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Paulo Marcos Donate

Associate Professor, FFCLRP-USP, since 1993

B. Sc. (1978)
Ph. D. (1984)
Postdoctoral fellow (France, 1986-1990)
Research Chemist (Rhodia S.A., 1982-1993)
"Livre-Docente" (2000)

Research: Synthesis and Study of Natural Products with biological activity

Our main area of research is the synthesis of natural products which present several kinds of biological activities and pharmaceutical interest. A number of targets are currently being pursued, including derivatives of lignan lactones, that are natural products which occur in several plants and show a wide range of biological activities, as well as several carotenoids and flavonoids. In order to carry out efficient syntheses of the required target molecules it is often necessary to develop new synthetic methodology, including the utilisation of organometallic reagents and chiral catalysts.

 

 

Selected Publications

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Synthesis
bulletP. M. Donate, R. da Silva, M. G. Constantino, S. Pedersoli, "Synthesis of gamma-butyrolactones: beta-hydroxymethyl, beta-methylene and cyclopropane derivatives", Synthetic Communications 1999, 29, 2923-2936.
bulletM. G. Constantino, P. M. Donate, D. Frederico, T. V. Carvalho, L. E. Cardoso, J. Zukerman-Schpector, "Ring contraction through epoxide rearrangement: A formal synthesis of Capsorubin", Synthetic Communications 2000, 30, 3327-3340.
bulletP. M. Donate, R. da Silva, G. V. J. da Silva, C. Alemán, "Synthesis of benzofuranofuran derivatives model of natural products", Synthetic Communications 2001, 31, 141-150.
bulletP. M. Donate, D. Frederico, R. da Silva, M. G. Constantino, G. Del Ponte, P. S. Bonatto, "Asymmetric synthesis of gamma-butyrolactones by enantioselective hydrogenation of butenolides", Tetrahedron: Asymmetry 2003, 14, 3253-3256.
bulletD. Frederico, E. S. Bronze, M. I. Sairre, M. G. Constantino, P. M. Donate, "A short and efficient synthesis of crocetin-dimethylester and crocetindial", Journal of the Organic Chemistry 2003, 68, 9126-9128.
bulletR. da Silva, G. H. B. Souza, A. A. Silva Filho, V. A. Souza, A. C. Pereira, V. A. Royo, M. L. A. Silva, P. M. Donate, A. L. M. Araújo, J. C. T. Carvalho, J. K. Bastos, "Synthesis and biological activity evaluation of lignan lactones derived from (-)-cubebin", Bioorganic & Medicinal Chemistry Letters 2005, 15, 1033-1037.
bulletM. I. Sairre, E. S. Bronze-Uhle, P. M. Donate, "Niobium(V) oxide: A new and efficient catalyst for the transesterification of beta-keto esters", Tetrahedron Letters 2005, 46, 2705-2708.
bulletR. da Silva, P. M. Donate, G. V. J. da Silva, S. Pedersoli, C. Alemán, "Racemic synthesis of 1,2-secomicrominutinin", Journal of the Brazilian Chemical Society 2005, 16, 626-633.
bulletE. S. B. Uhle, M. I. Sairre, P. M. Donate, D. Frederico, "Enantioselective hydrogenation of 4-(hydroxymethyl)-furan-2(5H)-one derivatives", Journal of Molecular Catalysis. A - Chemical 2006, 259, 103-107.
bulletD. Frederico, M. G. Constantino, P. M. Donate, "Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin", Journal of the Brazilian Chemical Society 2009, 20, 888-894.
bulletA. F. Nascimento, M. G. Constantino, P. M. Donate, "Total synthesis of aripuanin, a megastigmane from Ficus aripuanensis", Orbital: The Electronic Journal of Chemistry 2012, 4, 253-262.
bullet P. M. Donate, "Green synthesis from biomass", Chemical and Biological Technologies in Agriculture 2014, 1, 1-8.
bullet M. F. Pinatto-Botelho, A. E. M. Crotti, J. M. Souza, L. G. Magalhaes, P. M. Donate, "Microwave assisted synthesis and antileishmanial activity of 3-methoxycarbonyl-gamma-butyrolactone derivatives", Journal of the Brazilian Chemical Society 2014, 25, 1331-1337.
bulletR. S. de Laurentiz, A. Borges, M. L. A. Silva, P. M. Donate, "Convenient synthesis of ketal derivatives from cubebin using Amberlite as heterogeneous catalyst", Chemistry of Natural Compounds 2015, 51, 34-39.
bulletM. F. Pinatto-Botelho, P. M. Donate, "A rapid protocol to synthesize gamma-butyrolactone derivatives via the microwave technique", Current Microwave Chemistry 2015, 2, 83-87.
bullet G. V. Castro, C. M. R. Rocha, V. L. Sanches, P. H. Z. Ribeiro, P. M. Donate, R. S. Laurentiz, I. Polikarpov, M. I. Sairre, "Synthesis of analogues of thyroid hormones: Nuclear receptor modulators", Orbital: The Electronic Journal of Chemistry 2015, 7, 281-291.
bulletA. S. Lazaro, P. H. Z. Ribeiro, M. I. Sairre, P. M. Donate, "New approach to the synthesis of aripuanin", Synthetic Communications 2015, 45, 1374-1378.
bulletE. H. B. Silva, F. S. Emery, G. Del Ponte, P. M. Donate, "Synthesis of some functionalized peptomers via Ugi four-component reaction", Synthetic Communications 2015, 45, 1761-1767.
bulletG. Del Ponte, F. C. Archanjo, L. Y. Watanabe, P. M. Donate, J. M. Campos, "Synthesis of non-aromatic medium and large rings synthesized via phenylnitrenium ions", Arabian Journal of Chemistry 2016, 9, S1878.
bulletD. Previdi, M. E. Rosa, P. M. Donate, "Fast and efficient synthesis of maculalactone derivatives via the microwave technique", Current Microwave Chemistry 2017, 4, 229-237.

