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13. Antitumor agents 7. Synthesis, antiproliferative activity and molecular modeling of new l-lysine-conjugated pyridophenoxazinones as potent DNA-binding ligands and topoisomerase IIα inhibitors

Author

Antonio Lavecchia, Anna Cioce, Silvana Pedatella, Michele Manfra, Carmen Cerchia, A. Bolognese, Pedatella, S., Cerchia, C., Manfra, M., Cioce, A., Bolognese, A., and Lavecchia, A.

Subjects
Models, Molecular, Molecular model, Carboxamide, Antiproliferative activity, Ligands, 01 natural sciences, Antineoplastic Agent, chemistry.chemical_compound, Drug Discovery, Topoisomerase II Inhibitors, 0303 health sciences, Molecular Structure, General Medicine, DNA, Neoplasm, Docking studie, Linear Model, Human, Base pair, medicine.drug_class, DNA damage, Stereochemistry, Oxazine, Ligand, Antineoplastic Agents, 03 medical and health sciences, Structure-Activity Relationship, Cell Line, Tumor, Oxazines, medicine, Pyridophenoxazinone, Humans, 030304 developmental biology, Cell Proliferation, Pharmacology, Binding Sites, Dose-Response Relationship, Drug, 010405 organic chemistry, Lysine, Organic Chemistry, Binding Site, 0104 chemical sciences, DNA Topoisomerases, Type II, chemistry, Docking (molecular), Linear Models, Neoplastic cell, Topoisomerase-II Inhibitor, Drug Screening Assays, Antitumor, DNA, Topoisomerase II inhibitor
Abstract

A series of l -lysine-conjugated pyridophenoxazinones 2–5 and 2′-5′ were designed and synthesized for developing compounds with multimodal anticancer potentialities. All compounds inhibited the proliferation of a panel of human liquid and solid neoplastic cell lines. 2 and 5 were the most active compounds with IC50 values in the submicromolar range. UV–vis, 1H NMR, unwinding, and docking experiments demonstrated that they intercalate between the middle 5′-GC-3′ base pairs with the carboxamide side chain lying into major groove. Charge-transfer contribution to the complex stability, evaluated by ab initio calculations, was found to correlate with cytotoxicity. Relaxation and cleavage assays showed that 2 and 5 selectively target Topo IIα over Topo IIβ and stimulate the formation of covalent Topo II–DNA complexes, functioning as poisons. Moreover, compound 5 induced DNA damage and arrested MCF-7 cells at the G2/M phase. Altogether, the work provides interesting structure-activity relationships in the pyridophenoxazinone- l -lysine conjugate series and identifies 5 as a promising candidate for further in vivo evaluation.

Published
2019

14. Asymmetric Synthesis of 1,3-Dithiolane Nucleoside Analogues

Author

Annalisa Guaragna, Romualdo Caputo, Giovanni Palumbo, Silvana Pedatella, Caputo, Romualdo, Guaragna, A., Palumbo, G., Pedatella, S., Guaragna, Annalisa, Palumbo, Giovanni, Pedatella, Silvana, Caputo, R., R., Caputo, A., Guaragna, and G., Palumbo

Subjects
Chemistry, Anti hiv, Stereochemistry, Organic Chemistry, Enantioselective synthesis, General Medicine, Nucleoside analogue, anti-HIV, Ring (chemistry), Dithiolane, chemistry.chemical_compound, Nucleic acid, Sugar moiety, Physical and Theoretical Chemistry, Enantiomer, Chirality (chemistry), dithiolane, Nucleoside
Abstract

We report the ready asymmetric synthesis of nucleoside analogues containing a 1,3-dithiolane ring that mimics the sugar moiety of natural nucleosides. The synthesis is accomplished in three main steps from benzoyloxyethanal 1,3-dithiolane, the key step being its conversion into a chiral monosulfoxide by a modified Sharpless sulfo-oxygenation reaction. The nucleoside analogues were obtained in good overall yields and with excellent enantiomeric excesses. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Published
2003
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15. Mild Stereoselective Synthesis of Fully Protected 1,6-Dioxaspiro[4.5]dec-3-ene Derivatives of Sugars

Author

Romualdo Caputo, Francesco Solla, Annalisa Guaragna, Giovanni Palumbo, Silvana Pedatella, Caputo, R., Guaragna, A., Palumbo, Giovanni, Pedatella, S., Solla, F., R., Caputo, Guaragna, Annalisa, G., Palumbo, Pedatella, Silvana, F., Solla, Caputo, Romualdo, and Palumbo, G.

Subjects
Stereochemistry, Chemistry, Organic Chemistry, Organic chemistry, Stereoselectivity, Physical and Theoretical Chemistry, Ene reaction
Published
2002
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16. A new approach to the synthesis of enantiomerically pure 4-deoxy sugars

Author

Romualdo Caputo, Annalisa Guaragna, Giovanni Palumbo, Silvana Pedatella, Francesco Solla, R., Caputo, A., Guaragna, G., Palumbo, Pedatella, Silvana, F., Solla, Caputo, Romualdo, Guaragna, A., Palumbo, Giovanni, Pedatella, S., Solla, F., Guaragna, Annalisa, Silvana, Pedatella, and Francesco, Solla

Subjects
chemistry.chemical_classification, Primary (chemistry), Double bond, Stereochemistry, hexoses, Organic Chemistry, Allylic alcohol, Biochemistry, Aldehyde, chemistry, Electrophile, monosaccharide, Moiety, Cis–trans isomerism
Abstract

In a recent paper2 we have reported the design and synthesis of 3-C-lithiated 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybenzyl)oxy]methane (1) which can be utilized as an allylic alcohol anion equivalent and leads to three-carbon elongations of various electrophiles by introduction of a fully protected hydroxypropenyl moiety. The latter contains a double bond, which can be unravelled to the cis configuration by diastereoselective removal3 of the dimethylene-disulfur bridge, as well as a protected primary hydroxyl group that, depending on the deprotection conditions used (DDQ/NaBH4 or DDQ), may either lead to the free allylic alcohol or to an α,β-unsaturated aldehyde.

