Aminación reductiva del 4,5-dimetoxi-9,10-dioxo-9,10-dihidroantraceno-2-carbaldehído derivado de aloe-emodin
Resumo
La aminación reductiva para obtener aminas derivadas del carbaldehído del aloe-emodin 1,8-O-protegido empleando diferentes condiciones y agentes reductores es reportada en este artículo. El aldehído fue obtenido con buen rendimiento usando dióxido de manganeso como agente oxidante. De igual manera, se reporta la síntesis de nuevas iminas derivadas de dicho aldehído con buenos rendimientos. Usando borohidruro de sodio en metanol, como agente reductor para la aminación reductiva, se obtuvieron los mejores resultados y las condiciones fueron ajustadas para incrementar el porciento de conversión hasta un 59 % del producto deseado. Se obtuvieron los mismos resultados partiendo del aldehído o de la imina, usando el procedimiento indirecto o paso a paso, respectivamente.
Palabras clave: aloe-emodin, aminación reductiva, imina, amina, borohidruro de sodio
Referências
CARCASONA, A.; GRIMMINGER, W.; HIETALA, P.; ZAESKE, H.; WITTHOHN, K. "Method of preparing Diacetyl Rhein". Madaus AG. Germany. US005393898A. 1995-02-28
MITSCHER, L. A. "Anthracycline synthesis". University of Kansas Endowment Association. USA. US4215062 A. 1980-07-29
LIN, H.-D.; LI, K.-T.; DUAN, Q.-Q.; CHEN, Q.; TIAN, S.; CHU, E. S. M.; BAI, D.-Q. "The effect of aloe-emodin-induced photodynamic activity on the apoptosis of human gastric cancer cells: A pilot study". Oncology Lett. 2017, 13, 3431-3436, ISSN 1792-1082.
CHANG, X.; ZHAO, J.; TIAN, F.; JIANG, Y.; LU, J.; MA, J.; ZHANG, X.; JIN, G.; HUANG, Y.; DONG, Z.; LIU, K.; DONG, Z. "Aloe-emodin suppresses esophageal cancer cell TE1 proliferation by inhibiting AKT and ERK phosphorylation". Oncology Lett. 2016, 12, 2232-2238, ISSN 1792-1082.
THIMMEGOWDA, N. R.; PARK, C.; SHWETHA, B.; SAKCHAISRI, K.; LIU, K.; HWANG, J.; LEE, S.; JEONG, S. J.; SOUNG, N. K.; JANG, J. H.; RYOO, I.-J.; AHN, J. S.; ERIKSON, R. L.; KIM, B. Y. "Synthesis and Antitumor Activity of Natural Compound Aloe Emodin Derivatives", Chem Biol Drug Des. 2015, 85, 638–644, ISSN:1747-0285.
YAO, G.-Y.; YE, M.-Y.; HUANG, R.-Z.; LI, Y.-J.; PAN, Y.-M.; XU, Q.; LIAO, Z.-X.; WANG, H.-S. "Synthesis and antitumor activities of novel rhein -aminophosphonates conjugates", Bioorg Med Chem Lett. 2014, 24, 501–507, ISSN: 0960-894X.
HUANG, P.-H.; HUANG, C.-Y.; CHEN, M.-C.; LEE, Y.-T.; YUE, C.-H.; WANG, H.-Y.; LIN, H. "Emodin and Aloe-Emodin Suppress Breast Cancer Cell Proliferation through ER Inhibition", Evidence-Based Complementary and Alternative Medicine. 2013, 2013, (Article ID 376123), ISSN: 1741-4288.
YANG, X.; SUN, G.; YANG, C.; WANG, B. "Novel Rhein Analogues as Potential Anticancer Agents". ChemMedChem. 2011, 6, 2294 – 2301, ISSN: 1860-7187.
PECERE, T.; GAZZOLA, M. V.; MUCIGNAT, C.; PAROLIN, C.; VECCHIA, F. D.; CAVAGGIONI, A.; BASSO, G.; DIASPRO, A.; SALVATO, B.; CARLI, M.; PALÙ, G. "Aloe-emodin Is a New Type of Anticancer Agent with Selective Activity against Neuroectodermal Tumors", Cancer Res. 2000, 60, 2800–2804, ISSN: 1538-7445.
DIVYA, G.; PANONNUMMAL, R.; GUPTA, S.; JAYAKUMAR, R.; SABITHA, M. "Acitretin and Aloe-emodin loaded chitin nanogel for the treatment of psoriasis", Eur J Pharm Biopharm. 2016, 107, 97-109, ISSN: 0939-6411.
AGARWAL, S. K.; SINGH, S. S.; VERMA, S.; KUMAR, S. "Antifungal activity of anthraquinone derivatives from Rheum emodi", J Ethnopharm. 2000, 72, 43–46, ISSN: 0378-8741.
NG, Y. C.; KIM, Y. W.; RYU, S.; LEE, A.; LEE, J.-S.; SONG, M. J. "Suppression of norovirus by natural phytochemicals from Aloe vera and Eriobotryae Folium". Food Control. 2017, 73, 1362-1370, ISSN: 0956-7135.
