Bruno Botta, P. IACOMACCI, Cristina Di Giovanni, Giuliano Delle Monache, Eszter Gács‐Baitz, Maurizio Botta, Andrea Tafi, Federico Corelli, Domenico Misiti,
... Giuliano Delle Monache, Eszter Gacs-Baitz, Maurizio Botta, Andrea Tafi, Federico Corelli, and Domenico MisitiCite this: J. Org. ...
Tópico(s): Enzyme Catalysis and Immobilization
1992 - American Chemical Society | The Journal of Organic Chemistry
Silvio Massa, Marino Artico, Antonello Mai, F Corelli, Mauro Botta, Andrea Tafi, Pantaleoni Gc, Raffaele De Giorgi, MF Coppolino, Alfredo Cagnotto,
... Marino Artico, Antonello Mai, Federico Corelli, Maurizio Botta, Andrea Tafi, Gian Carlo Pantaleoni, Raffaele Giorgi, Maria Francesca Coppolino, ...
Tópico(s): Neuroscience and Neuropharmacology Research
1992 - American Chemical Society | Journal of Medicinal Chemistry
Bruno Botta, M. C. DI GIOVANNI, Giuliano Delle Monache, Maria Cristina De Rosa, Eszter Gács‐Baitz, Maurizio Botta, Federico Corelli, Andrea Tafi, Antonello Santini,
... Rosa, Eszter Gacs-Baitz, Maurizio Botta, Federico Corelli, Andrea Tafi, Antonello Santini, and Cite this: J. Org. Chem. ...
Tópico(s): Inorganic and Organometallic Chemistry
1994 - American Chemical Society | The Journal of Organic Chemistry
Giuseppe Campiani, Antonio Garofalo, Isabella Fiorini, Maurizio Botta, V. NACCI, Andrea Tafi, Alberto Chiarini, Roberta Budriesi, G Bruni, M. R. ROMEO,
... Antonio Garofalo, Isabella Fiorini, Maurizio Botta, Vito Nacci, Andrea Tafi, Alberto Chiarini, Roberta Budriesi, Giancarlo Bruni, and Maria ...
Tópico(s): Phenothiazines and Benzothiazines Synthesis and Activities
1995 - American Chemical Society | Journal of Medicinal Chemistry
Andrea Tafi, Roberta Costi, Maurizio Botta, Roberto Di Santo, Federico Corelli, Silvio Massa, Andrea Ciacci, Fabrizio Manetti, Marino Artico,
The synthesis, anti-Candida activity, and quantitative structure−activity relationship (QSAR) studies of a series of 2,4-dichlorobenzylimidazole derivatives having a phenylpyrrole moiety (related to the antibiotic pyrrolnitrin) in the α-position are reported. A number of substituents on the phenyl ring, ranging from hydrophobic (tert-butyl, phenyl, or 1-pyrrolyl moiety) to basic (NH2), polar (CF3, CN, SCH3, NO2), or hydrogen bond donors and acceptor (OH) groups, were chosen to better understand the interaction ...
Tópico(s): Synthesis and Reactions of Organic Compounds
2002 - American Chemical Society | Journal of Medicinal Chemistry
Serena Pasquini, Claudia Mugnaini, Alessia Ligresti, Andrea Tafi, Simone Brogi, Chiara Falciani, Valentina Pedani, Nicolò Pesco, Francesca Guida, Livio Luongo, Katia Varani, Pier Andrea Borea, Sabatino Maione, Vincenzo Di Marzo, Federico Corelli,
In our search for new cannabinoid receptor modulators, we describe herein the design and synthesis of three sets of indole-based ligands characterized by an acetamide, oxalylamide, or carboxamide chain, respectively. Most of the compounds showed affinity for CB2 receptors in the nanomolar range, with K(i) values spanning 3 orders of magnitude (377-0.37 nM), and moderate to good selectivity over CB1 receptors. Their in vitro functional activity as inverse agonists was confirmed in vivo in the formalin ...
Tópico(s): Neurotransmitter Receptor Influence on Behavior
2012 - American Chemical Society | Journal of Medicinal Chemistry
Andrea Tafi, Cesare Bernardini, Maurizio Botta, Federico Corelli, Matteo Andreini, Adriano Martinelli, Gabriella Ortore, Pier Giovanni Baraldi, Francesca Fruttarolo, Pier Andrea Borea, Tiziano Tuccinardi,
To design and synthesize new potent and selective antagonists of the human A(3) adenosine receptor, pharmacophoric hypotheses were generated with the software Catalyst for a comprehensive set of compounds retrieved from previous literature. Three of these pharmacophores were used to drive the optimization of a molecular model of the receptor built by homology modeling. The alignment of the ligands proposed by Catalyst was then used to manually dock a set of known A(3) antagonists into the binding ...
