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.
From Xu and Wang (Nankai Univ.): C3‐Cyanation of Pyridines: Constraints on Electrophiles and Determinants of Regioselectivity https://onlinelibrary.wiley.com/doi/10.1002/anie.202216894#.Y9ZMC04Xi6I.twitter
From Lukas Gooßen @ruhrunibochum: C−H Fluoromethoxylation of Arenes by Photoredox Catalysis https://onlinelibrary.wiley.com/doi/10.1002/anie.202215920#.Y9I7hoYC62k.twitter
From Altmann @ETH_en : Synthesis and Biological Evaluation of C(13)/C(13′)‐Bis(desmethyl)disorazole Z https://onlinelibrary.wiley.com/doi/10.1002/anie.202212190#.Y9I6PYNWHQI.twitter
Last chance to apply to the post-doctoral position available in my group in Mulhouse (FR). Fluorine chem, Organic chem and homogeneous catalysis. Do not miss the opportunity to join the group! Deadline February 8th.
https://emploi.cnrs.fr/Offres/CDD/UMR7042-VINBIZ-003/Default.aspx
Many thanks to @INC_CNRS for this grant and to @LIMA_UMR7042, @UHA68,@unistra for great support. You still have the chance to apply to join the group for an 18-months post doctoral position. We need you! 🧑🔬👍🏆🏅😉 https://emploi.cnrs.fr/Offres/CDD/UMR7042-VINBIZ-003/Default.aspx
Here is the official offer for the post-doctoral position. Sorry for those who already applied but you need to register and apply via this platform, otherwise I cannot consider your application. A PhD in organic synthesis is required! Thanks for sharing.
#chimie ⚗️ #ResultatScientifique 📕 🔎 l Nouvelle stratégie de synthèse de dérivés fluorés pour la #santé et l’ #agrochimie
Ou comment stabiliser les intermédiaires réactionnels pour arriver au produit souhaité ?
🤝 @CNRS_Alsace @unistra
➡️ https://buff.ly/3GZOwXN
Congratulations to our colleague @DelordWencel for this honorific title of « membre distingué » from @reseauSCF.
The work on the functionalization of difluoro ketones recently published in @angew_chem by the @Leroux_group is highlighted by @INC_CNRS https://www.inc.cnrs.fr/fr/cnrsinfo/nouvelle-strategie-de-synthese-de-derives-fluores-pour-la-sante-et-lagrochimie