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

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

1, 2, 3, 1, 4, 5, 1 and 6,*
Received: 29 June 2012 / Revised: 20 August 2012 / Accepted: 3 September 2012 / Published: 10 September 2012
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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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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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