Synthesis of new benzisoxazole derivatives and their antimicrobial, antioxidant and anti-inflammatory activities

Shivaprasad, Chalya Mallappaji; Jagadish, Swamy; Swaroop, Toreshettahally R.; Mohan, Chakrabhavi Dhananjaya; Roopashree, Rangaswamy; Kumar, Kothanahally S. Sharath; Rangappa, Kanchugarakoppal S.

doi:10.5155/eurjchem.5.1.91-95.866

Cited by 9 publications

(3 citation statements)

References 18 publications

(17 reference statements)

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“…Antibacterial activity was evaluated using disc diffusion method, in which compound with unsubstituted phenyl ring exhibited highest antibacterial activity. The derivatives containing 4-methyl or 2/4-nitro group showed good anti-inflammatory activity [30].…”

Section: -Fluoro-3-(piperidin-4-yl) Benzo [D] Isoxazole Derivativesmentioning

confidence: 99%

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Manjusha

Begum

et al. 2018

Asian J Pharm Clin Res

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Piperidine is a saturated heterocyclic ring, considered as a privileged scaffold in view of its role in wide range of biological activities. Piperidine is good candidate molecule for obtaining potent antioxidant agents. The planar nature of this heterocyclic nucleus allows the introduction of substituent groups at different positions on the ring. In the present review, the antioxidant profile of piperidine containing compounds has been focused. The compounds were classified into naturally occurring piperidines, unsaturated piperidines, N-substituted piperidines, piperamides, piperanols, piperidine oximes, and hydrazides.

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Section: -Fluoro-3-(piperidin-4-yl) Benzo [D] Isoxazole Derivativesmentioning

confidence: 99%

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Manjusha

Begum

et al. 2018

Asian J Pharm Clin Res

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“…Chaker et al 44 synthesized a new series of 3-substituted-2,1-benzisoxazole (anthranils) analogs and evaluated them for their in vitro antibacterial activity against representative Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas aeruginosa and Cronobacter sakazakii) and against two fungal (Geotrichum candidum and Candida albicans) strains. The antimicrobial activities of all the synthesized compounds were determined, and among them, compounds 29-31 ( Shivaprasad et al 45 synthesized a series of novel benzisoxazole derivatives and tested them for their antibacterial, antioxidant and anti-inflammatory activities. Compound 32, a benzisoxazole derivative without substitution on the phenyl ring, showed good antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Salmonella typhi and Bacillus subtilis.…”

Section: Antimicrobial Activitiesmentioning

confidence: 99%

Benzisoxazole: a privileged scaffold for medicinal chemistry

Rakesh

Shantharam²,

Sridhara

et al. 2017

Med. Chem. Commun.

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The benzisoxazole analogs represent one of the privileged structures in medicinal chemistry and there has been an increasing number of studies on benzisoxazole-containing compounds. The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on. This review examines the state of the art in medicinal chemistry as it relates to the comprehensive and general summary of the different benzisoxazole analogs, their use as starting building blocks of multifarious architectures on scales sufficient to drive human drug trials. The number of reports describing benzisoxazole-containing highly active compounds leads to the expectation that this scaffold will further emerge as a potential candidate in the field of drug discovery.

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“…Although uncommonly reported from natural sources, benzisoxazole scaffolds are well represented in pharmacology, having shown significant importance in anti-HIV [14], antimicrobial [15][16][17][18], antipsychotic [19,20], antiinflammatory [17,21,22], antioxidation [17,23], anticancer [23][24][25][26], anticonvulsant [27] and antidiabetic [28,29] research. Moreover, 1,2-benzisoxazole derivatives, which include zonisamide, risperidone, paliperidone, and iloperidone, are all FDA approved and currently in use for epilepsy, mood disorders, and schizophrenia, respectively [30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Identification of a bacteria-produced benzisoxazole with antibiotic activity against multi-drug resistant Acinetobacter baumannii

et al. 2021

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The emergence of multi-drug resistant pathogenic bacteria represents a serious and growing threat to national healthcare systems. Most pressing is an immediate need for the development of novel antibacterial agents to treat Gram-negative multi-drug resistant infections, including the opportunistic, hospital-derived pathogen, Acinetobacter baumannii. Herein we report a naturally occurring 1,2-benzisoxazole with minimum inhibitory concentrations as low as 6.25 μg ml−1 against clinical strains of multi-drug resistant A. baumannii and investigate its possible mechanisms of action. This molecule represents a new chemotype for antibacterial agents against A. baumannii and is easily accessed in two steps via de novo synthesis. In vitro testing of structural analogs suggest that the natural compound may already be optimized for activity against this pathogen. Our results demonstrate that supplementation of 4-hydroxybenzoate in minimal media was able to reverse 1,2-benzisoxazole’s antibacterial effects in A. baumannii. A search of metabolic pathways involving 4-hydroxybenzoate coupled with molecular modeling studies implicates two enzymes, chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyltransferase, as promising leads for the target of 3,6-dihydroxy-1,2-benzisoxazole.

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Synthesis of new benzisoxazole derivatives and their antimicrobial, antioxidant and anti-inflammatory activities

Cited by 9 publications

References 18 publications

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Benzisoxazole: a privileged scaffold for medicinal chemistry

Identification of a bacteria-produced benzisoxazole with antibiotic activity against multi-drug resistant Acinetobacter baumannii

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