User menu

Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones

Bibliographic reference Valderrama, Jaime A. ; Cabrera, Mónica ; Benites, Julio ; Ríos, David ; Inostroza-Rivera, Ricardo ; et. al. Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones. In: R S C Advances : an international journal to further the chemical sciences, Vol. 7, no.40, p. 24813-24821 (2017)
Permanent URL http://hdl.handle.net/2078.1/185913
  1. R. H.Thompson, Naturally Occurring Quinones IV: Recent Advances, Blackie Academic & Professional, London, UK, 4th edn, 1997
  2. Maruyama Kazuhiro, Naruta Yoshinori, SYNTHESES OF α- AND β-LAPACHONES AND THEIR HOMOLOGUES BY WAY OF PHOTOCHEMICAL SIDE CHAIN INTRODUCTION TO QUINONE, 10.1246/cl.1977.847
  3. Uno Hidemitsu, Allylation of 2-alkanoyl 1,4-quinones with allylsilanes and allylstannanes. Efficient synthesis of pyranonaphthoquinone antibiotics, 10.1021/jo00353a015
  4. Brimble Margaret A., Lynds Sara M., A short synthesis of deoxyfrenolicin, 10.1039/p19940000493
  5. Kraus George A., Maeda Hiroshi, A direct preparation of 1,4-benzodiazepines. The synthesis of medazepam and related compounds via a common intermediate, 10.1016/0040-4039(94)88461-7
  6. Waske Prashant A., Mattay Jochen, Oelgemöller Michael, Photoacylations of 2-substituted 1,4-naphthoquinones: a concise access to biologically active quinonoid compounds, 10.1016/j.tetlet.2005.12.060
  7. Valderrama Jaime A, Pessoa-Mahana David, Tapia Ricardo A, Rojas de Arias Antonieta, Nakayama Héctor, Torres Susana, Miret Jorge, Ferreira Marı́a Elena, Studies on quinones. Part 34: The reaction of styrene with activated 1,4-benzoquinones: access to potential antiprotozoal pyranobenzoquinones, 10.1016/s0040-4020(01)00860-2
  8. Valderrama Jaime A., Benites Julio, Cortés Manuel, Pessoa-Mahana David, Prina Eric, Fournet Alain, Studies on quinones. Part 35: Access to antiprotozoal active euryfurylquinones and hydroquinones, 10.1016/s0040-4020(01)01186-3
  9. Valderrama Jaime A., Zamorano Carlos, González M. Florencia, Prina Eric, Fournet Alain, Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones, 10.1016/j.bmc.2005.04.041
  10. Valderrama Jaime A., González M. Florencia, Pessoa-Mahana David, Tapia Ricardo A., Fillion Houda, Pautet Felix, Rodriguez Jaime A., Theoduloz Cristina, Schmeda-Hirschmann Guillermo, Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones☆, 10.1016/j.bmc.2006.03.008
  11. Valderrama Jaime A., Vásquez David, Design and synthesis of angucyclinone AB-pyrido[2,3-d] pyrimidine analogues, 10.1016/j.tetlet.2007.11.133
  12. Vásquez David, Rodríguez Jaime A., Theoduloz Cristina, Calderon Pedro Buc, Valderrama Jaime A., Studies on quinones. Part 46. Synthesis and in vitro antitumor evaluation of aminopyrimidoisoquinolinequinones, 10.1016/j.ejmech.2010.08.040
  13. Delgado Virginia, Ibacache Andrea, Theoduloz Cristina, Valderrama Jaime A., Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones, 10.3390/molecules17067042
  14. Schäfer Wolfram, Aguado Antonio, Sezer Utku, A New Method of Preparing Heterocyclic Quinones, 10.1002/anie.197104061
  15. Pardo Mercedes, Joos Karlheinz, Schäfer Wolfram, Über die oxidative Aminierung von 1′,4′-Dihydroxy-2′-acetonaphthon, 10.1002/jlac.197919790411
  16. Rios David, Benites Julio, A. Valderrama Jaime, Farias Mirelle, C. Pedrosa Rozangela, Verrax Julien, Buc Calderon Pedro, Biological Evaluation of 3-Acyl-2-Arylamino-1,4-Naphthoquinones as Inhibitors of Hsp90 Chaperoning Function, 10.2174/156802612804910188
