Cargando…

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

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. Becaus...

Descripción completa

Detalles Bibliográficos
Autores principales: Lin, Pen-Yuan, Yeh, Kuang-Sheng, Su, Chien-Ling, Sheu, Shiow-Yunn, Chen, Tiffany, Ou, Keng-Liang, Lin, Mei-Hsiang, Lee, Lin-Wen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268400/
https://www.ncbi.nlm.nih.gov/pubmed/22964501
http://dx.doi.org/10.3390/molecules170910846
_version_ 1783376278050570240
author Lin, Pen-Yuan
Yeh, Kuang-Sheng
Su, Chien-Ling
Sheu, Shiow-Yunn
Chen, Tiffany
Ou, Keng-Liang
Lin, Mei-Hsiang
Lee, Lin-Wen
author_facet Lin, Pen-Yuan
Yeh, Kuang-Sheng
Su, Chien-Ling
Sheu, Shiow-Yunn
Chen, Tiffany
Ou, Keng-Liang
Lin, Mei-Hsiang
Lee, Lin-Wen
author_sort Lin, Pen-Yuan
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6268400
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62684002018-12-12 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 Molecules Article 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. MDPI 2012-09-10 /pmc/articles/PMC6268400/ /pubmed/22964501 http://dx.doi.org/10.3390/molecules170910846 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
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
title Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
title_full Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
title_fullStr Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
title_full_unstemmed Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
title_short Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
title_sort synthesis and antibacterial activities of novel 4-hydroxy-7-hydroxy- and 3-carboxycoumarin derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268400/
https://www.ncbi.nlm.nih.gov/pubmed/22964501
http://dx.doi.org/10.3390/molecules170910846
work_keys_str_mv AT linpenyuan synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT yehkuangsheng synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT suchienling synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT sheushiowyunn synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT chentiffany synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT oukengliang synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT linmeihsiang synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives
AT leelinwen synthesisandantibacterialactivitiesofnovel4hydroxy7hydroxyand3carboxycoumarinderivatives