIKE ECH ASSOCIATED PROTEIN 1; N (2 METHYLQUINOLIN 4 YL) 2 PHENYLQUINAZOLIN 4 AMINE; N (2,3 DIHYDRO 1H INDEN 5 YL) 2 PHENYLQUINAZOLIN 4 AMINE; N (4 MORPHOLINOPHENYL) 2 PHENYLQUINAZOLIN 4 AMINE; N (BENZO[D][1,3]DIOXOL 5 YL) 2 PHENYLQUINAZOLIN 4 AMINE; N (BENZO[D][1,3]DIOXOL 5 YLMETHYL) 2 PHENYLQUINAZOLIN 4 AMINE; N (NAPHTHALEN 1 YL) PHENYLQUINAZOLIN 4 AMINE; NAD(P)H QUINONE OXIDOREDUCTASE 1; QUINAZOLINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; 2-PHENYLQUINAZOLINE; AMINE; NQO1 PROTEIN, HUMAN;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; HEPATOMA CELL; ISOMER; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; BIOSYNTHESIS; CHEMISTRY; ENZYME INDUCTION; MASS SPECTROMETRY; MOLECULAR MODEL; MOUSE; SYNTHESIS; TUMOR CELL LINE;

AMINES; ANIMALS; CARBON-13 MAGNETIC RESONANCE SPECTROSCOPY; CELL LINE, TUMOR; ENZYME INDUCTION; MASS SPECTROMETRY; MICE; MODELS, MOLECULAR; NAD(P)H DEHYDROGENASE (QUINONE); PROTON MAGNETIC RESONANCE SPECTROSCOPY; QUINAZOLINES;

EID: 84964009499     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2016.1158714     Document Type: Article

References (25)

1. G.Waris, H.Ahsan. Reactive oxygen species:role in the development of cancer and various chronic conditions. J Carcinog 2006;5:14
2. J.G.Scandalios The rise of ROS. Trends Biochem Sci 2002;27:483–6
3. J.A.Klein, S.L.Ackerman. Oxidative stress, cell cycle, and neurodegeneration. J Clin Invest 2003;111:785–93
4. H.Ahsan, A.Ali, R.Ali Oxygen free radicals and systemic autoimmunity. Clin Exp Immunol 2003;131:398–404
5. J.A.Knight Diseases related to oxygen-derived free radicals. Ann Clin Lab Sci 1995;25:111–21
6. G.Waris, K.Alam Attenuated antigenicity of ribonucleoproteins modified by reactive oxygen species. Biochem Mol Biol Int 1998;45:33–45
7. T.W.Kensler, N.Wakabayashi, S.Biswal Cell survival responses to environmental stresses via the Keap1–Nrf2–ARE pathway. Annu Rev Pharmacol Toxicol 2007;47:89–116
8. M.Kobayashi, L.Li, N.Iwamoto,. The antioxidant defense system Keap1–Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds. Mol Cell Biol 2009;29:493–502
9. M.McMahon, D.J.Lamont, K.A.Beattie, J.D.Hayes Keap1 perceives stress via three sensors for the endogenous signaling molecules nitric oxide, zinc, and alkenals. Proc Natl Acad Sci USA 2010;107:18838–43
10. A.T.Dinkova-Kostova, W.D.Holtzclaw, R.N.Cole,. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc Natl Acad Sci USA 2002;99:11908–13
11. J.Li, T.Ichikawa, J.S.Janicki, T.Cui Targeting the Nrf2 pathway against cardiovascular disease. Expert Opin Ther Targets 2009;13:785–94
12. J.Zhao, J.B.Redell, A.N.Moore, P.K.Dash A novel strategy to activate cytoprotective genes in the injured brain. Biochem Biophys Res Commun 2011;407:501–6
13. R.Steel, J.Cowan, E.Payerne,. Anti-inflammatory effect of a cell-penetrating peptide targeting the Nrf2/Keap1 interaction. ACS Med Chem Lett 2012;3:407–10
14. T.P.Williamson, S.Amirahmadi, G.Joshi,. Discovery of potent, novel Nrf2 inducers via quantum modeling, virtual screening, and in vitro experimental validation. Chem Biol Drug Des 2012;80:810–20
15. L.Hu, S.Magesh, L.Chen,. Discovery of a small-molecule inhibitor and cellular probe of Keap1–Nrf2 protein–protein interaction. Bioorg Med Chem Lett 2013;23:3039–43
16. C.Zhuang, Z.Miao, C.Sheng, W.Zhang Updated research and applications of small molecule inhibitors of Keap1–Nrf2 protein–protein interaction:a review. Curr Med Chem 2014;21:1861–70
17. N.A.Nesterova, S.I.Kovalenko, I.F.Belenichev,. Formation of combinational library of quinazoline-4-yl-hydrazones with antioxidant activity. Ukraine Med Khim 2004;6:14–21
18. N.A.Nesterova, S.I.Kovalenko, O.V.Karpenkos, I.F.Belenichev Synthesis and antioxidant activity of 4-arylidenehydrazinoquinazolines. Ukr Farmatsevtichnii Zhurnal (Kiev) 2004;22:5–10
19. M.A.Al-Omar, S.T.Al-Rashood, H.I.El-Subbagh, S.G.Abdel Hamide Interaction of 2-thio-4-oxo-quinazoline derivatives with guinea pig liver molybdenum hydroxylases, xanthine oxidase and aldehyde oxidase. J Biol Sci 2005;5:370–8
20. M.M.Ghorab, M.Higgins, M.S.Alsaid,. Synthesis, molecular modeling and NAD(P)H:quinone oxidoreductase 1 inducer activity of novel cyanoenone and enone benzenesulfonamides. J Enzyme Inhib Med Chem 2014;29:840–5
21. M.M.Ghorab, M.Higgins, A.T.Dinkova-Kostova,. Novel thioureido derivatives carrying thione and sulfonamide moieties induce the cytoprotective enzyme NAD(P)H:quinone oxidoreductase 1. Asian J Chem 2014;26:8501–4
22. H.J.Prochaska, A.B.Santamaria Direct measurement of NAD(P)H:quinone reductase from cells cultured in microtiter wells:a screening assay for anticarcinogenic enzyme inducers. Anal Biochem 1988;169:328–36
23. D.Marcotte, W.Zeng, J.C.Hus,. Small molecules inhibit the interaction of Nrf2 and the Keap1 Kelch domain through a noncovalent mechanism. Bioorg Med Chem 2013;21:4011–19
24. S.Magesh, Y.Chen, L.Hu. Small molecule modulators of Keap1–Nrf2–ARE pathway as potential preventive and therapeutic agents. Med Res Rev 2012;32:687–726
25. H.C.Bertrand, M.Schaap, L.Baird,. Design, synthesis, and evaluation of triazole derivatives that induce Nrf2 dependent gene products and inhibit the Keap1–Nrf2 protein–protein interaction. J Med Chem 2015;58:7186–94