Tópico(s): Receptor Mechanisms and Signaling
2006 - American Chemical Society | Journal of Medicinal Chemistry
Fabiana Caporuscio, Andrea Tafi, Emmanuel González, Fabrizio Manetti, José A. Esté, Maurizio Botta,
A dynamic target-based pharmacophoric model mapping the CD4 binding site on HIV-1 gp120 was built and used to identify new hits able to inhibit gp120-CD4 protein-protein interactions. Two compounds showed micromolar inhibition of HIV-1 replication in cells attributable to an interference with the entry step of infection, by direct interaction with gp120. Inactivity of compounds toward a M475I strain suggested specific contacts with the Phe43 cavity of gp120.
Tópico(s): Protein Structure and Dynamics
2009 - Elsevier BV | Bioorganic & Medicinal Chemistry Letters
Simone Brogi, Maria Kladi, Constantinos Vagias, Panagiota Papazafiri, Vassilios Roussis, Andrea Tafi,
A ligand-based pharmacophore approach for the prediction of antiestrogenic activity to be used as an in silico screening tool for bioactive compounds including natural products was developed using Catalyst HypoGen. The generated pharmacophore hypothesis (HYPO-7) consisted of five features, namely, one hydrophobic (HY1), two hydrophobic aromatic (HY2), one hydrogen-bond acceptor (HBA), and one hydrogen-bond donor (HBD). HYPO-7 successfully predicted the lack of cytotoxicity of a number of new metabolites ...
Tópico(s): Seaweed-derived Bioactive Compounds
2009 - American Chemical Society | Journal of Chemical Information and Modeling
Jean‐Denis Docquier, V. Calderone, Filomena De Luca, Manuela Benvenuti, Francesco Giuliani, Luca Bellucci, Andrea Tafi, Patrice Nordmann, Maurizio Botta, Gian María Rossolini, Stefano Mangani,
Carbapenem-hydrolyzing class D beta-lactamases (CHDLs) are enzymes found in important Gram-negative pathogens (mainly Acinetobacter baumannii and Enterobacteriaceae) that confer resistance to beta-lactam antibiotics, and notably carbapenems. The crystal structure of the OXA-48 carbapenemase was determined at pH 7.5 and at a resolution of 1.9 A. Surprisingly, and by contrast with OXA-24, the only other CHDL of known crystal structure, the structure of OXA-48 was similar to OXA-10, an enzyme devoid ...
Tópico(s): Bacterial Genetics and Biotechnology
2009 - Elsevier BV | Chemistry & Biology
Marco Radi, Giovanni Maga, Maddalena Alongi, Lucilla Angeli, Alberta Samuele, Samantha Zanoli, Luca Bellucci, Andrea Tafi, Gianni Casaluce, Gianluca Giorgi, Mercedes Armand‐Ugón, Emmanuel González, José A. Esté, Mireille Baltzinger, Guillaume Bec, Philippe Dumas, Eric Ennifar, Maurizio Botta,
The role played by stereochemistry in the C2-substituent (left part) on the S-DABO scaffold for anti-HIV-1 activity has been investigated for the first time. A series of S-DABO analogues, where the double bond in the C2-substituent is replaced by an enantiopure isosteric cyclopropyl moiety, has been synthesized, leading to the identification of a potent lead compound endowed with picomolar activity against RT (wt) and nanomolar activity against selected drug-resistant mutants. Molecular modeling calculation, ...
Tópico(s): Biochemical and Molecular Research
2009 - American Chemical Society | Journal of Medicinal Chemistry
Evita Balducci, Luca Bellucci, Elena Petricci, Maurizio Taddei, Andrea Tafi,
The intramolecular version of the Huisgen cycloaddition is a potentially useful reaction for the stereocontrolled preparation of 1,5-disubstituted and 1,4,5-trisubstiututed triazoles. When α-azido propargyl esters derived from α-amino acids are submitted to [3 + 2] cycloaddition, the expected 4H-[1,2,3]triazolo[5,1-c][1,4]oxazin-6-ones are not formed; rather, an oligomeric cyclic polyester is obtained via a prevailing intermolecular cycloaddition. We have discovered that propargyl α-azido amides undergo ...
