Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities
Twelve new hydroquinones and quinones (4a-c to 7a-c) derived from free or peracetylated bile acids were prepared by a Barton decarboxylation reaction, with subsequent trapping of the resulting free radical by benzoquinone. All new compounds were completely characterized by 2D NMR techniques and scre...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
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2012
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 10277caa a22012737a 4500 | ||
|---|---|---|---|
| 001 | PAPER-9953 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203956.0 | ||
| 008 | 190411s2012 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-83655201253 | |
| 024 | 7 | |2 cas |a doxorubicin, 23214-92-8, 25316-40-9; Antifungal Agents; Antineoplastic Agents; Benzoquinones; Bile Acids and Salts; Doxorubicin, 23214-92-8; Free Radicals; Hydroquinones; Quinones; Steroids; benzoquinone, 106-51-4 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a STEDA | ||
| 100 | 1 | |a Siless, G.E. | |
| 245 | 1 | 0 | |a Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities |
| 260 | |c 2012 | ||
| 270 | 1 | 0 | |m Palermo, J.A.; UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, (1428) Buenos Aires, Argentina; email: palermo@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Blunt, J.W., Copp, B.R., Hu, W.P., Mhg, M., Northcote, P.T., Prinsep, M.R., Marine natural products (2009) Nat Prod Rep, 26, pp. 170-244. , and references therein | ||
| 504 | |a Gordaliza, M., Cytotoxic terpene quinones from marine sponges (2010) Mar Drugs, 8, pp. 2849-2870 | ||
| 504 | |a Minale, L., Riccio, R., Sodano, G., Avarol a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge Dysidea avara (1974) Tetrahedron Lett, 15, pp. 3401-3404 | ||
| 504 | |a Keyzers, R.A., Davies-Coleman, M.T., Anti-inflammatory metabolites from marine sponges (2005) Chemical Society Reviews, 34 (4), pp. 355-365. , DOI 10.1039/b408600g | ||
| 504 | |a Yasuhara-Bell, J., Lu, Y., Marine compounds and their antiviral activities (2010) Antiviral Res, 86, pp. 231-240 | ||
| 504 | |a Sladic, D., Gasic, M.J., Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order dictyoceratida (2006) Molecules, 11 (1), pp. 1-33. , http://www.mdpi.org/molecules/papers/11010001.pdf, DOI 10.3390/11010001 | ||
| 504 | |a Sarma, A.S., Chattopadhyay, P., Synthetic studies of trans-clerodane diterpenoids and congeners: Stereocontrolled total synthesis of (+/-)-avarol (1982) J Org Chem, 47, pp. 1727-1731. , corrected 1982;47:5427 | ||
| 504 | |a An, J., Wiemer, D.F., Stereoselective synthesis of (+)-avarol, (+)-avarone, and some nonracemic analogues (1996) Journal of Organic Chemistry, 61 (25), pp. 8775-8779. , DOI 10.1021/jo961048r, PII S0022326396010481 | ||
| 504 | |a Ling, T., Xiang, A.X., Theodorakis, E.A., Enantioselective total synthesis of avarol and avarone (1999) Angewandte Chemie - International Edition, 38 (20), pp. 3089-3091. , DOI 10.1002/(SICI)1521-3773(19991018)38:20<3089::AID-ANIE3089>3.0. CO;2-W | ||
| 504 | |a Nakamura, M., Kakuda, T., Qi, J., Hirata, M., Shintani, T., Yoshioka, Y., Okamoto, T., Ojika, M., Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family (2005) Bioscience, Biotechnology and Biochemistry, 69 (9), pp. 1749-1752. , http://www.jstage.jst.go.jp/article/bbb/69/9/1749/_pdf, DOI 10.1271/bbb.69.1749 | ||
| 504 | |a Arif, T., Bhosale, J.D., Kumar, N., Mandal, T.K., Bendre, R.S., Lavekar, G.S., Natural products - Antifungal agents derived from plants (2009) J Asian Nat Prod Res, 11, pp. 621-638 | ||
| 504 | |a Ling, T., Poupon, E., Rueden, E.J., Kim, S.H., Theodorakis, E.A., Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction (2002) Journal of the American Chemical Society, 124 (41), pp. 12261-12267. , DOI 10.1021/ja027517q | ||
| 504 | |a Saraiva, M.F., Couri, M.R.C., Le Hyaric, M., De Almeida, M.V., The Barton ester free-radical reaction: A brief review of applications (2009) Tetrahedron, 65, pp. 3563-3572 | ||
| 504 | |a Barton, D.H., Crich, D., Motherwell, W.B., New and improved methods for the radical decarboxylation of acids (1983) Chem Commun, pp. 939-941 | ||
| 504 | |a Chen, W.C., Sheu, J.H., Fang, L.S., Hu, W.P., Sung, P.J., 3α,7α,12α-Triacetoxy-5β-cholanic acid, a steroid from the Formosan soft coral Alcyonium sp. (alcyoniidae) (2006) Nat. Prod. Res., 20, pp. 748-753 | ||
| 504 | |a Sung, P.J., Fang, L.S., Chen, Y.P., Chen, W.C., Hu, W.P., Ho, C.L., 5β-Steroids from the gorgonian coral Junceella fragilis (Ellisellidae) (2006) Biochem Syst Ecol, 34, pp. 64-70 | ||
| 504 | |a Bal De Kier Joffe, E., Puricelli, L.I., Vidal Del, M.C.C., De Lustig, E.S., Characterization of two murine mammary adenocarcinoma tumors with different metastatic ability (1983) Journal of Experimental and Clinical Cancer Research, 2 (2), pp. 151-160 | ||