  17. Buff Heiko, Kuckländer Uwe, Reaction of N-Methyl-hydrazones as Azaenamines with Quinones, 10.1016/s0040-4020(00)00185-x
  18. Allen George Rodger, Weiss Martin J., Behavior of 2-carbomethoxy- and 2-acetyl-1,4-benzoquinone in the Nenitzescu indole syntheses, 10.1021/jo01265a037
  19. Valderrama Jaime, González M., Colonelli Pamela, Vásquez David, Design and Synthesis of Angucyclinone 5-Aza Analogues, 10.1055/s-2006-950254
  20. Valderrama Jaime A., Ríos David, Muccioli Giulio G., Buc Calderon Pedro, Brito Iván, Benites Julio, Hetero-annulation reaction between 2-acylnaphthoquinones and 2-aminobenzothiazoles. A new synthetic route to antiproliferative benzo[g]benzothiazolo[2,3-b]quinazoline-7,12-quinones, 10.1016/j.tetlet.2015.07.034
  21. Ríos David, Benites Julio, Torrejón Felipe, Theoduloz Cristina, Valderrama Jaime A., Synthesis and in vitro antiproliferative evaluation of 3-acyl-2-arylamino-1,4-naphthoquinones, 10.1007/s00044-014-0991-3
  22. Farias, Mol. Med. Rep., 10, 405 (2014)
  23. Kyle Hadden M., Hill Stephanie A., Davenport Jason, Matts Robert L., Blagg Brian S.J., Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold, 10.1016/j.bmc.2008.11.064
  24. Lisboa Cinthia da S., Santos Vanessa G., Vaz Boniek G., de Lucas Nanci C., Eberlin Marcos N., Garden Simon J., C−H Functionalization of 1,4-Naphthoquinone by Oxidative Coupling with Anilines in the Presence of a Catalytic Quantity of Copper(II) Acetate, 10.1021/jo200354u
  25. Patil Shivaputra, Patil Renukadevi, Miller Duane, Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles, 10.2174/138527208784567223
  26. Bernier Jean Luc, Henichart Jean Pierre, Vaccher Claude, Houssin Raymond, Condensation of p-benzoquinone with 4-cyano- and 4-nitroanilines. An extension of the Nenitzescu reaction, 10.1021/jo01296a030
  27. Dotzauer Bernd, Grünert Renate, Bednarski Patrick J., Lanig Harald, Landwehr Jens, Troschütz Reinhard, 2,4-Diamino-9H-pyrimido[4,5-b]indol-5-ols: Synthesis, in vitro cytotoxic activity, and QSAR investigations, 10.1016/j.bmc.2006.06.051
  28. Hohenberg P., Kohn W., Inhomogeneous Electron Gas, 10.1103/physrev.136.b864
  29. R. G.Parr and W.Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, USA, 1989
  30. SCHÄFER Wolfram, MOORE Harold W., AGUADO Antonio, Synthesen des 2,1-Benzoxazol-4,7-chinon-Systems, 10.1055/s-1974-23226
  31. Mosmann Tim, Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays, 10.1016/0022-1759(83)90303-4
  32. Benites Julio, Rios David, Díaz Pilar, Valderrama Jaime A., The solar-chemical photo-Friedel–Crafts heteroacylation of 1,4-quinones, 10.1016/j.tetlet.2010.11.149
  33. Kobayashi Kazuhiro, Suzuki Masayoshi, Takeuchi Hiroyasu, Konishi Atsushi, Sakurai Hideo, Suginome Hiroshi, Photoinduoed molecular transformations. Part 146. Photoacylation and photoalkylation of 2-arylamino- and 2-alkylamino-1,4-naphthoquinones, 10.1039/p19940001099
  34. Becke Axel D., Density‐functional thermochemistry. III. The role of exact exchange, 10.1063/1.464913
  35. Lee Chengteh, Yang Weitao, Parr Robert G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, 10.1103/physrevb.37.785
  36. Miehlich Burkhard, Savin Andreas, Stoll Hermann, Preuss Heinzwerner, Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr, 10.1016/0009-2614(89)87234-3
  37. Vosko S. H., Wilk L., Nusair M., Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, 10.1139/p80-159
  38. Tomasi Jacopo, Mennucci Benedetta, Cammi Roberto, Quantum Mechanical Continuum Solvation Models, 10.1021/cr9904009