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Eco-friendly synthesis and antiproliferative evaluation of some oxygen substituted diaryl ketones

Bibliographic reference Arenas, Paola ; Peña, Andrés ; Ríos, David ; Benites, Julio ; Muccioli, Giulio ; et. al. Eco-friendly synthesis and antiproliferative evaluation of some oxygen substituted diaryl ketones. In: Molecules, Vol. 18, no. 8, p. 9818-9832 (2013)
Permanent URL http://hdl.handle.net/2078.1/145225
  1. Thompson (1987)
  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, González M., Colonelli Pamela, Vásquez David, Design and Synthesis of Angucyclinone 5-Aza Analogues, 10.1055/s-2006-950254
  12. Valderrama Jaime A., Vásquez David, Design and synthesis of angucyclinone AB-pyrido[2,3-d] pyrimidine analogues, 10.1016/j.tetlet.2007.11.133
  13. 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
  14. Valderrama Jaime A., Ibacache Andrea, Rodriguez Jaime A., Theoduloz Cristina, Benites Julio, Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents, 10.1016/j.ejmech.2011.05.003
  15. Vásquez David R., Verrax Julien, Valderrama Jaime A., Calderon Pedro Buc, Aminopyrimidoisoquinolinequinone (APIQ) redox cycling is potentiated by ascorbate and induces oxidative stress leading to necrotic-like cancer cell death, 10.1007/s10637-011-9661-1
  16. Monsalve, Int. J. Mol. Med., 30, 151 (2012)
  17. Kviecinski M.R., Pedrosa R.C., Felipe K.B., Farias M.S., Glorieux C., Valenzuela M., Sid B., Benites J., Valderrama J.A., Verrax J., Buc Calderon P., Inhibition of cell proliferation and migration by oxidative stress from ascorbate-driven juglone redox cycling in human bladder-derived T24 cells, 10.1016/j.bbrc.2012.03.150
  18. 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
  19. Iribarra Jennyfer, Vásquez David, Theoduloz Cristina, Benites Julio, Ríos David, Valderrama Jaime A., Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones, 10.3390/molecules171011616
  20. 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
  21. Naeimi Hossein, Moradi Leila, Microwave Assisted Direct Ortho-Acylation of Phenol and Naphthol Derivatives by BF3·(C2H5)2O, 10.1246/bcsj.78.284
  22. Trost Berry M., Saulnier Mark G., Regioselectivity in lithiation of t-butyldimethylsiloxy-3, 5-dimethoxybenzene. A synthesis of the trimethyl ether of sophoraflavanone A, 10.1016/s0040-4039(00)61859-2
  23. Crombie Leslie, Jones Raymond C.F., Palmer Christopher J., Synthesis of the insecticidal 1′-acetoxy-mammeins and surangin b, 10.1016/s0040-4039(00)98875-0
  24. Duplais Christophe, Bures Filip, Sapountzis Ioannis, Korn Tobias J., Cahiez Gérard, Knochel Paul, An Efficient Synthesis of Diaryl Ketones by Iron-Catalyzed Arylation of Aroyl Cyanides, 10.1002/anie.200453696
  25. Sartori Giovanni, Casnati Giuseppe, Bigi Franca, Predieri Giovanni, Ortho-coordinated acylation of phenol systems, 10.1021/jo00301a031
  26. Boyer Jessica L., Krum Jodie E., Myers Michael C., Fazal Aleem N., Wigal Carl T., Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes, 10.1021/jo000412q
  27. Klinger Heinr., Kolvenbach Wilh., Die Bildung von Acetohydrochinon aus Acetaldehyd und Benzochinon im Sonnenlicht, 10.1002/cber.189803101220
  28. Patai, Vol. 1, 503 (1974)
  29. Kraus George A., Liu Peng, Benzophenone-mediated conjugate additions of aromatic aldehydes to quinones, 10.1016/0040-4039(94)80102-9
  30. Oelgemöller Michael, Schiel Christian, Fröhlich Roland, Mattay Jochen, The “Photo-Friedel−Crafts Acylation” of 1,4-Naphthoquinones, 10.1002/1099-0690(200208)2002:15<2465::aid-ejoc2465>3.0.co;2-o
