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17 results on '"Rolando A. Spanevello"'

1. Glycomimetic Based Approach toward Selective Carbonic Anhydrase Inhibitors

Author

Andrea Goti, Camilla Matassini, Francesca Cardona, Rolando A. Spanevello, Debora Pratesi, Fabrizio Carta, Andrea Angeli, and Claudiu T. Supuran

Subjects
Gene isoform, CARBONIC ANHYDRASE INHIBITORS, 01 natural sciences, Biochemistry, Glycomimetic, Carbonic anhydrase, Drug Discovery, LEVOGLUCOSENONE, PIPERIDINE IMINOSUGAR, Sugar moiety, SULFONAMIDE, GLYCOMIMETIC, IMINOSUGARS, chemistry.chemical_classification, biology, 010405 organic chemistry, Organic Chemistry, Ciencias Químicas, Carbohydrate moiety, 0104 chemical sciences, Sulfonamide, 010404 medicinal & biomolecular chemistry, Química Orgánica, chemistry, biology.protein, CIENCIAS NATURALES Y EXACTAS
Abstract

The synthesis of selective inhibitors of human carbonic anhydrases (hCAs) is of paramount importance to avoid side effects derived from undesired interactions with isoforms not involved in the targeted pathology, and this was partially addressed with the introduction of a sugar moiety (the so-called "sugar approach"). Since glycomimetics are considered more selective than the parent sugars in inhibiting carbohydrate-processing enzyme, we explored the possibility of further tuning the selectivity of hCAs inhibitors by combining the sulfonamide moiety with a sugar analogue residue. In particular, we report the synthesis of two novel hCAs inhibitors 2 and 3 which feature the presence of a piperidine iminosugar and an additional carbohydrate moiety derived from levoglucosenone (1), a key intermediate derived from cellulose pyrolysis. Biological assays revealed that iminosugar 2 is a very strong inhibitor of the central nervous system (CNS) abundantly expressed hCA VII (KI of 7.4 nM) and showed a remarkable selectivity profile toward this isoform. Interestingly, the presence of levoglucosenone in glycomimetic 3 imparted a strong inhibitory activity toward the tumor associated hCA IX (KI of 35.9 nM). Fil: Pratesi, Debora. Università degli Studi di Firenze; Italia Fil: Matassini, Camilla. Università degli Studi di Firenze; Italia Fil: Goti, Andrea. Università degli Studi di Firenze; Italia Fil: Angeli, Andrea. Università degli Studi di Firenze; Italia Fil: Carta, Fabrizio. Università degli Studi di Firenze; Italia Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Cardona, Francesca. Università degli Studi di Firenze; Italia

Published
2020
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2. International Perspectives on Green and Sustainable Chemistry Education via Systems Thinking

Author

Paulette Gomez, Liliana Mammino, Rolando A. Spanevello, Maria S. Climent-Bellido, Alina M. Balu, Antonio Gomera, Kei Saito, J. Chris Slootweg, Glenn A. Hurst, Jorge G. Ibanez, Rafael Luque, and Synthetic Organic Chemistry (HIMS, FNWI)

Subjects
Latin Americans, 010405 organic chemistry, media_common.quotation_subject, 05 social sciences, 050301 education, Library science, General Chemistry, 01 natural sciences, 0104 chemical sciences, Education, International education, Politics, Excellence, Sustainability, Systems thinking, 0503 education, Curriculum, Inclusion (education), media_common
Abstract

Various international perspectives from selected regions where substantial work is being done on green and sustainable chemistry education emphasize a systems thinking framework. Common to most of the perspectives is the inclusion of more global paradigms involving economic, environmental, political, and social aspects as fundamental issues in the formerly merely technical and scientific discussions, as well as the development of laboratory experiences, training sessions, written materials, discussion meetings, and conferences. We include bird’s eye views from Europe (the Green Chemistry Centre of Excellence at the University of York, United Kingdom; the University of Cordoba, Spain; and the University of Amsterdam, The Netherlands), Latin America (the Universidad Nacional de Rosario, Argentina, and the Universidad Iberoamericana, Mexico), Africa (the University of Venda, South Africa), and Australia (Monash University).

