Synthesis, molecular modeling and NAD(P)H:quinone oxidoreductase 1 inducer activity of novel cyanoenone and enone benzenesulfonamides

References

• Genç Y, Özkanca R, Bekdemir Y. Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococus aureus. Ann Clin Microbiol Antimicrob 2008;7:Art No. 17 . doi:10.1186/1476-0711-7-17
   Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
   PubMed Web of Science ®Google Scholar
• Sondhi SM, Rani R, Gupta PP, et al. Synthesis, anticancer, and anti-inflammatory activity evaluation of methanesulfonamide and amidine derivatives of 3,4-diaryl-2-imino-4-thiazolines. Mol Div 2009;13:357–66
   PubMed Web of Science ®Google Scholar
• Casini A, Scozzafava A, Mastrolorenzo A, Supuran LT. Sulfonamides and sulfonylated derivatives as anticancer agents. Curr Cancer Drug Targets 2002;2:55–75
   PubMed Web of Science ®Google Scholar
• Supuran CT, Vullo D, Manole G, et al. Designing of novel carbonic anhydrase inhibitors and activators. Curr Med Chem Cardiovasc Hematol Agents 2004;2:49–68
   PubMedGoogle Scholar
• Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamides. Curr Med Chem 2003;10:925–53
   PubMed Web of Science ®Google Scholar
• Magda A, Massoud MA, Tantawy AS, et al. Synthesis and biological evaluation of new unsaturated derivatives of cyclic compounds as potent antioxidant agent. Der Pharma Chemica 2012;5:1785--97
   Google Scholar
• Kalra S, Knatko EV, Zhang Y, et al. Highly potent activation of Nrf2 by topical tricyclic bis(cyano enone): implications for protection against UV radiation during thiopurine therapy. Cancer Prev Res 2012;5:973–81
   PubMed Web of Science ®Google Scholar
• Ross D. Quinone reductases multitasking in the metabolic world. Drug Metab Rev 2004;36:639–54
   PubMed Web of Science ®Google Scholar
• Dinkova-Kostova AT, Talalay P. Nad(P)H:quinone acceptor oxidoreductase 1 (Nqo1), a multifunctional antioxidant enzyme and exceptionally versatile cytoprotector. Arch Biochem Biophys 2010;501:116–23
   PubMed Web of Science ®Google Scholar
• Itoh K, Chiba T, Takahashi S, et al. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem Biophys Res Commun 1997;236:313–22
   PubMed Web of Science ®Google Scholar
• Kensler TW, Wakabayashi N, Biswal S. Cell survival responses to environmental stresses via the Keap1-Nrf2-Are pathway. Annu Rev Pharmacol Toxicol 2007;47:89–116
   PubMed Web of Science ®Google Scholar
• Taguchi K, Motohashi H, Yamamoto M. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 2011;16:123–40
   PubMed Web of Science ®Google Scholar
• Kobayashi M, Li L, Iwamoto N, et al. 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
   PubMed Web of Science ®Google Scholar
• McMahon M, Lamont DJ, Beattie KA, Hayes JD. 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
   PubMed Web of Science ®Google Scholar
• Dinkova-Kostova AT, Talalay P, Sharkey J, et al. An exceptionally potent inducer of cytoprotective enzymes: elucidation of the structural features that determine inducer potency and reactivity with Keap1. J Biol Chem 2010;285:33747–55
   PubMed Web of Science ®Google Scholar
• Honda T, Yoshizawa H, Sundararajan C, et al. Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. J Med Chem 2011;54:1762–78
   PubMed Web of Science ®Google Scholar
• Zheng S, Santosh Laxmi YR, David E, et al. Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents. J Med Chem 2012;55:4837–46
   PubMed Web of Science ®Google Scholar
• Dinkova-Kostova AT, Kostov RV. Glucosinolates and isothiocyanates in health and disease. Trends Mol Med 2012;18:337–47
   PubMed Web of Science ®Google Scholar
• Al-Said MS, Bashandy MS, Al-Qasoumi SI, Ghorab MM. Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives. Eur J Med Chem 2011;46:137–41
   PubMed Web of Science ®Google Scholar
• Al-Said MS, Ghorab MM, Al-Dosari MS,Hamed MM. Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzenesulfonamide moiety. Eur J Med Chem 2011;46:201–7
   PubMed Web of Science ®Google Scholar
• Alqasoumi SI, Al-Taweel AM, Alafeefy AM, et al. Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents. Eur J Med Chem 2010;45:1849–53
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Ragab FA, Heiba HI, et al. In vitro anticancer screening and radiosensitizing evaluation of some new quinolines and pyrimido[4,5-b]quinolines bearing a sulfonamide moiety. Eur J Med Chem 2010;45:3677–84
   PubMed Web of Science ®Google Scholar
• Alafeefy AM, Isik S, Abdel-Aziz HA, et al. Carbonic anhydrase inhibitors: benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII. Bioorg Med Chem 2013;21:1396–403
   PubMed Web of Science ®Google Scholar
• Marcotte D, Zeng W, Hus JC, et al. Small molecules inhibit the interaction of Nrf2 and the Keap1 Kelch domain through a non-covalent mechanism. Bioorg Med Chem 2013;21:4011–19
   PubMed Web of Science ®Google Scholar
• Magesh S, Chen Y, Hu L. Small molecule modulators of Keap1-Nrf2-Are pathway as potential preventive and therapeutic agents. Med Res Rev 2012;32:687–726
   PubMed Web of Science ®Google Scholar
• Couch RD, Browning RG, Honda T, et al. Studies on the reactivity of Cddo, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action. Bioorg Med Chem Lett 2005;15:2215–19
   PubMed Web of Science ®Google Scholar
• Serafimova IM, Pufall MA, Krishnan S, et al. Reversible targeting of noncatalytic cysteines with chemically tuned electrophiles. Nat Chem Biol 2012;8:471–6
   PubMed Web of Science ®Google Scholar