 

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Computational and Other Studies
bulletP. M. Donate, G. K. Pereira, S. E. Galembeck, "Electronic structure of hydroxylated derivatives of flavylium cation", Journal of Molecular Structure (Theochem) 1996, 363, 87-96.
bulletP. M. Donate, G. K. Pereira, S. E. Galembeck, "Effects of substitution for hydroxyl in the B-ring of the flavylium cation", Journal of Molecular Structure (Theochem) 1997, 392, 169-179.
bulletP. M. Donate, H. M. Ishiki, S. E. Galembeck, "Electronic structure of chromone and its hydroxylated derivatives on positions 2 and 3", Journal of Molecular Structure (Theochem) 1998, 423, 235-243.
bulletP. M. Donate, E. A. Armelin, C. Aleman, S. E. Galembeck, "Computational studies in aqueous and chloroform solutions of complex solutes: Distinctive effects of the solvent on solutes with small chemical differences", Chemical Physics,  1999, 241, 167-177.
bulletF. M. Lanças, P. M. Donate, A. L. Rezemini, "Upgrading of sugar cane bagasse by thermal processes. 9. Catalytic liquefaction in ethanol", Energy Sources 1999, 21, 299-308.
bulletF. M. Lanças, P. M. Donate, M. A. Ruggiero, "Upgrading of sugar cane bagasse by thermal processes. 10. Catalytic liquefaction in aqueous medium", Energy Sources 1999, 21, 309-318.
bulletC. J. Rocha, P. M. Donate, R. da Silva e M. H. Gehlen, "Time resolved fluorescence spectroscopy of quinine dication free and bound to polymethacrylic acid", Journal of Photochemistry and Photobiology A: Chemistry 1999, 123, 129-136.
bulletC. Aleman, P. M. Donate, R. da Silva, G. V. J. da Silva, "Conformational preferences of 2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran. The chemical modifications drive the pseudorotational preferences", Journal of Organic Chemistry 1999, 64, 5712-5714.
bulletE. A. Armelin, P. M. Donate, S. E. Galembeck, "Effect of the environment on the reactivity of 4'-substituted flavones and isoflavones ", Tetrahedron 2000, 56, 5105-5111.
bulletV. A. Royo, F. F. Santos, V. A. Souza, A. C. Pereira, R. da Silva, A. H. C. Vinholis, P. M. Donate, M. L. A. Silva, S. Albuquerque, J. K. Bastos, "Biological activity evaluation of dibenzylbutyrolactones lignans derivatives against Leishmania braziliensis", Revista Brasileira de Farmacognosia 2003, 13, 18-21.
bulletG. H. B. Souza, A. A. Silva Filho, V. A. Souza, A. C. Pereira, V. A. Royo, M. L. A. Silva, R. da Silva, P. M. Donate, J. C. T. Carvalho, J. K. Bastos, "Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-)-cubebin", Il Farmaco 2004, 59, 55-61.
bullet R. da Silva, V. C. G. Heleno, S. Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. da Silva, "Complete assignment of 1H and 13C NMR data for three aryltetralin lignan lactones", Magnetic Resonance in Chemistry 2004, 42, 985-989.
bulletV. A. Souza, R. da Silva, A. C. Pereira, V. A. Royo, J. Saraiva, M. Montanheiro, G. H. B. Souza, A. A. Silva Filho, M. Grando, P. M. Donate, J. K. Bastos, S. Albuquerque, M. L. A. Silva, "Trypanocidal activity of (-)-cubebin derivatives against free amastigote forms of Trypanosima cruzi", Bioorganic & Medicinal Chemistry Letters 2005, 15, 303-307.
bulletM. R. Guzzo, P. M. Donate, S. Nicolaou, A. E. H. Machado, L. T. Okano, "Study of the complexation of fisetin with cyclodextrins", Journal of Physical Chemistry A 2006, 110, 10545-10551.
