التفاصيل البيبلوغرافية
| العنوان: |
Cross-coupling reactions on azetidinone moieties: facile access to novel potential antibacterial ß-lactam agents |
| المؤلفون: |
Faure, Fanny, Rosales-Hurtado, Miyanou, Zambon, Margot, Docquier, Jean-Denis, Licznar-Fajardo, Patricia, Vo-Hoang, Yen, Peyrottes, Suzanne, Gavara, Laurent |
| المساهمون: |
Institut des Biomolécules Max Mousseron Pôle Chimie Balard (IBMM), Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Université de Montpellier (UM), Università degli Studi di Siena = University of Siena (UNISI), PHYSE: Pathogènes Hydriques, Santé, Environnement (PHYSE), Hydrosciences Montpellier (HSM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM), CHU Montpellier = Montpellier University Hospital, Centre Hospitalier Régional Universitaire Montpellier (CHRU Montpellier), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Division Chimie Organique de la Société Chimique d’Italie, Société chimique de France, ANR-19-CE18-0003,ABR-Breaker,Approche innovante pour contrer la résistance bactérienne engendrée par les ß-lactamases(2019), ANR-16-IDEX-0006,MUSE,MUSE(2016) |
| المصدر: |
Vrtual Symposium for Young Organic Chemists - ViSYOChem ; https://hal.science/hal-04833525 ; Vrtual Symposium for Young Organic Chemists - ViSYOChem, Division Chimie Organique de la Société Chimique d’Italie; Société chimique de France, Jun 2024, Webinar, Italy |
| بيانات النشر: |
CCSD |
| سنة النشر: |
2024 |
| المجموعة: |
Université de Montpellier: HAL |
| مصطلحات موضوعية: |
[CHIM]Chemical Sciences |
| جغرافية الموضوع: |
Webinar, Italy |
| الوصف: |
International audience ; Since the introduction of penicillin in 1941, the use of antibiotics significantly decreased the death rate associated with bacterial infections. Today, 60% of prescribed antibacterial drugs belong to the β-lactam family, characterized by a crucial four membered β-lactam ring (e.g., cephalosporin, monobactam). However, their intensive use leads to the emergence of bacterial resistance especially in Gram-negative bacteria through the expression of β-lactamases. Faced with this deadly threat, the WHO draw up a list of priority pathogens and the first priority concerns Gram-negative β-lactamase producers. Nowadays, the main therapeutic class of antibiotics available remains the β-lactam derivatives and their development is a real challenge. Indeed, substituents at C-3, C-4, and C-7 of cephalosporins as well as at N-1 of monobactams are key positions for antimicrobial activity, and their chemical modifications are tricky. The last developments are well illustrated by the chemical structure of the recently marketed cephalosporin: Cefiderocol. Our group is also working in this area for many years with the development of β-lactam analogs. The modification of lateral chains generally requires long synthetic routes, low overall yields and toxic reagents. Here, we propose a simple way to functionalize cephalosporin at C-3 position through an optimized palladium-catalyzed cross-coupling reaction between a vinyl triflate and an aromatic boronic acid. We also exposed a functionalization of monobactam at N-1 using a Buchwald-Hartwig cross-coupling reaction between the nitrogen atom of the β-lactam ring and bromo derivatives. These pallado-catalyzed reactions involved the use of commercially available base, ligands, catalysts and β-lactam intermediates and are therefore a promising pathway to easily access novel β-lactam structures. |
| نوع الوثيقة: |
conference object |
| اللغة: |
English |
| الاتاحة: |
https://hal.science/hal-04833525 |
| رقم الانضمام: |
edsbas.B87DFB2D |
| قاعدة البيانات: |
BASE |