Synthesis and Antimicrobial Activity of Some New Spiropyrazoline Derivatives of 9α‐ and 9β‐Hydroxyparthenolide

• Published in: ChemistrySelect (Weinheim) 2022-03, Vol.7 (11), p.n/a
• Main Authors: Moumou, Mohamed, Outahar, Fatima, Ourhzif, El‐Mahdi, Hannioui, Abdellah, Bouamama, Hafida, El Ammari, Lahcen, Saadi, Mohamed, Rakib, El Mostapha, Akssira, Mohamed
• Format: Article
• Language: English
• Subjects: Antimicrobial activity; Anvillea radiata; Escherichia coli; Spiropyrazoline; Synthesis
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202104040

In the present study, we efficiently synthesized two new series of spiropyrazoline derivatives from 9α‐ and 9β‐hydroxyparthenolide (isolated from the aerial parts of Anvillea radiata). The compounds were obtained by modifications at the C−13 and C−9 positions via 1,3‐dipolar cycloaddition followed by O−H acylation at the C1−C10 using epoxidation with metachloroperoxybenzoic acid (m‐CPBA) followed by 1,3‐dipolar cycloaddition on the double bond α‐methylene‐γ‐lactones. The structures and stereochemistry of the cycloadducts were established by spectroscopic methods, including X‐ray diffraction data. Some compounds were tested for antibacterial activity. Several spiropyrazoline derivatives showed good to moderate activity against bacteria. This manuscript report the synthesis and antibacterial activity of new spiropyrazoline derivatives from the natural hydroxyparthenolide 9α‐ and 9β‐ (isolated from the aerial parts of Anvillea radiata). The structures and stereochemistry of the new spiropyrazoline derivatives were established by spectroscopic methods, including X‐ray diffraction data. Their biological activities were evaluated against some bacterial strains and showed good to moderate activity against Escherichia coli and Pseudomonas aeruginosa.