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Research Article

Biologically active carbazole derivatives: focus on oxazinocarbazoles and related compounds

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Pages 180-188 | Received 16 Jan 2014, Accepted 24 Feb 2014, Published online: 03 Apr 2014

References

  • Schmidt AW, Reddy KR, Knölker HJ. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev 2012;112:3193–328
  • Nagappan T, Ramasamy P, Wahid ME, et al. Biological activity of carbazole alkaloids and essential oil of Murraya koenigii against antibiotic resistant microbes and cancer cell lines. Molecules 2011;16:9651–64
  • Ma Q, Tian J, Yang J, et al. Bioactive carbazole alkaloids from Murraya koenigii (L.) Spreng. Fitoterapia 2013;87:1–6
  • Wu TS, Huang SC, Wu PL, Teng CM. Carbazole alkaloids from Clausena excavata and their biological activities. Phytochemistry 1996;43:133–40
  • Peng WW, Zeng GZ, Song WW, Tan NH. A new cytotoxic carbazole alkaloid and two new other alkaloids from Clausena excavata. Chem Biodivers 2013;10:1317–21
  • Asche C, Frank W, Albert A, Kucklaender U. Synthesis, antitumour activity and structure-activity relationships of 5H-benzo[b]carbazoles. Bioorg Med Chem 2005;13:819–37
  • Hajbi Y, Neagoie C, Biannic B, et al. Synthesis and biological activities of new furo[3,4-b]carbazoles: potential topoisomerase II inhibitors. Eur J Med Chem 2010;45:5428–37
  • Giraud F, Akué-Gédu R, Nauton L, et al. Synthesis and biological activities of 4-substituted pyrrolo[2,3-a]carbazole Pim kinase inhibitors. Eur J Med Chem 2012;56:225–36
  • Akué-Gédu R, Letribot B, Saugues E, et al. Kinase inhibitory potencies and in vitro antiproliferative activities of N-10 substituted pyrrolo[2,3-a]carbazoles derivatives. Bioorg Med Chem Lett 2012;22:3807–9
  • Lee HJ, Schaefer G, Heffron TP, et al. Noncovalent wild-type-sparing inhibitors of EGFR T790M. Cancer Discov 2013;3:168–81
  • Indumathi T, Muthusankar A, Shanmughavel P, Rajendra Prasad KJ. Synthesis of hetero annulated carbazoles: exploration of in vitro cytotoxicity and molecular docking studies. Med Chem Commun 2013;4:450–5
  • Prudent R, Moucadel V, Nguyen CH, et al. Antitumor activity of pyridocarbazole and benzopyridoindole derivatives that inhibit protein kinase CK2. Cancer Res 2010;70:9865–74
  • Liu S, Hsieh D, Yang YL, et al. Coumestrol from the national cancer Institute's natural product library is a novel inhibitor of protein kinase CK2. BMC Pharmacol Toxicol 2013;14:36
  • Robey RW, Shukla S, Steadman K, et al. Inhibition of ABCG2-mediated transport by protein kinase inhibitors with a bisindolylmaleimide or indolocarbazole structure. Mol Cancer Ther 2007;6:1877–85
  • Bandgar BP, Adsul LK, Chavan HV, et al. Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents. Bioorg Med Chem Lett 2012;22:5839–44
  • Zhang FF, Gan LL, Zhou CH. Synthesis, antibacterial and antifungal activities of some carbazoles derivatives. Bioorg Med Chem Lett 2010;20:1881–4
  • Biamonte MA, Wanner J, Le Roch KG. Recent advances in malaria drug discovery. Bioorg Med Chem Lett 2013;23:2829–43
  • Tenbrink RE. Oxazinocarbazoles for the treatment of CNS diseases, European Patent 1200447 A1; 2002
  • McCarthy TJ, Merchant KM, Ten Brink RE. Labeled oxazinocarbazoles as diagnostic agents European Patent 1495031 A1; 2005
  • Issa S, Walchshofer N, Kassab I, et al. Synthesis and antiproliferative activity of oxazinocarbazole and N,N-bis(carbazolylmethyl)amine derivatives. Eur J Med Chem 2010;45:2567–77
  • Olgen S, Götz C, Jose J. Synthesis and biological evaluation of 3-(substituted-benzylidene)-1,3-dihydro-indolin derivatives as human protein kinase CK2 and p60(c-Src) tyrosine kinase inhibitors. Biol Pharm Bull 2007;30:715–18
  • Gratz A, Götz C, Jose J. A CE-based assay for human protein kinase CK2 activity measurement and inhibitors screening. Electrophoresis 2010;31:634–40
  • Lacaze N, Gombaud-Saintonge G, Lanotte M. Conditions controlling long-term proliferation of Brown Norway rat promyelocytic leukemia in vitro: primary growth stimulation by microenvironment and establishment of an autonomous Brown Norway ‘leukemic stem cell line'. Leuk Res 1983;8:145–54
  • Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard. 8th ed. Document M07-A8. Wayne (PA): CLSI; 2009
  • Desjardin RE, Canfield CJ, Haynes JD, Chulay JD. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother 1979;16:710–18
  • Farenc C, Fabreguette JR, Bressolle F. Pk-fit: a pharmacokinetic/pharmacodynamic and statistical data analysis software. Comput Biomed Res 2000;33:315–30
  • Arnaud O, Boumendjel A, Géze A, et al. The acridone derivative MBLI-87 sensitizes breast cancer resistance protein-expressing xenografts to irinotecan. Eur J Cancer 2011;47:640–8
  • Compain-Batissou M, Latreche D, Gentili J, et al. Synthesis and Diels-Alder reactivity of ortho-carbazolequinones. Chem Pharm Bull 2004;52:1114–16
  • Poumaroux A, Bouaziz Z, Fillion H. Regiospecific hetero Diels-Alder synthesis of pyrido[2,3-b] and pyrido (3,2-b]carbazole-5,11-diones. Heterocycles 1997;45:585–96
  • Bouaziz Z, Ghérardi A, Régnier F, et al. Synthesis of carbazolequinone derivatives as inhibitors of Toxoplasma gondii purine nucleoside phosphorylase. Eur J Org Chem 2002;2002:1834–8
  • Compain-Batissou M, Gentili J, Walchshofer N, et al. Regioselectivity in the 1,3-dipolar cycloaddition reactions of nitrile oxides and organic azides with carbazole-1,4-diones. Heterocycles 2007;71:27–38
  • Issa S, Walchshofer N, Kassab I, et al. Mannich reaction of 5-hydroxy-β-carboline. Application to the synthesis of novel oxazinopyrimidocarboline derivatives. Heterocycles 2008;75:2761–7
  • Ermakova I, Boldyreff B, Issinger OG, Niefind K. Crystal structure of a C-terminal deletion mutant of human protein kinase CK2 catalytic subunit. J Mol Biol 2003;330:925–34
  • Hundsdörfer C, Hemmerling HJ, Götz C, et al. Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors. Bioorg Med Chem 2012;20:2282–9
  • McCormack E, Bruserud O, Gjertsen BT. Animal models of acute myelogenous leukaemia – development, application and future perspectives. Leukemia 2005;19:687–706
  • Huseby S, Gausdal G, Keen TJ, et al. Cyclic AMP induces IPC leukemia cell apoptosis via CRE- and CDK-dependent Bim transcription. Cell Death Dis 2011;2:e237

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