  31. Oelgemöller, Spectrum, 18, 28 (2005)
  32. Murphy Brian, Goodrich Peter, Hardacre Christopher, Oelgemöller Michael, Green photochemistry: photo-Friedel–Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids, 10.1039/b913252j
  33. 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
  34. De Leon Fernando, Kalagara Sudhakar, Navarro Ashley A., Mito Shizue, Synthesis of 6-acyl-5,8-quinolinediols by photo-Friedel–Crafts acylation using sunlight, 10.1016/j.tetlet.2013.04.021
  35. Pettit George R., Toki Brian, Herald Delbert L., Verdier-Pinard Pascal, Boyd Michael R., Hamel Ernest, Pettit Robin K., Antineoplastic Agents. 379. Synthesis of Phenstatin Phosphate1a,†, 10.1021/jm970644q
  36. Álvarez Concepción, Álvarez Raquel, Corchete Purificación, Pérez-Melero Concepción, Peláez Rafael, Medarde Manuel, Synthesis and biological activity of naphthalene analogues of phenstatins: Naphthylphenstatins, 10.1016/j.bmcl.2007.03.082
  37. Mosmann Tim, Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays, 10.1016/0022-1759(83)90303-4
  38. Cushman Mark, Nagarathnam Dhanapalan, Gopal D., Chakraborti Asit K., Lin Chii M., Hamel Ernest, Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization, 10.1021/jm00112a036
  39. Pettit George R., Grealish Matthew P., Jung M. Katherine, Hamel Ernest, Pettit Robin K., Chapuis J.-Charles, Schmidt Jean M., Antineoplastic Agents. 465. Structural Modification of Resveratrol:  Sodium Resverastatin Phosphate1, 10.1021/jm010119y
  40. Liou Jing-Ping, Chang Yi-Ling, Kuo Fu-Ming, Chang Chun-Wei, Tseng Huan-Yi, Wang Chiung-Chiu, Yang Yung-Ning, Chang Jang-Yang, Lee Shiow-Ju, Hsieh Hsing-Pang, Concise Synthesis and Structure−Activity Relationships of Combretastatin A-4 Analogues, 1-Aroylindoles and 3-Aroylindoles, as Novel Classes of Potent Antitubulin Agents, 10.1021/jm049802l
  41. Tron Gian Cesare, Pirali Tracey, Sorba Giovanni, Pagliai Francesca, Busacca Sara, Genazzani Armando A., Medicinal Chemistry of Combretastatin A4:  Present and Future Directions, 10.1021/jm0512903
  42. Romagnoli Romeo, Baraldi Pier Giovanni, Carrion Maria Dora, Cara Carlota Lopez, Preti Delia, Fruttarolo Francesca, Pavani Maria Giovanna, Tabrizi Mojgan Aghazadeh, Tolomeo Manlio, Grimaudo Stefania, Di Cristina Antonella, Balzarini Jan, Hadfield John A., Brancale Andrea, Hamel Ernest, Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization, 10.1021/jm070050f
  43. Hu Laixing, Jiang Jian-dong, Qu Jinrong, Li Yan, Jin Jie, Li Zhuo-rong, Boykin David W., Novel potent antimitotic heterocyclic ketones: Synthesis, antiproliferative activity, and structure–activity relationships, 10.1016/j.bmcl.2007.04.048
  44. Ty Nancy, Kaffy Julia, Arrault Alban, Thoret Sylviane, Pontikis Renée, Dubois Joelle, Morin-Allory Luc, Florent Jean-Claude, Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge, 10.1016/j.bmcl.2009.01.062
  45. Ghinet Alina, Rigo Benoît, Hénichart Jean-Pierre, Le Broc-Ryckewaert Delphine, Pommery Jean, Pommery Nicole, Thuru Xavier, Quesnel Bruno, Gautret Philippe, Synthesis and biological evaluation of phenstatin metabolites, 10.1016/j.bmc.2011.08.047
  46. Bogert Marston Taylor, Howells Henry Price, THE CHEMISTRY OF THE ACYL PARA-QUINONES. A CONTRIBUTION TO THE SOLUTION OF THE “PECHMANN DYES” PROBLEM1, 10.1021/ja01365a061
  47. Abdulla Khalid A., Abdul-Rahman Azhar L., Al-Hamdany Ra'Ad, Al-Saigh Zeki Y., Preparation and Light Induced Reactions of Substituted 1,4-Benzoquinone, 10.1002/prac.19823240321