Published
2000

17. A Versatile Synthesis of Enantiomerically Pure D- and L-Pyranosyl Nucleoside Analogues

Author

Romualdo Caputo, Annalisa Guaragna, Silvana Pedatella, Giovanni Palumbo, Caputo, Romualdo, Guaragna, A., Palumbo, G., Pedatella, S., Romualdo, Caputo, Guaragna, Annalisa, Palumbo, Giovanni, Silvana, Pedatella, R., Caputo, A., Guaragna, G., Palumbo, and Pedatella, Silvana

Subjects
Nucleoside analogues, Chemistry, Reagent, Genetics, chemistry.chemical_element, Biochemistry, Combinatorial chemistry, Carbon, Modified nucleosides, Nucleoside
Abstract

2-[[O-(p-Methoxybenzyl)-oxy]methyl]-5,6-dihydro-1,4-dithiin 1 is a versatile three carbon homologation reagent which has been conveniently used in the synthesis of enantiomerically pure modified nucleosides.

Published
1999
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18. A one-step synthesis of 2,3-dihydro-1,4-benzothiazines and phenothiazines from 1,3-thiazolidine derivatives of cyclohexanones

Author

Carla Ferreri, Giovanni Palumbo, Luigi Longobardo, Domenico Mastroianni, Silvana Pedatella, Romualdo Caputo, Caputo, R, Ferreri, C, Longobardo, Luigi, Mastroianni, D, Palumbo, G, Pedatella, S., R., Caputo, C., Ferreri, D., Mastroianni, G., Palumbo, and Pedatella, Silvana

Subjects
Pharmacology, chemistry.chemical_compound, Chloroform, Bicyclic molecule, Chemistry, Organic Chemistry, Thiazolidine, Anhydrous, Organic chemistry, One-Step, Optically active, Analytical Chemistry
Abstract

N-Acetyl-1,3-thiazolidine derivatives of cyclohexanones, when treated with a threefold excess N-bromosuccinimide in anhydrous chloroform at room temperature, smoothly afford N-acetyl-2,3-dihydro-1,4-benzothiazines. This represents the first general route to such heterocyclic system in one step from aliphatic precursors. The synthesis of optically active N-acetyl-2,3-dihydro-1,4-benzothiazines is also reported

19. Stereoselective synthesis of fully protected (S)-1,7-dioxaspiro[5,5]undec-4-ene derivatives of sugars

Author

Pasquale Festa, Silvana Pedatella, Annalisa Guaragna, Romualdo Caputo, Giovanni Palumbo, Umberto Ciriello, Caputo, Romualdo, Ciriello, U., Festa, P., Guaragna, A., Palumbo, G., Pedatella, S., U., Ciriello, Festa, Pasquale, Guaragna, Annalisa, Palumbo, Giovanni, Pedatella, Silvana, and Caputo, R.

Subjects
chemistry.chemical_classification, Carbohydrate, Double bond, Chemistry, Spiro compound, Organic Chemistry, Dithiins, Lactone, Derivative (finance), Reagent, Polymer chemistry, Organic chemistry, Stereoselectivity, Physical and Theoretical Chemistry, Ene reaction
Abstract

Perbenzylated 1,7-dioxaspiro[5,5]undec-4-ene derivatives of sugars are obtained in three steps, starting from fully protected glycono-1,5-lactones. The procedure is based on the attack of a lithiated dithiinyl reagent (6) on the starting δ-glyconolactone. The C-glycosidation leads to the sole thermodynamically more stable α-hemiacetal derivative, the spirocyclization of which is then accomplished with BF3·Et2O. The fully protected unsaturated spiroacetals can be smoothly desulfurized for the purpose of any further elaborations of the free double bond. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

20. A new three carbon homologation via sulfur containing heterocyclic systems

Author

Giovanni Palumbo, Annalisa Guaragna, Silvana Pedatella, Romualdo Caputo, Caputo, Romualdo, Guaragna, A., Palumbo, G., Pedatella, S., Romualdo, Caputo, Guaragna, Annalisa, Palumbo, Giovanni, and Silvana, Pedatella

Subjects
chemistry.chemical_classification, Propenyl, Allylic rearrangement, Double bond, Organic Chemistry, Acrolein, Biochemistry, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Reagent, Electrophile, Organic chemistry, Molecule, Moiety
Abstract

A new reagent, based on a 5,6-dihydro-1,4-dithiin heterocyclic system1, has been devised and conveniently used for 3 carbon elongations of various electrophiles. In fact, it acts as either a propenyl alcohol or an acrolein anion equivalent, introducing into the new molecule a moiety consisting of fully protected double bond and allylic oxygen.

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