Tópico(s): Synthesis and Catalytic Reactions
2009 - American Chemical Society | The Journal of Organic Chemistry
Maria Kladi, Constantinos Vagias, Panagiota Papazafiri, Simone Brogi, Andrea Tafi, Vassilios Roussis,
Five new C15 acetogenin en-ynes (1−5) with a rare tetrahydrofuran moiety and a linear biosynthetic precursor (6) were isolated from an organic extract of Laurencia glandulifera, collected from the island of Crete in the south Aegean Sea. The structures of the new natural products, as well as their relative configuration, were established by means of spectroscopic data analysis. The cytotoxicity of the isolated natural products was evaluated against five human tumor cell lines.
Tópico(s): Plant-derived Lignans Synthesis and Bioactivity
2009 - American Chemical Society | Journal of Natural Products
Fedele Manna, Franco Chimenti, Adriana Bolasco, Daniela Secci, Bruna Bizzarri, Olivia Befani, Paola Turini, Bruno Mondovı̀, Stefano Alcaro, Andrea Tafi,
A novel series of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives have been synthesised and investigated for the ability to inhibit selectively monoamine oxidases, swine kidney oxidase, and bovine serum amine oxidase. The newly synthesised compounds 1-6 proved to be reversible and non-competitive inhibitors of all types of the assayed amine oxidases. Compounds inhibit monoamine oxidases potently, displaying low I(50) values of particular interest. In particular 1-acetyl-3-(2,4-dihydroxyphenyl)- ...
Tópico(s): Chemical Reactions and Mechanisms
2002 - Elsevier BV | Bioorganic & Medicinal Chemistry Letters
Francesco Bondavalli, Maurizio Botta, Olga Bruno, Andrea Ciacci, Federico Corelli, Paola Fossa, Antonio Lucacchini, Fabrizio Manetti, Claudia Martini, Giulia Menozzi, Luisa Mosti, Angelo Ranise, Silvia Schenone, Andrea Tafi, Maria Letizia Trincavelli,
We present a combined computational study aimed at identifying the three-dimensional structural properties required for different classes of compounds to show antagonistic activity toward the A1 adenosine receptor (AR). Particularly, an approach combining pharmacophore mapping, molecular alignment, and pseudoreceptor generation was applied to derive a hypothesis of the interaction pathway between a set of A1 AR antagonists taken from the literature and a model of the putative A1 receptor. The pharmacophore ...
Tópico(s): Pharmacological Receptor Mechanisms and Effects
2002 - American Chemical Society | Journal of Medicinal Chemistry
Bruno Botta, Giuliano Delle Monache, Giovanni Zappia, Domenico Misiti, Maria Camilla Baratto, Rebecca Pogni, Eszter Gács‐Baitz, Maurizio Botta, Federico Corelli, Fabrizio Manetti, Andrea Tafi,
Following our studies on resorcin[4]arenes, we synthesized new macrocycles containing cyanomethyl and aminomethyl side chains. Three stereoisomers (2a-c) of the former were obtained by BF3*Et2O tetramerization of the corresponding trans-cinnamic acid derivative and were shown to be in the 1,2-alternate, cone, and 1,3-alternate conformations. Conversely, the tetraamino derivative 6a in the cone conformation was prepared from the corresponding tetrabromide 3a. The interactions with Cu(II) cations of ...
Tópico(s): Mass Spectrometry Techniques and Applications
2002 - American Chemical Society | The Journal of Organic Chemistry
Bruno Botta, Maurizio Botta, Antonello Filippi, Andrea Tafi, Giuliano Delle Monache, Maurizio Speranza,
Gas-phase proton-bound complexes between a chiral resorcin[4]arene and some representative amino acids, that is, l- and d-alanine or l- and d-serine, were generated in the source of a Fourier transform ion cyclotron resonance mass spectrometer. Gas-phase exchange of the amino acid from the diastereomeric complexes with the enantiomers of 2-butylamine exhibits a significant enantioselectivity, which depends not only upon the configuration of the leaving guest but also on that of the incoming amine. ...