bulletV. C. G. Heleno, R. da Silva, S. Pedersoli, S. Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. da Silva, J. L. C. Lopes, "Detailed 1H and 13C NMR structural assignment of three biologically active lignan lactones", Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2006, 63,      234-239.
bulletK. T. Oliveira, V.Lacerda Junior, M. G. Constantino, P. M. Donate, G. V. J. da Silva, T. J. Brocksom, D. Frederico, "Analysis of a cycloheptenone derivative: An experimental and theoretical approach", Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2006, 63, 709-713.
bulletR. da Silva, M. M. Ruas, P. M. Donate, "Complete assignment of 1H and 13C NMR spectral data for arylnaphthalene lactones", Magnetic Resonance in Chemistry 2007, 45, 902-904.
bulletR. Kiralj, M. M. C. Ferreira, P. M. Donate, R. da Silva, S. Albuquerque, "Conformational study of (8 alpha, 8' beta)-bis-(substitued phenyl)-lignano-9,9'-lactones by menas of combined computational database mining, NMR and chemometric approaches", Journal of Physical Chemistry 2007, 111, 6316-6333.
bulletJ. Saraiva, C. Vega, M. Rolon, R. da Silva, M. L. A. Silva, P. M. Donate, J. K. Bastos, S. Albuquerque, A. Gomez-Barrio,  "In vitro and in vivo activity of lignan lactone derivatives against Trypanosima cruzi", Parasitology Research 2007, 100, 791-795.
bulletP. M. Donate, R. da Silva, J. Saraiva, S. Albuquerque, C. Curti, T. N. C. Bianco, J. K. Bastos, M. L. A. Silva, "Trypanocidal structure activity relationship for cis- and trans-methylpluviatolide", Phytochemistry 2008, 69, 1890-1894.
bullet L. Bleicher, R. Aparicio, F. M. Nunes, L. Martinez, S. M. G. Dias, A. C. M. Figueira, M. A. M. Santos, W. H. Venturelli, R. da Silva, P. M. Donate, F. A. R. Neves, J. D. Baxter, P. Webb, M. S. Skaf, I. Polikarpov, "Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms", BMC Structural Biology 2008, 8, 1-13.
bulletA. E. M. Crotti, E. S. B. Uhle, P. G. B. D. Nascimento, P. M. Donate, S. E. Galembeck, R. Vessecchi, N. P. Lopes, "Gas-phase fragmentation of gamma-lactone derivatives by electrospray ionization tandem mass spectrometry", Journal of Mass Spectrometry 2009, 44, 1733-1741.
bulletR. da Silva, J. H. C. Batista, C. S. Maringolo, P. M. Donate, "Complete assignment of 1H and 13C NMR spectral data for 7,7'-dihydroarylnaphthalene lignan lactones", Magnetic Resonance in Chemistry 2009, 47, 523-526.
bulletP. A. R. Pires, M. Imran, C. Loffredo, P. M. Donate, D. Previdi, O. A. El Seoud, "Solvatochromism of 2-(N,N-dimethylamino)-7-nitrofluorene and the natural dye beta-carotene:  Application for the determination of solvent dipolarity and polarizability", Journal of Physical Organic Chemistry 2013, 26, 280-285.
bullet L. F. Nascimento, E. Y. Matsubara, P. M. Donate, J. M. Rosolen, "Catalytic behavior of ruthenium anchored on micronanostructured composite in seletive benzyl alcohol oxidation", Reaction Kinetics, Mechanisms and Catalysis 2013, 110, 471-483.
bullet P. H. Z. Ribeiro, E. Y. Matsubara, J. M. Rosolen, P. M. Donate, R. Gunnella,  "Palladium decoration of hybrid carbon nanotubes/charcoal composite and its catalytic behavior in the hydrogenation of trans-cinnamaldehyde", Journal of Molecular Catalysis. A, Chemical 2015, 410, 34-40.
bullet S. Vaz Junior, P. M. Donate, "Microwave-assisted green production of furfural from D-xylose of sugarcane bagasse", BioResources 2015, 10, 8168-8180.

This page was last updated on 09/15/17