Published
2019
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3. Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies

Author

Gabriela Guillermina Gerosa, Alejandra G. Suárez, Ariel M. Sarotti, Maribel O. Marcarino, and Rolando A. Spanevello

Subjects
ONIOM, 010405 organic chemistry, Chemistry, Organic Chemistry, Rational design, Alkylation, 010402 general chemistry, ORGANOCATALYSTS, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Catalysis, BIOMASS, purl.org/becyt/ford/1 [https], purl.org/becyt/ford/1.4 [https], LEVOGLUCOSENONE, Efficient catalyst, Selectivity, Re engineering, FRIELD-CRAFTS, Friedel–Crafts reaction
Abstract

The discovery of efficient organocatalysts is generally carried out by thorough experimental screening of different candidates. We recently reported an efficient organocatalyst for iminium-ion-based asymmetric Diels-Alder reactions following a rational design approach. This result encouraged us to test this optimal catalyst in the mechanistically related Friedel-Crafts alkylation of indoles, but to our surprise, almost null enantioselectivity was observed. The results did not significantly improve with structurally related catalysts, and a totally unexpected facial selectivity inversion was also noticed. Using DFT calculations by modeling the competing transition structures with ONIOM, we could unravel the origins of those findings, further employed to predict the most efficient catalyst for this new transformation. The computational results were validated experimentally (up to 92:8 er), providing another successful example of a general strategy to accelerate catalyst development which still remains underexplored. Fil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Marcarino, Maribel Oriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2020

4. A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

Author

Alejandra G. Suárez, Rolando A. Spanevello, María Betina Comba, Maria Ines Mangione, and Ariel M. Sarotti

Subjects
010405 organic chemistry, Organic Chemistry, Epoxide, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Medicinal chemistry, Domino, 0104 chemical sciences, Thiosugars, chemistry.chemical_compound, chemistry, Xanthate, Physical and Theoretical Chemistry
Abstract

Fil: Comba, Maria Betina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Rosario. Instituto de Quimica Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquimicas y Farmaceuticas. Instituto de Quimica Rosario; Argentina

Published
2018
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5. Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

Author

María Betina Comba, Rolando A. Spanevello, Maria Ines Mangione, Alejandra G. Suárez, Ariel M. Sarotti, and Yi-hsuan Tsai

Subjects
010405 organic chemistry, Chemistry, Organic Chemistry, Enantioselective synthesis, Biomass, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, Enantiopure drug, Organic chemistry, Physical and Theoretical Chemistry, Cellulose
Abstract

The need to find sustainable alternatives to reduce the dependence on fossil sources has led to significant research efforts on the conversion of biomass into platform chemicals. Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. The selective pyrolytic conversion of cellulose or cellulose-containing materials produces levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

Published
2017
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6. Diels–Alder reaction of two green chiral precursors. Approach to natural product like structures

Author

Leopoldo Suescun, Gonzalo Carrau, Rolando A. Spanevello, German Francisco Giri, Alejandra G. Suárez, Nicolás Veiga, and David Gonzalez

Subjects
Green chemistry, Natural product, 010405 organic chemistry, Organic Chemistry, Diol, 010402 general chemistry, 01 natural sciences, Biochemistry, Cycloaddition, 0104 chemical sciences, Adduct, chemistry.chemical_compound, chemistry, Drug Discovery, Diels alder, Organic chemistry, Cellulose, Diels–Alder reaction
Abstract

Diels–Alder cycloaddition between an enantiomerically pure protected cis-cyclohexadiene diol metabolite and optically pure levoglucosenone derived from cellulose gave rise to complex pentacyclic natural product like structures in a chemically succinct process. The adducts were fully characterized and the observed results were in accord with theoretical calculations performed on the possible course of the reaction.

