Coupling Interrupted Fischer and Multicomponent Joullié‐Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics
| العنوان: | Coupling Interrupted Fischer and Multicomponent Joullié‐Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics |
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| المؤلفون: | Maria Grazia Ferraro, Antonella Ilenia Alfano, Angela Zampella, Heiko Lange, Elisabetta Buommino, Carlo Irace, Margherita Brindisi |
| المساهمون: | Alfano, A. I., Buommino, E., Ferraro, M. G., Irace, C., Zampella, A., Lange, H., Brindisi, M., Alfano, A, Buommino, E, Ferraro, M, Irace, C, Zampella, A, Lange, H, Brindisi, M |
| المصدر: | ChemMedChem. 16:3795-3809 |
| بيانات النشر: | Wiley, 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | multicomponent reaction, flow chemistry, Peptidomimetic, Imine, Molecular Conformation, Microbial Sensitivity Tests, Biochemistry, Staphylococcus epidermidi, chemistry.chemical_compound, Anti-Bacterial Agent, Drug Discovery, Staphylococcus epidermidis, General Pharmacology, Toxicology and Pharmaceutics, Pharmacology, sustainable synthesi, Microbial Sensitivity Test, Biofilm, Organic Chemistry, Stereoisomerism, Flow chemistry, Combinatorial chemistry, Anti-Bacterial Agents, chemistry, Coupling (computer programming), Biofilms, Yield (chemistry), Reagent, Chemical diversity, Batch processing, Molecular Medicine, privileged scaffold, Peptidomimetics |
| الوصف: | The generation of peptidomimetic substructures for medicinal chemistry purposes requires effective and divergent synthetic methods. We present in this work an efficient flow process that allows quick modulation of reagents for Joullié-Ugi multicomponent reaction, using spiroindolenines as core motifs. This sterically hindered imine equivalent could successfully be diversified using various isocyanides and amino acids in generally good space-time yields. A telescoped flow process combining interrupted Fischer reaction for spiroindolenine synthesis and subsequent Joullié-Ugi-type modification resulted in product formation in very good overall yield in less than 2 hours compared to 48 hours required in batch mode. The developed protocol can be seen as a general tool for rapid and facile generation of peptidomimetic compounds. We also showcase preliminary biological assessments for the prepared compounds. |
| وصف الملف: | ELETTRONICO |
| تدمد: | 1860-7187 1860-7179 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::811f4b06515d91fdce9be459ad68a320Test https://doi.org/10.1002/cmdc.202100474Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....811f4b06515d91fdce9be459ad68a320 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 18607187 18607179 |
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