Tópico(s): Molecular Sensors and Ion Detection
2002 - American Chemical Society | Journal of the American Chemical Society
Laura Betti, Maurizio Botta, Federico Corelli, Monia Floridi, Gino Giannaccini, Laura Maccari, Fabrizio Manetti, Giovannella Strappaghetti, Andrea Tafi, Stefano Corsano,
As a part of a program aimed at discovering compounds endowed with α1-adrenoceptor (AR) blocking properties, in this paper we describe the synthesis and biological characterization of the compounds designed to fully match a three-dimensional pharmacophore model for α1-AR antagonists previously developed by our research group. Accordingly, the structure of trazodone (1), identified during a database search performed by using the model as a 3D query, was chosen as the starting point for this study and ...
Tópico(s): Neuroscience and Neuropharmacology Research
2002 - American Chemical Society | Journal of Medicinal Chemistry
Maurizio Botta, Federico Corelli, Fabrizio Manetti, Andrea Tafi,
In the present review we summarize recent work, aimed at a better understanding of the interactions in macromolecule ligand complexes, performed by means of computational tools such as pseudoreceptor generation, molecular docking, conformational search and energy minimization. While the first approach has been applied when the three-dimensional structural properties of the biological target were unknown, the remaining protocols exploited the knowledge of the overall structure of the involved macromolecules ...
Tópico(s): Protein Structure and Dynamics
2002 - Elsevier BV | Il Farmaco
Alberto Vitali, Bruno Giardina, Giuliano Delle Monache, Filippo Della Rocca, Andrea Silvestrini, Andrea Tafi, Bruno Botta,
A new prenyltransferase (PT) enzyme derived from the microsomal fractions of cell cultures of Morus nigra was shown to be able to prenylate exclusively chalcones with a 2′,4′‐dihydroxy substitution and the isoflavone genistein. Computational studies were performed to shed some light on the relationship between the structure of the substrate and the enzymatic activity. PT requires divalent cations, particularly Mg 2+ , to be effective. The apparent K m values for γ,γ‐dimethylallyldiphosphate and 2′, ...
Tópico(s): Plant Gene Expression Analysis
2003 - Wiley | FEBS Letters
Laura Betti, Monia Floridi, Gino Giannaccini, Fabrizio Manetti, Giovannella Strappaghetti, Andrea Tafi, Maurizio Botta,
Tópico(s): Receptor Mechanisms and Signaling
2003 - Elsevier BV | Bioorganic & Medicinal Chemistry Letters
Mariangela Biava, Giulio Cesare Porretta, Delia Deidda, Raffaello Pompei, Andrea Tafi, Fabrizio Manetti,
Tópico(s): Carbohydrate Chemistry and Synthesis
2003 - Elsevier BV | Bioorganic & Medicinal Chemistry
Giuseppe La Regina, Felicia Diodata D’Auria, Andrea Tafi, Francesco Piscitelli, Stefania Olla, Fabiana Caporuscio, Lucia Nencioni, Roberto Cirilli, Francesco La Torre, Nadja Rodrigues de Melo, Steven L. Kelly, David C. Lamb, Marino Artico, Maurizio Botta, Anna Teresa Palamara, Romano Silvestri,
New 1-[(3-aryloxy-3-aryl)propyl]-1 H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives ( 10, 12, 14, 18- 20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant ...
Tópico(s): Herbal Medicine Research Studies
2008 - American Chemical Society | Journal of Medicinal Chemistry
Simone Brogi, Federico Corelli, Vincenzo Di Marzo, Alessia Ligresti, Claudia Mugnaini, Serena Pasquini, Andrea Tafi,
This paper describes a three-dimensional quantitative structure–selectivity relationships (3D-QSSR) study for selectivity of a series of ligands for cannabinoid CB1 and CB2 receptors. 3D-QSSR exploration was expected to provide design information for drugs with high selectivity toward the CB2 receptor. The proposed 3D computational model was performed by Phase and generated taking into account a number of structurally diverse compounds characterized by a wide range of selectivity index values. The ...
Tópico(s): Neurotransmitter Receptor Influence on Behavior
2010 - Elsevier BV | European Journal of Medicinal Chemistry
Cleofe Palocci, Mariangela Falconi, Stefano Alcaro, Andrea Tafi, Roberta Puglisi, Francesco Ortuso, Maurizio Botta, Lilia Alberghina, E. Cernia,
Candida rugosa lipase crude preparations (CRL) catalyse the regioselective acylation of methyl 6-O-trytil beta-d-glucopyranoside in organic solvents, using vinyl acetate as acyl donor. The ratio of the two products formed, namely methyl 2-O acetyl 6-O-trytil beta-d-glucopyranoside and methyl 3-O acetyl 6-O-trytil beta-d-glucopyranoside was found to be markedly affected by the nature of the reaction medium. In hydrophobic solvents values up to 80% of the monoacetylated product in position C-3 were ...