Published
2016
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7. Design, synthesis and evaluation of novel levoglucosenone derivatives as promising anticancer agents

Author

Alejandra G. Suárez, Javier Girardini, Soledad Cicetti, Yi-hsuan Tsai, Ariel M. Sarotti, Carla M. Borini Etichetti, and Rolando A. Spanevello

Subjects
Stereochemistry, Clinical Biochemistry, Pharmaceutical Science, Antineoplastic Agents, 01 natural sciences, Biochemistry, Structure-Activity Relationship, Cell Line, Tumor, Drug Discovery, Humans, Molecular Biology, Cell Proliferation, Mda mb 231, Dose-Response Relationship, Drug, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Isoxazoles, Triazoles, Bridged Bicyclo Compounds, Heterocyclic, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, Glucose, Design synthesis, Drug Design, Molecular Medicine, Drug Screening Assays, Antitumor
Abstract

A series of levoglucosenone-derived 1,2,3-triazoles and isoxazoles featuring a flexible spacer between the heteroaromatic and anhydropyranose cores have been designed and synthesized following an hetero Michael // 1,3-dipolar cycloaddition path. The use of a design of experiments approach allowed the optimization of the oxa-Michael reaction with propargyl alcohol as nucleophile, a key step for the synthesis of the target compounds. All of the compounds were tested for their anticancer activity on MDA-MB-231 cells, featuring mutant p53. The results highlighted the importance of the introduction of the flexible spacer as well as the higher activity of oxa-Michael isoxazole-derivatives. The most prominent compounds also showed anti-proliferative activities against lung and colon cancer cell lines. The compounds showed enhanced cytotoxic effects in the presence of mutant p53, determined both by endogenous mutant p53 knock down (R280K) and by reintroducing p53 R280K in cells lacking p53 expression.

Published
2020
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8. Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene

Author

Maria Ines Mangione, Gustavo M. Morales, Rolando A. Spanevello, María Victoria Cappellari, Gabriela Lorena Marzari, and Fernando Fungo

Subjects
DENDRIMERIC STRUCTURES, 010405 organic chemistry, Renewable Energy, Sustainability and the Environment, Carbazole, ORGANIC LIGHT-EMITTING DEVICES, Físico-Química, Ciencia de los Polímeros, Electroquímica, TRIPHENYLAMINE, Ciencias Químicas, 010402 general chemistry, Condensed Matter Physics, Triphenylamine, 01 natural sciences, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, chemistry, Polymer chemistry, Materials Chemistry, Electrochemistry, Pyrene, CARBAZOLE, CIENCIAS NATURALES Y EXACTAS
Abstract

The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices. Fil: Cappellari, María Victoria. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Marzari, Gabriela Lorena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Morales, Gustavo Marcelo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Fungo, Fernando Gabriel. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina

Published
2018
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9. Synthesis of triazole derivatives of levoglucosenone as promising anticancer agents: Effective exploration of the chemical space through retro-za-michael//aza-michael isomerizations

Author

Felipe T. Martins, Ariel M. Sarotti, Rolando A. Spanevello, Javier Girardini, Carolina Di Benedetto, Yi-hsuan Tsai, Carla M. Borini Etichetti, and Alejandra G. Suárez

Subjects
010405 organic chemistry, Chemistry, Organic Chemistry, Ciencias Químicas, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Chemical space, 0104 chemical sciences, biomass-derived, breast cancer, Química Orgánica, Triazole derivatives, triazoles, CIENCIAS NATURALES Y EXACTAS
Abstract

The design and synthesis of biomass-derived triazoles and the in vitro evaluation as potential anticancer agents are described. The discovery of base-catalyzed retro-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues. Fil: Tsai, Yi Hsuan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Borini Etichetti, Carla Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina Fil: Di Benedetto, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina Fil: Girardini Brovelli, Javier Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina Fil: Martins, Felipe Terra. Universidade Federal de Goiás; Brasil Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2018
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10. Electrochemical films deposition and electro-optical properties of bis-carbazol-triphenylamine end-caped dendrimeric polymers

Author

Luis Otero, Maria Ines Mangione, Fernando Fungo, Pablo César Cavallo, Daniela Minudri, and Rolando A. Spanevello

Subjects
chemistry.chemical_classification, OPTOELECTRONIC, Materials science, General Chemical Engineering, Otras Ciencias Químicas, Ciencias Químicas, 02 engineering and technology, Polymer, 010402 general chemistry, 021001 nanoscience & nanotechnology, Triphenylamine, Electrochemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, chemistry, ELECTRODEPOSITION, DENDRIMERIC POLYMERS, 0210 nano-technology, Deposition (chemistry), CIENCIAS NATURALES Y EXACTAS, Nuclear chemistry
Abstract

