SALOM-ROIG Xavier
Thème de Recherche: Synthèses Stéréosélectives & Acides Aminés Modifiés
xavier.salom-roig
umontpellier.fr
0467144865
Bureau: 0, Bât: 17 - Site : Faculté des sciences
Productions scientifiques :
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Highly Enantioselective Access to alpha-Dibenzylamino Ketones from Chiral Nonracemic alpha-Bromo alpha'-Sulfinyl Ketones by Dynamic Kinetic Resolution: Synthesis of (2R, 1'S)-2-[1-(Dibenzylamino)alkyl]oxiranes 
Auteur(s): Salom-Roig X.
(Article) Publié:
European Journal Of Organic Chemistry, vol. p.1300-1309 (2011)
Ref HAL: hal-00602366_v1
DOI: 10.1002/ejoc.201001403
Résumé: A novel and efficient synthesis of enantiomerically pure alpha-dibenzylamino alpha'-sulfinyl ketones starting from a mixture of both epimers of alpha-bromo alpha'-(R)-sulfinyl Ketone has been realized through combined in situ substitution-epimerization in so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substituted alpha-(S)-dibenzylamino alpha'-(R)-sulfinyl ketones were obtained in good yields with excellent diastereoselectivities. The utility of these derivatives was further illustrated with a highly stereoselective synthesis of syn-(2R, 1'S)-2-(1-dibenzylaminoalkyl)oxiranes.
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Exploration of potential prodrug approach of the bis-thiazolium salts T and T4 for orally delivered antimalarials.
Auteur(s): Caldarelli S., Boisbrun Michel, Alarcon Karine, Hamzé Abdallah, Ouattara Mahama, Salom-Roig X., Maynadier M., Wein Sharon, Peyrottes S., Pellet Alain, Calas M., Vial Henri J
(Article) Publié:
Bioorganic & Medicinal Chemistry Letters / Bioorganic And Medicinal Chemistry Letters, vol. 20 p.3953-3956 (2010)
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Chiral synthetic pseudopeptidic derivatives as triplet excited state quenchers
Auteur(s): Salom-Roig X., Martinez J., Burguete M. Isabel, Galindo Francisco, Luis Santiago V., Miranda Miguel A., Morant-Minana Maria C., Pérez-Prieto Julia
(Article) Publié:
Tetrahedron Letters, vol. 50 p.4859-4862 (2009)
Ref HAL: hal-00602150_v1
DOI: 10.1016/j.tetlet.2009.06.047
Résumé: The behavior of 6 pseudopeptidic models, synthesized by connecting different protected amino acids (Trp, Tyr, Phe, and Lys) with various diamino spacers, as quenchers of the triplet excited state of tiaprofenic acid (and its methyl ester), has been investigated. A series of quenching constants have been determined, which depend on the nature of the quencher and on the stereochemistry of the excited drug. A significant degree of stereodifferentiation has been found for the peptidomimetic synthesized with Phe and Tyr linked by a piperazine bridge. The obtained results support the utility of laser flash photolysis (LFP) as a tool to investigate the interactions between photoexcited drugs and simple models of binding sites in proteins.
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Fluorescence and mass spectrometry studies of the interaction between naproxen and syntetic pseudopeptidic models in organic media
Auteur(s): Salom-Roig X.
(Article) Publié:
Tetrahedron / Tetrahedron [London]; Tetrahedron Suppl; Tetrahedron (London), vol. 65 p.7801-7808 (2009)
Ref HAL: hal-00602123_v1
DOI: 10.1016/j.tet.2009.07.031
Résumé: Time-resolved/steady-state fluorescence and mass spectrometry measurements have shown the preferential binding of a non-steroidal anti-inflammatory drug (NSAID) like naproxen 4 to a synthetic pseudopeptidic receptor built using Phe (9), i.e., bearing an aromatic ring, compared to another model synthesized using Lys (8), i.e., lacking such aromatic ring but with a basic binding site. The quenching of the emission of naproxen by models 8 and 9 has been measured in solvents of different nature and analyzed by means of the Stern-Volmer methodology. In non-polar solvent (dichloromethane) the fluorescence of 4 is quenched to a higher extent by 8 than by 9 but in polar medium (methanol) the opposite occurs. The result in methanol is compatible with the existence of π-π stacking interactions between the aromatic rings of naproxen and the aromatic ring of 9. In order to proof this model, mass spectrometry measurements have confirmed the higher stability of the complex formed by 4 and 9 over the related one formed with 8. The observed phenomenon could help to understand the importance of aromaticity in the interactions between NSAIDs and more complex biological macromolecules like misfolded proteins, involved in the development of Alzheimer's disease and other neuropathologies.
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A Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin-607, Pamamycin-593, and Pamamycin-612D Precursors
Auteur(s): Lanners Steve, Norouzi-Arasi Hassan, Salom-Roig X., Hanquet Gilles
(Article) Publié:
Angewandte Chemie International Edition, vol. 46 p.7086-7089 (2007)
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