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Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids
- Source :
- European journal of medicinal chemistry. 117
- Publication Year :
- 2016
-
Abstract
- A series of novel diaziridinyl quinone isoxazole hybrids (9a-9j) were synthesized starting from 2, 5-dimethoxy acetophenone 1 via Claisen reaction, cyclisation, alkoxy carbonylation, hydrolysis, oxidation and aziridine insertion. All the compounds were screened for antimicrobial, anti-biofilm and cytotoxic activities. Among the screened compounds, the compound 9h showed good antibacterial and anti-biofilm activities with MIC value of 3.9, 3.9, 3.9 and 7.8 μg/mL, respectively, and IC50 values of 1.9, 2.5, 2.8 and 5.1 μM, respectively, against Staphylococcus aureus MTCC 96, S. aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Klebsiella planticola MTCC 530, and also exhibited potent antifungal activity against Candida albicans MTCC 227, C. albicans MTCC 854 and Candida krusei MTCC 3020 equipotent to standard miconazole (MIC value 7.8 μg/mL). All the synthesized compounds exhibited promising cytotoxicity against A549 and PC3 cell lines (IC50 values between 1 and 4 μM). Compounds 9b and 9j exhibited IC50 value of 0.5 μM which was similar to that of Mitomycin C against PC3 cell line.
- Subjects :
- Antifungal Agents
Stereochemistry
Bacillus subtilis
Microbial Sensitivity Tests
010402 general chemistry
01 natural sciences
chemistry.chemical_compound
Anti-Infective Agents
Candida krusei
Cell Line, Tumor
Drug Discovery
medicine
Humans
Isoxazole
Candida albicans
Pharmacology
biology
010405 organic chemistry
Cytotoxins
Organic Chemistry
Quinones
General Medicine
Isoxazoles
Antimicrobial
biology.organism_classification
0104 chemical sciences
Quinone
Anti-Bacterial Agents
chemistry
A549 Cells
Biofilms
Miconazole
Antibacterial activity
medicine.drug
Subjects
Details
- ISSN :
- 17683254
- Volume :
- 117
- Database :
- OpenAIRE
- Journal :
- European journal of medicinal chemistry
- Accession number :
- edsair.doi.dedup.....775e2fa715ae43ccbee1d12af67a3263