A family of structurally related π-conjugated star-shape bis-carbazol-triphenylamine end-caped dendrimers was designed, synthetized and characterized as novel organic optoelectronic materials. These compounds hold triphenylamine and carbazole electroactive moieties as dendrimer core and/or periphery groups. Homogeneous and stable electrogenerated polymeric films were obtained from dendrimers over Pt and ITO electrodes. These films showed charge conductivities, reversible electrochemical behavior and electrochromic effect. The hole mobility of the electrodeposited films was found to be dependent of the dendrimeric structure and film morphologies, indicating that the shape and size of the studied dendrimers have a strong effect on their charge transport properties. These results provide data that will contribute to the systematic study for the design of new dendrimers as starting materials for conductive polymers films with potential applications in optoelectronic devices. Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Minudri, Daniela. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Química. Area Electroquímica; Argentina Fil: Cavallo, Pablo César. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Química. Area Electroquímica; Argentina Fil: Otero, Luis Alberto. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Química. Area Electroquímica; Argentina Fil: Fungo, Fernando Gabriel. Universidad Nacional de Rio Cuarto. Facultad de Cs.exactas Fisicoquímicas y Naturales. Departamento de Química. Area Electroquímica; Argentina

Published
2018

11. Soybean hulls, an alternative source of bioactive compounds: Combining pyrolysis with bioguided fractionation

Author

Alejandra G. Suárez, German Francisco Giri, Ricardo L. E. Furlan, Rolando A. Spanevello, Gastón Viarengo, and Eleonora García Véscovi

Subjects
BIOAUTOGRAPHY, BIOMASS RECYCLING, 010405 organic chemistry, Chemistry, PYROLYSIS, Otras Ciencias Químicas, AGRO-INDUSTRIAL RESIDUES, Ciencias Químicas, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Bioguided fractionation, SOYBEAN HULLS, Botany, Organic chemistry, LEVOGLUCOSENONE, Soybean hulls, Agronomy and Crop Science, Pyrolysis, CIENCIAS NATURALES Y EXACTAS
Abstract

The trend for material and energy recovery from residues along with the need to reduce greenhouse gases has led to an increased interest in the thermal exploitation of biomass and/or their wastes. Due to the enormous quantity generated every year, agro-industrial byproducts have an attractive potential to be recycled. One way to do this is by means of pyrolysis, a thermal decomposition of high molecular weight polymers into simpler compounds. In this study, we applied an autographic assay to analyze the biological effect of bio-oils produced by pyrolysis of soybean hulls. The discovery of a compound with antimicrobial activity validated this novel approach as a tool for the generation of bioactive compounds. Fil: Giri, German Francisco. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Viarengo, Gastón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina Fil: Furlan, Ricardo Luis Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Investigaciones para el Descubrimiento de Fármacos de Rosario. Universidad Nacional de Rosario. Instituto de Investigaciones para el Descubrimiento de Fármacos de Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Garcia Vescovi, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2017

12. Mechanistic insight into the acid-catalyzed isomerization of biomass-derived polysubstituted pyrrolidines: an experimental and DFT study

Author

Ariel M. Sarotti, Alejandra G. Suárez, Gabriela Guillermina Gerosa, Rolando A. Spanevello, and Nicolas Grimblat

Subjects
biomass, 010405 organic chemistry, Chemistry, Otras Ciencias Químicas, Organic Chemistry, Ciencias Químicas, Azomethine ylide, Iminium, pyrrolidines, Mechanistic, 010402 general chemistry, 01 natural sciences, Biochemistry, isomerization, Cycloaddition, 0104 chemical sciences, Computational chemistry, Mechanism (philosophy), Acid catalyzed, Organic chemistry, Physical and Theoretical Chemistry, Isomerization, CIENCIAS NATURALES Y EXACTAS
Abstract

