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Molecules 2012, 17(9), 10846-10863; doi:10.3390/molecules170910846
Article

Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives

1, 2, 3, 1, 4, 5, 1 and 6,*
1 School of Pharmacy, College of Pharmacy, Taipei Medical University, 250 Wuxing St., Taipei 11031, Taiwan 2 Department of Veterinary Medicine, School of Veterinary Medicine, College of Bioresources and Agriculture, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan 3 School of Respiratory Therapy, Taipei Medical University, Taipei Medical University, 250 Wuxing St., Taipei 11031, Taiwan 4 Department of Biochemistry and Chemistry, University of Washington, 4311 11th Ave. NE, Seattle, WA 98105-4068, USA 5 Research Center for Biomedical Devices and Prototyping Production, Taipei Medical University, 250 Wuxing St., Taipei 11031, Taiwan 6 Department of Microbiology and Immunology, School of Medicine, College of Medicine, Taipei Medical University, 250 Wuxing St., Taipei 11031, Taiwan
* Author to whom correspondence should be addressed.
Received: 29 June 2012 / Revised: 20 August 2012 / Accepted: 3 September 2012 / Published: 10 September 2012
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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 4ac 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 1421 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.
Keywords: 4-hydroxy-; 7-hydroxy-; 3-carboxycoumarin derivatives; antibacterial activities 4-hydroxy-; 7-hydroxy-; 3-carboxycoumarin derivatives; antibacterial activities
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Lin, P.-Y.; Yeh, K.-S.; Su, C.-L.; Sheu, S.-Y.; Chen, T.; Ou, K.-L.; Lin, M.-H.; Lee, L.-W. Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives. Molecules 2012, 17, 10846-10863.

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