Pyrrolo-imidazo[1,2- a ]pyridine Scaffolds through a Sequential Coupling of N -Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application
| Autor: | Abderrahman El Bouakher, Mouad Alami, Pascal Retailleau, Jérôme Bignon, Kena Zhang, Abdallah Hamze, Hélène Levaique |
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| Přispěvatelé: | Laboratoire de Chimie Physique & de Chimie Bioorganique, URAC 22 (LCPCB), Faculte des sciences et Techniques Mohammedia [Casablanca] (FSTM), Université Hassan II [Casablanca] (UH2MC)-Université Hassan II [Casablanca] (UH2MC), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Biomolécules : Conception, Isolement, Synthèse (BioCIS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Annulation
010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Context (language use) Biological activity 010402 general chemistry 01 natural sciences Small molecule Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Sequential coupling Pyridine Rapid access Nitro [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2019, 84 (21), pp.13807-13823. ⟨10.1021/acs.joc.9b02018⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.9b02018⟩ |
| Popis: | A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(arylvinyl)imidazo[1,2-a]pyridine derivatives. Optimization of Cadogan-reductive conditions allowed the conversion of the obtained nitro derivative to a new scaffold of the type 3-aryl-1H-pyrrolo-imidazo[1,2-a]pyridine. This method provides rapid access to new libraries in the context of diversity-oriented synthesis, which intends to generate small molecules with a large structure diversity in an efficient manner. Screening of the biological activity of the newly generated compounds leads to the identification of a new promising compound 5cc, which exhibits good antiproliferative activity in the submicromolar range against a human colon cancer cell line. |
| Databáze: | OpenAIRE |
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