LI, S.-W.; YANG, T.-C.; LAI, C.-C.; HUANG, S.-H.; LIAO, J.-M.; WAN, L.; LIN, Y.-J.; LIN, C.-W. "Antiviral activity of aloe-emodin against influenza A virus via galectin-3 up-regulation". Eur J Pharmac. 2014, 738, 125–132, ISSN: 0014-2999.
BARNARD, D. L.; HUFFMAN, J. H.; MORRIS, J. L. B.; WOOD, S. G.; HUGHES, B. G.; SIDWELL, R. W. "Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus". Antiviral Res. 1992, 17, 63-77, ISSN: 0166-3542.
DAI, Y.; HARINANTENAINA, L.; BOWMAN, J. D.; FONSECA, I. O. D.; BRODIE, P. J.; GOETZ, M.; CASSERA, M. B.; KINGSTON, D. G. I. "Isolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure–activity relationships of related compounds". Bioorg Med Chem. 2014, 22, 269–276, ISSN: 0968-0896.
PILLAY, A. Synthesis and Biological Activity of Aloin Derivatives. Master Thesis. University of KwaZulu-Natal, Pietermaritzburg, South Africa, 2008
CUI, X.-R.; TAKAHASHI, K.; SHIMAMURA, T.; KOYANAGI, J.; KOMADA, F.; SAITO, S. "Preparation of 1,8-Di-O-alkylaloe-emodins and 15-Amino-, 15-Thiocyano-, and 15-Selenocyanochrysophanol Derivatives from Aloe-Emodin and Studying Their Cytotoxic Effects". Chem Pharm Bull. 2008, 56, (4), 497—503, ISSN: 1347-5223.
KOYAMA, M.; TAKAHASHI, K.; CHOU, T.-C.; DARZYNKIEWICZ, Z.; KAPUSCINSKI, J.; KELLY, T. R.; WATANABE, K. A. "Intercalating Agents with Covalent Bond Forming Capability. A Novel Type of Potential Anticancer Agents. 2.1 Derivatives of Chrysophanol and Emodin". J Med Chem. 1989, 32, 1594-1599, ISSN: 0022-2623.
HANESSIAN, S.; GUESNE, S.; RIBER, L.; MARIN, J.; BENOIST, A.; MENNECIER, P.; RUPIN, A.; VERBEUREN, T. J.; DE NANTEUIL, G. "Targeting ACE and ECE with dual acting inhibitors". Bioorg Med Chem Lett. 2008, 18, (3), 1058-1062, ISSN: 0960-894X.
SHI, D.-H.; HUANG, W.; LI, C.; WANG, L.-T.; WANG, S.-F. "Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors", Bioorg Med Chem. 2013, 21, 1064–1073, ISSN: 0968-0896.
ABDEL-MAGID, A. F.; MARYANOFF, C. A.; CARSON, K. G. "Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride". Tetrahedron Lett. 1990, 31, (39), 5595-5598, ISSN: 0040-4039.
ABDEL-MAGID, A. F.; CARSON, K. G.; HARRIS, B. D.; MARYANOFF, C. A.; SHAH, R. D. "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures". J Org Chem. 1996, 61, 3849-3862, ISSN: 1520-6904.
MATTSON, R. J.; PHAM, K. M.; LEUCK, D. J.; COWEN, K. A. "An improved method for reductive alkylation of amines using titanium(IV) isopropoxide and sodium cyanoborohydride". J Org Chem. 1990, 55, (8), 2552-2554, ISSN: 1520-6904.
BANDGAR, B. P.; NIKAT, S. M.; WADGAONKAR, P. P. "The Reduction of Aromatic Oximes to Amines with Borohydride Exchange Resin-Nickel Acetate System". Synth Comm. 1995, 25, (6), 863-869, ISSN: 1532-2432.
BRUSSEE, J.; BENTHEM, R. A. T. M. V.; KRUSE, C. G.; GEN, A. V. D. "Magnesium ion mediated stereospecific formation of N-substituted ethanolamines during reductive amination". Tetrahedron: Asymmetry. 1990, 1, (3), 163-166, ISSN: 0957-4166.
SHI, D.-H.; HUANG, W.; LI, C.; LIU, Y.-W.; WANG, S.-F. "Design, synthesis and molecular modeling of aloe-emodin derivatives as potent xanthine oxidase inhibitors". Eur J Med Chem. 2014, 75, 289-296, ISSN: 0223-5234.
LIU, J.; WU, F.; CHEN, C. "Design and synthesis of aloe-emodin derivatives as potent anti-tyrosinase, antibacterial and anti-inflammatory agents". Bioorg Med Chem Lett. 2015, 25, 5142–5146, ISSN: 0960-894X.
ROY, B. N.; SING, G. P.; LATHI, P. S. "Eco-friendly method for catalytic aerial oxidation of Aloe-emodin to rheinal: An intermediate for diacerein". Indian J Chem. 2012, 51B, 988-991, ISSN: 0975-0983.
ZHANG, Y.; ZHANG, C.; WU, W. "Preparation of rhein from aloe-emodin in nonmetallicoxidate medium". Dalian Gongye Daxue Xuebao. 2009, 28, (1), 13-16.
YANG-MING, Z.; DIANGEN, Z.; WENJIE, W.; BO, W. "Technique for preparing diacerein by two-step oxidation process". SHANGHAI AUSPURE BIOTECHNOLOGY CO LTD; NORTHCAROLINA CHEMLABS SHANGHAI CN101104583B.
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