| 504 | |a (2008) CLSI, Clinical and Laboratory Standards Institute Document M27-A3, 2, pp. 1-25. , 3rd ed. Pennsylvania: Wayne Ed., NCCLS | ||
| 504 | |a Barton, D.H., Bridon, D., Zard, S., The invention of radical chain reactions. Part XIV: A decarboxylative radical addition to quinones (1987) Tetrahedron, 43, pp. 5307-5314 | ||
| 504 | |a Jurd, L., Roitman, J., Wong, R., Quinones and quinone methides - IV: Dimerization reactions of 2-phenylmethyl-5-methoxy-1,4-benzoquinones (1979) Tetrahedron, 35, pp. 1041-1054 | ||
| 504 | |a Mori, K., Tominaga, M., Takigawa, T., Matsui, M., A mild transesterification method (1973) Synth Commun, pp. 790-791 | ||
| 504 | |a Salomon, C., Mata, E., Mascaretti, O., Scope and mechanism of deprotection of carboxylic esters by bis(tributyltin) oxide (1994) J Org Chem, 59, pp. 7259-7266 | ||
| 504 | |a Furlan, R.L.E., Mata, E.G., Mascaretti, O.A., Cleavage of carboxylic esters effected by organotin oxides and hydroxides under classical heating and microwave irradiation. A comparative study (1996) Tetrahedron Letters, 37 (30), pp. 5229-5232. , DOI 10.1016/0040-4039(96)01071-4 | ||
| 520 | 3 | |a Twelve new hydroquinones and quinones (4a-c to 7a-c) derived from free or peracetylated bile acids were prepared by a Barton decarboxylation reaction, with subsequent trapping of the resulting free radical by benzoquinone. All new compounds were completely characterized by 2D NMR techniques and screened for antifungal and cytotoxic activity. One of the new hydroquinones (7b) showed promising results against the human pancreatic ductal carcinoma cell line PANC1, with similar cytotoxic activity as the commercial chemotherapy drug doxorubicin. © 2011 Elsevier Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Umweltbundesamt | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 0608 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP No. 516-2009 | ||
| 536 | |a Detalles de la financiación: We are indebted to Mrs. Alicia Rivelli for expert assistance with cell culture techniques. Research at the University of Buenos Aires was supported by Grants from CONICET (PIP No. 516-2009 ) and UBA ( X163 Programación 2008–2010 ). S.A.Z. thanks ANPCyT for a research Grant ( PICT 0608 ). G.E.S. and M.G.D. thank CONICET for doctoral and postdoctoral fellowships respectively. M.E.K. thanks ANPCyT for a doctoral fellowship. Appendix A | ||
| 593 | |a UMYMFOR - Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, (1428) Buenos Aires, Argentina | ||
| 593 | |a Research Area, Angel H. Roffo Institute of Oncology, University of Buenos Aires, Av. San Martín 5481, (C1417DTB), Buenos Aires, Argentina | ||
| 593 | |a Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000)-Rosario, Argentina | ||
| 690 | 1 | 0 | |a BARTON DECARBOXYLATION |
| 690 | 1 | 0 | |a BENZOQUINONE |
| 690 | 1 | 0 | |a BILE ACIDS |
| 690 | 1 | 0 | |a CYTOTOXIC ACTIVITY |
| 690 | 1 | 0 | |a QUINONES |
| 690 | 1 | 0 | |a 23 HYDROQUINOYL 3ALPHA HYDROXY 24 NOR 5BETA CHOLANE |
| 690 | 1 | 0 | |a BENZOQUINONE DERIVATIVE |
| 690 | 1 | 0 | |a BILE ACID |
| 690 | 1 | 0 | |a DOXORUBICIN |
| 690 | 1 | 0 | |a HYDROQUINONE DERIVATIVE |
| 690 | 1 | 0 | |a QUINONE DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ADDITION REACTION |
| 690 | 1 | 0 | |a ANTIFUNGAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CANCER CELL CULTURE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DECARBOXYLATION |
| 690 | 1 | 0 | |a DRUG CYTOTOXICITY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a HUMAN CELL |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PANCREAS CARCINOMA |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENTS |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENTS |
| 690 | 1 | 0 | |a BENZOQUINONES |
| 690 | 1 | 0 | |a BILE ACIDS AND SALTS |
| 690 | 1 | 0 | |a CANDIDA ALBICANS |
| 690 | 1 | 0 | |a CARCINOMA, PANCREATIC DUCTAL |
| 690 | 1 | 0 | |a CELL LINE, TUMOR |
| 690 | 1 | 0 | |a CELL SURVIVAL |
| 690 | 1 | 0 | |a DECARBOXYLATION |
| 690 | 1 | 0 | |a DOXORUBICIN |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a FREE RADICALS |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a HYDROQUINONES |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a PANCREATIC NEOPLASMS |
| 690 | 1 | 0 | |a QUINONES |
| 690 | 1 | 0 | |a STEROIDS |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 700 | 1 | |a Knott, M.E. | |
| 700 | 1 | |a Derita, M.G. | |
| 700 | 1 | |a Zacchino, S.A. | |
| 700 | 1 | |a Puricelli, L. | |
| 700 | 1 | |a Palermo, J.A. | |
| 773 | 0 | |d 2012 |g v. 77 |h pp. 45-51 |k n. 1-2 |p Steroids |x 0039128X |w (AR-BaUEN)CENRE-577 |t Steroids | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.steroids.2011.09.012 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_0039128X_v77_n1-2_p45_Siless |y Handle |
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