The 1,3-dipolar cycloaddition reactions of azomethine ylides is one of the preferred methods for the synthesis of polysubstituted pyrrolidines. The use of chiral dipolarophiles derived from carbohydrates yields enantiomerically pure pyrrolidines, usually in good to excellent endo selectivities, along with other minor stereoisomers. Recently, we found an unusual isomerization event that allowed the isolation of useful pyrrolidines with relative stereochemistries difficult to obtain otherwise. Although a simple and efficient protocol to promote these transformations was developed, the mechanism was not fully unravelled. Herein, after a combination of experimental, spectroscopic and computational studies (using DFT methods) we propose that this isomerization event takes place through a retro-Mannich//Mannich cascade, via the formation of an iminium ion with E geometry. Fil: Gerosa, Gabriela Guillermina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2016

13. Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines

Author

Mauro Danielli, German Francisco Giri, Raúl A. Marinelli, and Rolando A. Spanevello

Subjects
Cell Survival, Clinical Biochemistry, Pharmaceutical Science, Antineoplastic Agents, Related derivatives, 010402 general chemistry, 01 natural sciences, Biochemistry, CYTOTOXIC ACTIVITY, Cell Line, Tumor, Drug Discovery, medicine, Ic50 values, Cytotoxic T cell, Humans, LEVOGLUCOSENONE, Molecular Biology, Cell survival, Cisplatin, 010405 organic chemistry, Chemistry, Otras Ciencias Químicas, Organic Chemistry, Liver Neoplasms, Ciencias Químicas, Bridged Bicyclo Compounds, Heterocyclic, Combinatorial chemistry, 0104 chemical sciences, MICHAEL ADDITION, Glucose, CANCER CELL LINES, Cell culture, Chemotherapy Drugs, Molecular Medicine, Cancer cell lines, HEPATOCARCINOMA, CIENCIAS NATURALES Y EXACTAS, medicine.drug
Abstract

Levoglucosenone has been used as template for the synthesis of a wide variety of compounds with an impressive structural variability. However, scarce work has been done regarding the generation of new bioactive entities. Here we report the cytotoxic effect of levoglucosenone and some related derivatives against hepatocarcinoma cell lines. Compounds were obtained in only one synthetic step and one of them showed an activity within the range of IC50values of cisplatin, a frequently administered chemotherapy drug. Fil: Giri, German Francisco. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Danielli, Mauro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; Argentina Fil: Marinelli, Raul Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2016

14. Experimental and theoretical insights in the alkene-arene intramolecular π-stacking interaction

Author

Carmen Ramírez de Arellano, Rolando A. Spanevello, Ariel M. Sarotti, Valeria Corne, and Alejandra G. Suárez

Subjects
Electron density, Stereochemistry, asymmetric synthesis, Stacking, Biomass, 010402 general chemistry, 01 natural sciences, Full Research Paper, BIOMASS, purl.org/becyt/ford/1 [https], lcsh:QD241-441, lcsh:Organic chemistry, ASYMMETRIC SYNTHESIS, Computational chemistry, CONFORMATIONAL EQUILIBRIUM, Π-STACKING INTERACTION, purl.org/becyt/ford/1.4 [https], conformational equilibrium, ACRYLIC ESTERS, lcsh:Science, chemistry.chemical_classification, Quantum chemical, biomass, 010405 organic chemistry, Alkene, acrylic esters, Otras Ciencias Químicas, Organic Chemistry, Enantioselective synthesis, Ciencias Químicas, π-stacking interaction, 0104 chemical sciences, Chemistry, chemistry, Intramolecular force, lcsh:Q, CIENCIAS NATURALES Y EXACTAS
Abstract

Chiral acrylic esters derived from biomass were developed as models to have a better insight in the aryl-vinyl π-stacking interactions. Quantum chemical calculations, NMR studies and experimental evidences demonstrated the presence of equilibriums of at least four different conformations: π-stacked and face-to-edge, each of them in an s-cis/s-trans conformation. The results show that the stabilization produced by the π-π interaction makes the π-stacked conformation predominant in solution and this stabilization is slightly affected by the electron density of the aromatic counterpart. Fil: Corne, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: De Arellano, Carmen Ramirez. Universidad de Valencia; España Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2016

15. Electropolimerization of Functionalizaed Carbazole End-Capped Dendrimers. Formation of Conductive Films

Author

Luis Otero, Fernando Fungo, Rolando A. Spanevello, Maria Ines Mangione, Luciana Fernandez, Daniel Alejandro Heredia, and Daniela Minudri

