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Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
- Source :
- Molecules, Vol 17, Iss 9, Pp 10846-10863 (2012), Molecules; Volume 17; Issue 9; Pages: 10846-10863, Molecules
- Publication Year :
- 2012
- Publisher :
- MDPI AG, 2012.
-
Abstract
- Coumarin derivatives are used as fluorescent dyes and medicines. They also have some notable physiological effects, including the acute hepatoxicity and carcinogenicity of certain aflatoxins, the anticoagulant action of dicoumarol, and the antibiotic activity of novobicin and coumerymycin A1. Because the number of drug resistant strains is increasing at present, the synthesis of new antibacterial compounds is one of the critical methods for treating infectious diseases. Therefore, a series of coumarin-substituted derivatives, namely 4-hydroxy- and 7-hydroxycoumarins, and 3-carboxycoumarins were synthesized. 4-Hydroxycoumarin derivatives 4a–c underwent rearrangement reactions. Both 4- and 7-hydroxycoumarins were treated with activated aziridines which produced series of ring-opened products 7, 8, 10, and 11. 3-Carboxy-coumarin amide dimer derivatives 14–21 were prepared by reacting aliphatic alkylamines and alkyldiamines with PyBOP and DIEA. In this study, we use a new technique called modified micro-plate antibiotic susceptibility test method (MMAST), which is more convenient, more efficient, and more accurate than previous methods and only a small amount of the sample is required for the test. Some of the compounds were produced by reactions with acid anhydrides and demonstrated the ability to inhibit Gram-positive microorganisms. The dimer derivatives displayed lower antibacterial activities.
- Subjects :
- Staphylococcus aureus
Aflatoxin
medicine.drug_class
Dimer
Antibiotics
4-hydroxy
Pharmaceutical Science
Microbial Sensitivity Tests
Article
7-hydroxy
Analytical Chemistry
lcsh:QD241-441
Structure-Activity Relationship
chemistry.chemical_compound
lcsh:Organic chemistry
Coumarins
3-carboxycoumarin derivatives
antibacterial activities
Amide
Drug Discovery
Escherichia coli
medicine
Organic chemistry
Umbelliferones
Physical and Theoretical Chemistry
Carcinogen
Bacteria
Organic Chemistry
4-Hydroxycoumarins
Dicoumarol
Coumarin
Anti-Bacterial Agents
PyBOP
chemistry
Chemistry (miscellaneous)
Pseudomonas aeruginosa
Molecular Medicine
Bacillus subtilis
medicine.drug
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 17
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....e6d2eb16bc56f6f33f338a4f7213b358