Synthesis and antibacterial activities of novel 4-hydroxy-7-hydroxy- and 3-carboxycoumarin derivatives

Pen Yuan Lin, Kuang Sheng Yeh, Chien Ling Su, Shiow Yunn Sheu, Tiffany Chen, Keng Liang Ou, Mei Hsiang Lin, Lin Wen Lee

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 coumarinsubstituted 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.

Original languageEnglish
Pages (from-to)10846-10863
Number of pages18
JournalMolecules
Volume17
Issue number9
DOIs
Publication statusPublished - Sep 2012

Fingerprint

Umbelliferones
antibiotics
physiological effects
anticoagulants
dimers
Derivatives
4-Hydroxycoumarins
infectious diseases
microorganisms
anhydrides
synthesis
Aziridines
medicine
Dimers
Dicumarol
amides
Anti-Bacterial Agents
Coumarins
drugs
Aflatoxins

Keywords

  • 3-carboxycoumarin derivatives
  • 4-hydroxy-
  • 7-hydroxy-
  • Antibacterial activities

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Synthesis and antibacterial activities of novel 4-hydroxy-7-hydroxy- and 3-carboxycoumarin derivatives. / Lin, Pen Yuan; Yeh, Kuang Sheng; Su, Chien Ling; Sheu, Shiow Yunn; Chen, Tiffany; Ou, Keng Liang; Lin, Mei Hsiang; Lee, Lin Wen.

In: Molecules, Vol. 17, No. 9, 09.2012, p. 10846-10863.

Research output: Contribution to journalArticle

Lin, Pen Yuan ; Yeh, Kuang Sheng ; Su, Chien Ling ; Sheu, Shiow Yunn ; Chen, Tiffany ; Ou, Keng Liang ; Lin, Mei Hsiang ; Lee, Lin Wen. / Synthesis and antibacterial activities of novel 4-hydroxy-7-hydroxy- and 3-carboxycoumarin derivatives. In: Molecules. 2012 ; Vol. 17, No. 9. pp. 10846-10863.
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