Synthesis, in-vitro biological evaluation, and molecular docking study of novel spiro-β-lactam-isatin hybrids
| Autor: | Aliasghar Jarrahpour, Zahra Jowkar, Zahra Haghighijoo, Roghayeh Heiran, Javad Ameri Rad, Véronique Sinou, Florent Rouvier, Christine Latour, Jean Michel Brunel, Namık Özdemir |
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| Přispěvatelé: | Shiraz University (Shiraz University ), University of Louisiana, Membranes et cibles thérapeutiques (MCT), Aix Marseille Université (AMU)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Recherche Biomédicale des Armées (IRBA), Ondokuz Mayis University (OMU), Brunel, Jean Michel, Aix Marseille Université (AMU)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Recherche Biomédicale des Armées [Brétigny-sur-Orge] (IRBA) |
| Rok vydání: | 2022 |
| Předmět: |
[SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry
Molecular Biology/Structural Biology [q-bio.BM] [SDV.BBM.BS] Life Sciences [q-bio]/Biochemistry Molecular Biology/Structural Biology [q-bio.BM] [CHIM.THER] Chemical Sciences/Medicinal Chemistry Organic Chemistry 2-azetidinone antimalarial activities Staudinger reaction [CHIM.THER]Chemical Sciences/Medicinal Chemistry General Pharmacology Toxicology and Pharmaceutics isatin in-silico study |
| Zdroj: | Medicinal Chemistry Research Medicinal Chemistry Research, Springer Verlag, 2022, 31 (6), pp.1026-1034. ⟨10.1007/s00044-022-02898-8⟩ Medicinal Chemistry Research, 2022, 31 (6), pp.1026-1034. ⟨10.1007/s00044-022-02898-8⟩ |
| ISSN: | 1554-8120 1054-2523 |
| DOI: | 10.1007/s00044-022-02898-8 |
| Popis: | International audience; In our ongoing search for bioactive compounds, a class of novel spiro-β-lactam isatin hybrids has been synthesized through a [2 + 2] cycloaddition reaction from 1-allyl-3-(arylimino)indolin-2-one, ketenes and various aryloxy acetic acids. The formation of all cycloadducts was confirmed by FTIR, 1H NMR, 13C NMR, and mass spectroscopy as well as elemental analyses. The new β-lactams were subsequently evaluated for their biological activities demonstrating moderate to good activities against P. falciparum K1 strain. Among them, 4b and 4e lead to the best results with IC50 of 5.04 and 7.18 µM, respectively. The molecular docking simulation of 4b with P. falciparum dihydrofolate reductase enzyme (PfDHFR) binding site presented several important intermolecular interactions. All the synthesized β-lactams were also evaluated for their antimicrobial activities against both Gram-positive (S. aureus ATCC 25923) and Gram-negative bacteria (E. coli ATCC 28922, P. aeruginosa ATCC 27853) but unfortunately MICs up to 200 µg/mL were encountered in all cases. |
| Databáze: | OpenAIRE |
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