Highly Efficient Synthesis of 1,3-Dihydroxy-2-carboxycarbazole and Its Neuroprotective Effects

ACS Medicinal Chemistry Letters

Volumn 6, Issue 8, 2015, Pages 894-897

  Liu, Kai ^a   Zhang, Shijun ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

antioxidant; A oligomers; Carbazole derivative; Meldrum's acid; neuroprotection; synthesis

Indexed keywords

1,3 DIHYDROXY 2 CARBOXYCARBAZOLE; AMYLOID BETA PROTEIN; AMYLOID PRECURSOR PROTEIN; CARBAZOLE DERIVATIVE; CURCUMIN; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; NEUROPROTECTION; OLIGOMERIZATION; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN AGGREGATION;

EID: 84938941381     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00158     Document Type: Article

References (27)

1. Alzheimer's Association 2013 Alzheimer's disease facts and figures Alzheimer's Dementia 2013, 9, 208-245 10.1016/j.jalz.2013.02.003
2. Hardy, J.; Selkoe, D. J. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics Science 2002, 297, 353-356 10.1126/science.1072994
3. Kirkitadze, M. D.; Bitan, G.; Teplow, D. B. Paradigm shifts in Alzheimer's disease and other neurodegenerative disorders: the emerging role of oligomeric assemblies J. Neurosci. Res. 2002, 69, 567-577 10.1002/jnr.10328
4. Walsh, D. M.; Selkoe, D. J. A beta oligomers-a decade of discovery J. Neurochem. 2007, 101, 1172-1184 10.1111/j.1471-4159.2006.04426.x
5. Pi, L.; Xia, H.; Liu, J.; Shenoy, A. K.; Hauswirth, W. W.; Scott, E. W. Role of connective tissue growth factor in the retinal vasculature during development and ischemia Invest. Ophthalmol. Visual Sci. 2011, 52, 8701-8710 10.1167/iovs.11-7870
6. Bush, A. I. Drug development based on the metals hypothesis of Alzheimer's disease J. Alzheimers Dis. 2008, 15, 223-240
7. Zhu, X.; Su, B.; Wang, X.; Smith, M. A.; Perry, G. Causes of oxidative stress in Alzheimer disease Cell. Mol. Life Sci. 2007, 64, 2202-2210 10.1007/s00018-007-7218-4
8. Eckert, G. P.; Renner, K.; Eckert, S. H.; Eckmann, J.; Hagl, S.; Abdel-Kader, R.; Kurz, M. C.; Leuner, K.; Muller, W. E. Mitochondrial dysfunction - a pharmacological target in Alzheimer's disease Mol. Neurobiol. 2012, 46, 136-150 10.1007/s12035-012-8271-z
9. Graebe, C.; Glazer, C. Ueber Carbazol Justus Liebigs Ann. Chem. 1872, 163, 343-360 10.1002/jlac.18721630305
10. Knölker, H. J.; Reddy, K. R. Isolation and synthesis of biologically active carbazole alkaloids Chem. Rev. 2002, 102, 4303-4428 10.1021/cr020059j
11. Schmidt, A. W.; Reddy, K. R.; Knölker, H. J. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids Chem. Rev. 2012, 112, 3193-3328 10.1021/cr200447s
12. Roy, J.; Jana, A. K.; Mal, D. Recent trends in the synthesis of carbazoles: an update Tetrahedron 2012, 68, 6099-6121 10.1016/j.tet.2012.05.007
13. Lim, B. Y.; Choi, M. K.; Cho, C. G. Acid-catalyzed condensation of 2,2′-diamino-1,1′-biaryls for the synthesis of benzo[c]carbazoles Tetrahedron Lett. 2011, 52, 6015-6017 10.1016/j.tetlet.2011.09.001
14. Preston, R. W. G.; Tucker, S. H.; J. Cameron, M. L. The Graebe-Ullmann synthesis of carbazole derivatives. Preparation and synthesis of 1-nitrocarbazole J. Chem. Soc. 1942, 500-504 10.1039/jr9420000500
15. Liu, Z.; Larock, R. C. Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization Tetrahedron 2007, 63, 347-355 10.1016/j.tet.2006.10.071
16. Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H. Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. The Double N-Arylation of Primary Amines: Toward Multisubstituted Carbazoles with Unique Optical Properties Angew. Chem., Int. Ed. 2003, 42, 2051-2053 10.1002/anie.200250648
17. Crich, D.; Rumthao, S. Synthesis of carbazomycin B by radical arylation of benzene Tetrahedron 2004, 60, 1513-1516 10.1016/j.tet.2003.12.015
18. Ivanov, A. S. Meldrum's acid and related compounds in the synthesis of natural products and analogs Chem. Soc. Rev. 2008, 37, 789-811 10.1039/b716020h
19. Lipson, V. V.; Gorobets, N. Y. One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives Mol. Diversity 2009, 13, 399-419 10.1007/s11030-009-9136-x
20. Fillion, E.; Fishlock, D. Convenient access to polysubstituted 1-indanones by Sc(OTf)3-catalyzed intramolecular Friedel-Crafts acylation of benzyl meldrum's acid derivatives Org. Lett. 2003, 5, 4653-4656 10.1021/ol035817m
21. Xu, F.; Armstrong, J. D.; Zhou, G. X.; Simmons, B.; Hughes, D.; Ge, Z.; Grabowski, E. J. Mechanistic evidence for an α-oxoketene pathway in the formation of β-ketoamides/esters via Meldrum's acid adducts J. Am. Chem. Soc. 2004, 126, 13002-13009 10.1021/ja046488b
22. Liu, K.; Gandhi, R.; Chen, J.; Zhang, S. Bivalent ligands targeting multiple pathological factors involved in Alzheimer's disease ACS Med. Chem. Lett. 2012, 3, 942-946 10.1021/ml300229y
23. Rana, S.; Hong, H. S.; Barrigan, L.; Jin, L. W.; Hua, D. H. Syntheses of tricyclic pyrones and pyridinones and protection of Aβ-peptide induced MC65 neuronal cell death Bioorg. Med. Chem. Lett. 2009, 19, 670-674 10.1016/j.bmcl.2008.12.060
24. Sopher, B. L.; Fukuchi, K.; Smith, A. C.; Leppig, K. A.; Furlong, C. E.; Martin, G. M. Cytotoxicity mediated by conditional expression of a carboxyl-terminal derivative of the beta-amyloid precursor protein Mol. Brain Res. 1994, 26, 207-217 10.1016/0169-328X(94)90092-2
25. Reinke, A. A.; Gestwicki, J. E. Structure-activity relationships of amyloid beta-aggregation inhibitors based on curcumin: influence of linker length and flexibility Chem. Biol. Drug Des. 2007, 70, 206-215 10.1111/j.1747-0285.2007.00557.x
26. Sopher, B. L.; Fukuchi, K. I.; Kavanagh, T. J.; Furlong, C. E.; Martin, G. M. Neurodegenerative mechanisms in Alzheimer's disease Mol. Chem. Neuropathol. 1996, 29, 153-167 10.1007/BF02814999
27. van den Berg, R.; Haenen, G. R.; van den Berg, H.; Bast, A. A. L. T. Applicability of an improved Trolox equivalent antioxidant capacity (TEAC) assay for evaluation of antioxidant capacity measurements of mixtures Food Chem. 1999, 66, 511-517 10.1016/S0308-8146(99)00089-8