Subjects
OPTOELECTRONIC, Materials science, General Chemical Engineering, 02 engineering and technology, 010402 general chemistry, Electrochemistry, Triphenylamine, 01 natural sciences, chemistry.chemical_compound, Dendrimer, Polymer chemistry, DENDRIMERIC POLYMERS, chemistry.chemical_classification, Carbazole, Otras Ciencias Químicas, Ciencias Químicas, Polymer, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Monomer, chemistry, Electrochromism, ELECTRODEPOSITION, 0210 nano-technology, CIENCIAS NATURALES Y EXACTAS, Macromolecule
Abstract

A series of peripherally carbazole functionalized dendrimeric starburst monomers were synthesized and characterized. The electrochemical polymerization over Pt and indium tin oxide electrodes of fully π-conjugated dendrimers allows the generation of electro-active polymeric films. Dendrimers were design with and without electroactive central core (triphenylamine) connected to peripherals moieties, which influence the physicochemical characteristics of the electrogenerated polymers. The versatile electropolymerization methodology allows the generation of thin films of hyperbranched macromolecules with good electrical conductivity, reversible electrochemical processes and electrochromic properties. Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Minudri, Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina Fil: Heredia, Daniel Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina Fil: Fernandez, Luciana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina Fil: Otero, Luis Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina Fil: Fungo, Fernando Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina

Published
2016

16. Synthesis of a 3-Thiomannoside

Author

Ariel M. Sarotti, Rolando A. Spanevello, Alejandra G. Suárez, Maria Ines Mangione, María Betina Comba, and Enrique David Victor Giordano

Subjects
Magnetic Resonance Spectroscopy, XANTATE-THIOCARBONATE, 010402 general chemistry, 01 natural sciences, Biochemistry, 3-THIOMANNOSIDE, purl.org/becyt/ford/1 [https], chemistry.chemical_compound, purl.org/becyt/ford/1.4 [https], Organic chemistry, Molecule, LEVOGLUCOSENONE, Physical and Theoretical Chemistry, Molecular Structure, 010405 organic chemistry, Otras Ciencias Químicas, Organic Chemistry, Ciencias Químicas, Nuclear magnetic resonance spectroscopy, Combinatorial chemistry, 0104 chemical sciences, ENANTIOSPECIFIC SYNTHESIS, chemistry, Yield (chemistry), Mannose, CIENCIAS NATURALES Y EXACTAS, Derivative (chemistry)
Abstract

An efficient and straightforward synthesis of a novel 3-thiomannoside derivative (1,2,4,6-tetra-O-acetyl-3-S-acetyl-3-thio-β-d-mannopyranoside) was developed starting from levoglucosenone. A xanthate-thiocarbonate exchange under acidic conditions was the key step for the new C-S bond. The product was obtained enantiospecifically in very good overall yield. Fil: Comba, María Betina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Giordano, Enrique David Victor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2016
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17. Development of polymer-supported chiral aminoalcohols derived from biomass and their application to asymmetric alkylation

Author

Rolando A. Spanevello, Alejandra G. Suárez, María Celeste Botta, Hernan Biava, and Ernesto G. Mata

Subjects
inorganic chemicals, Solid-phase synthesis, Levoglucosenone, Biomass, Alkylation, 010402 general chemistry, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Drug Discovery, Organic chemistry, 010405 organic chemistry, Chemistry, Otras Ciencias Químicas, organic chemicals, Organic Chemistry, Chiral ligand, Ciencias Químicas, Asymmetric Induction, Diethylzinc, Chiral Ligands, Asymmetric induction, 0104 chemical sciences, 1,2-Aminoalcohols, CIENCIAS NATURALES Y EXACTAS, Polymer supported
Abstract

A synthetic strategy has been developed for the preparation of immobilized 1,2-aminoalcohols starting from easily available and renewable chiral building blocks. They were tested as chiral ligands for the asymmetric diethylzinc addition to carbonyl compounds. Enantioselectivities were comparable to those observed for non-immobilized analogs. These results provide strong evidence for the flexibility of our approach to generate highly valuable supported chiral ligands derived from cellulose-rich materials. Fil: Botta, María Celeste. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Biava, Hernan Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Mata, Ernesto Gabino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

Published
2016

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