Tópico(s): Carbohydrate Chemistry and Synthesis
2007 - Elsevier BV | Journal of Biotechnology
Claudia Mugnaini, Maddalena Alongi, Andrea Togninelli, Harsukh Gevariya, Antonella Brizzi, Fabrizio Manetti, Cesare Bernardini, Lucilla Angeli, Andrea Tafi, Luca Bellucci, Federico Corelli, Silvio Massa, Giovanni Maga, Alberta Samuele, Marcella Facchini, Imma Clotet‐Codina, Mercedes Armand‐Ugón, José A. Esté, Maurizio Botta,
A series of novel S-DABO analogues, characterized by different substitution patterns at positions 2, 5, and 6 of the heterocyclic ring, were synthesized in a straightforward fashion by means of parallel synthesis and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Most of the compounds proved to be highly active on the wild-type enzyme both in enzymatic and cellular assays, with one of them emerging as the most active reverse transcriptase inhibitor reported so far (EC50wt = ...
Tópico(s): Click Chemistry and Applications
2007 - American Chemical Society | Journal of Medicinal Chemistry
Bruno Botta, Ilaria D’Acquarica, Laura Nevola, Fabiola Sacco, Zara Valbuena Lopez, Giovanni Zappia, Caterina Fraschetti, Maurizio Speranza, Andrea Tafi, Fabiana Caporuscio, Matthias C. Letzel, Jochen Mattay,
Abstract On the research avenue opened by the rigidified double‐spanned resorcin[4]arene 1 , we have synthesized both enantiomers of the two chiral basket resorcin[4]arenes 3 and 4 , each containing two 1,2‐diaminocyclohexane and 1,2‐diphenylethylenediamine bridges, respectively. In the new compounds, the aromatic rims assume the expected flattened cone arrangement, whereas two different conformations, tentatively designated as “open wings” and “folded wings”, were attributed to the bridge substituents ...
Tópico(s): Molecular Sensors and Ion Detection
2007 - Wiley | European Journal of Organic Chemistry
Fabiana Caporuscio, Andrea Tafi,
A pharmacophore represents a simple and intuitive concept that can be used in many different drug discovery applications. Ligand-based and structure-based pharmacophore models continue to play a pivotal role in hit discovery and may guide lead optimization. Moreover, owing to the versatility of the pharmacophore concept, pharmacophore modelling has been routinely used in combination with other molecular modelling techniques. The synergistic use of different tools in drug discovery workflows may ...
Tópico(s): Analytical Methods in Pharmaceuticals
2011 - Bentham Science Publishers | Current Medicinal Chemistry
Paola Castelli, Angelo Casu, Paola Casti, Carla Lobina, Mauro A.M. Carai, Giancarlo Colombo, Maurizio Solinas, Daniela Giunta, Claudia Mugnaini, Serena Pasquini, Andrea Tafi, Simone Brogi, Gian Luigi Gessa, Federico Corelli,
The potential efficacy of GABA(B) receptor agonists in the treatment of pain, drug addiction, epilepsy, cognitive dysfunctions, and anxiety disorders is supported by extensive preclinical and clinical evidence. However, the numerous side effects produced by the GABA(B) receptor agonist baclofen considerably limit the therapeutic use of this compound. The identification of positive allosteric modulators (PAMs) of the GABA(B) receptor may constitute a novel approach in the pharmacological manipulation ...
Tópico(s): Receptor Mechanisms and Signaling
2011 - American Society for Pharmacology and Experimental Therapeutics | Journal of Pharmacology and Experimental Therapeutics
Ilaria D’Acquarica, Antonella Cerreto, Giuliano Delle Monache, Fabiana Subrizi, Alberto Boffi, Andrea Tafi, Stefano Forli, Bruno Botta,
This paper deals with the design, synthesis, and evaluation of a new series of receptors for protein surface recognition. The design of these agents is based around the attachment of four constrained dipeptide chains onto a central resorc[4]arene scaffold. By varying the sequence, nature, and stereochemistry of the chains we prepared anionically functionalized N-linked peptidoresorc[4]arenes 12, 13, and 17 by Pd/C-catalyzed hydrogenation of the corresponding benzyl esters 10, 11, and 16. From this ...
Tópico(s): Molecular Sensors and Ion Detection
2011 - American Chemical Society | The Journal of Organic Chemistry