In the present investigation, 17 new synthetic butenolides, i.e. 2-arylidene-4-(4-chloro/ethyl-phenyl)but-3-en-4-olides (3-19) have been synthesized from 3-(4-chloro-benzoyl)propionic acid or 3-(4-ethyl-benzoyl)propionic acid using appropriate reagents. Some of the selected butenolides were reacted with ammonia and benzylamine to give the corresponding pyrrolones (20-31) and N-benzyl-pyrrolones (32-39) respectively. All the compounds were screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against Candida albicans, Aspergillus niger, and Rhizopus oryza. Minimum inhibitory concentration (MIC) values of the compounds are reported. The pyrrolone derivatives discovered in this study may provide valuable therapeutic intervention for the treatment of microbial diseases, especially against fungal species.
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http://dx.doi.org/10.3109/14756360902940860 | DOI Listing |
Org Biomol Chem
December 2024
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721032, India.
Herein, we disclose the asymmetric total synthesis of 1'-deshydroxymethyl analogues of naturally occurring aporpinone A, aporpinone B, and 4'-hydroxyaporpinone A, featuring a γ--alkylidene butenolide framework. Bimetallic (Pd-Cu) cascade cyclization on a properly functionalized bis-alkyne with -2-bromoacrylic acid was employed to construct the butenolide framework with an alkyne appendage. Late-stage enzymatic kinetic resolution (EKR) was adopted for the synthesis of ()-1'-deshydroxymethyl aporpinone A and ()-1'-deshydroxymethyl acetyl aporpinone A.
View Article and Find Full Text PDFJ Nat Prod
September 2024
Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901 Belo Horizonte, MG, Brazil.
Rubrolides are a family of naturally occurring 5-benzylidenebutenolides, which generally contain brominated phenol groups, and nearly half of them also present a chlorine attached to the butenolide core. Seven natural rubrolides were previously synthesized. When these compounds were tested against the model plant , six were found to exert a slight inhibition on plant growth.
View Article and Find Full Text PDFJ Org Chem
September 2024
Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.
Herein, we present two unprecedented reactions for the synthesis of γ-butenolides and oxazoles, leveraging TfO's promoted reactivity of nitriles with diacetonide endoglucofuranose and 1,2,3,5-tetra--acetyl-β-d-ribofuranose. This method is highly efficient and straightforward and employs a one-step, metal-free protocol. It is effective with both aromatic and aliphatic nitriles and demonstrates a broad substrate scope.
View Article and Find Full Text PDFJ Nat Prod
August 2024
Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90110, Thailand.
Total syntheses of two γ-butenolide natural products, asperjinone () and asperimide C () in both racemic and chiral forms have been accomplished utilizing Basavaiah's one-pot Friedel-Crafts/maleic anhydride formation protocol as a key strategy. Our syntheses verified the revised structure of proposed by Williams et al. and the structure and absolute configuration of reported by the Li group.
View Article and Find Full Text PDFOrg Lett
June 2024
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 11677.
The first enantioselective vinylogous Mannich reaction is developed using 2-methoxyfuran under chiral spirophosphoric acid catalysis. The strategy involves 4-isoxazoline derivatives as cyclic ketimine surrogates and provides γ-butenolide scaffolds (up to 97% ee and >20:1 dr). The mechanistic investigations suggest that an generated water molecule plays a crucial role in delivering γ-butenolide, while the use of molecular sieves delivers -Friedel-Crafts products.
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