2021-01- Synthesis and Physico-Chemical Properties of 2-SF5-(Aza)Indoles, A New Family of SF5-Heterocycles
Structural diversity in heterocyclic chemistry is key to unlock new properties and modes of action. In this regard, heterocycles embedding emerging fluorinated substituents hold great promises. Herein is described a strategy to access 2-SF5-(aza)indoles for the first time. The sequence relies on the radical addition of SF5Cl to the alkynyl π-system of 2-ethynyl anilines followed by a cyclization reaction. A telescoped sequence is proposed making this strategy veryappealing and reproducible on gram scale. Downstream functionalizations are also demonstrated, allowing an easy diversification of N- and C3-positions. Ames test, pKa, logP and DSC measurements of several fluorinated 2-Rf-indoles are also disclosed. These studies highlight the strategic advantages that a C2- pentafluorosulfanylated motif impart to a privileged scaffold such as indole.
2021-02- Molecular Mechanisms Underpinning the Circulation and Cellular Uptake of Mycobacterium ulcerans Toxin Mycolactone
Tello Rubio, B.; Bugault, F.; Baudon, B.; Raynal, B.; Brûlé, S.; Morel, J.-D.; Saint-Auret, S.; Blanchard, N.; Demangel, C.; Guenin-Macé, L. Front. Pharmacol. 2021, 12, 733496.
Mycolactone is a diffusible lipid toxin produced by Mycobacterium ulcerans, the causative agent of Buruli ulcer disease. Altough bacterially derived mycolactone has been shown to traffic from cutaneous foci of infection to the bloodstream, the mechanisms underpinning its access to systemic circulation and import by host cells remain largely unknown. We demonstrate that mycolactone specific association to serum albumin and lipoproteins is necessary for its solubilization and is a major mechanism to regulate its bioavailability. Overall, we suggest a new mechanism of transport and cell entry, challenging the dogma that the toxin enters host cells via passive diffusion.
2021-03- Oxetanes and Oxetenes: Fused-Ring Derivatives
Blanchard, N.; Bizet, V.; Brach, N.; Rummler, L.; Kaliappan, K. P. in Comprehensive Heterocyclic Chemistry IV, Vol. 2 (Eds.: D. S. Black, J. Cossy, C. V. Stevens), Elsevier, Oxford, 2022, pp. 257-286.
Fused and spirooxetanes, oxetenes and β-lactones are important classes of compounds that have found numerous applications in various areas of chemistry including medicinal chemistry and total synthesis of natural products. In this chapter, the main achievements from the theoretical and synthetic point of views since its last edition are discussed.
Very grateful to be selected as member of the Early Career Advisory Board of Tetrahedron and Tetrahedron Letters. Looking forward for exciting new adventures! @ELSchemistry @LIMA_UMR7042 @INC_CNRS @unistra @UHA68 @TetrahedronChem https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
A few spots remain for the best live conference you’ll attend: 18th Meeting of the French American Chemical Society June 12–16, 2022 in sunny #CharlestonSC at the lovely #HotelEmeline! Register: http://facs-symposium.unistra.fr *TODAY*! #DrugDiscovery #NewTechnologies #OrganicChemistry
In “Process Development of a Novel Route to Rilpivirine Hydrochloride” Laurent Petit of #Minakem presents the transformation of initial lab-scale synthetic procedures into a pilot-scale process. #Rilpivirine #HIVTreatment #FACSXVIII
Very grateful to be selected as member of the Early Career Advisory Board of Tetrahedron and Tetrahedron Letters. Looking forward for exciting new adventures! @ELSchemistry @LIMA_UMR7042 @INC_CNRS @unistra @UHA68 @TetrahedronChem https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
Please check our latest contribution just accepted @angewnandte. We succeeded to design a new reagent able to perform deoxyfluorination of CO2 as well as C-SF5 bond formation.
https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202204623#.Ymf445d8TsE.twitter
Nous allons bénéficier d’un financement de thèse pour octobre 2022 intitulé « Déaromatisation électrochimique d’azahétérocycles par voie radicalaire ». Si vous êtes intéressés vous pouvez trouver plus de détails sur le site du COBRA (https://www.lab-cobra.fr/wp-content/uploads/2022/03/Thèse-Rouen-2022-pour-diffusion.pdf)
Félicitations Xavier, une reconnaissance plus que méritée!!!
Congratulations to our colleague @BizetVincent who has been nominated member of the early advisory board of Tetrahedron Letters @ELSchemistry. @CNRS_Alsace @UHA68 @unistra @INC_CNRS https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
Aujourd'hui le LIMA @CNRS_Alsace recevait des étudiants du lycée Jean Rostand de @acstrasbourg pour une visite des laboratoires et un échange avec des élève ultra motivés. Mention spéciale à leur professeur passionné!