Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of 7-Hydroxy-4-methylcoumarin Derivatives 5a–h
2.2. Determination of the in Vitro Antimicrobial Activity
Bacteria | Conc. | X | |||||||
---|---|---|---|---|---|---|---|---|---|
4-N(CH3)2 (5a) | 4-OH (5b) | 4-OCH3 (5c) | 4-H (5d) | 4-Br (5e) | 4-Cl (5f) | 2-NO2 (5g) | 4-NO2 (5h) | ||
d (mm) a | |||||||||
Escherichia coli | 0.1% | 14 | 15 | 13 | 14 | 15 | 12 | 12 | 15 |
0.2% | 16 | 17 | 16 | 16 | 16 | 15 | 15 | 18 | |
Pseudomonas aeruginosa | 0.1% | 13 | 19 | 12 | 17 | 15 | 15 | 14 | 18 |
0.2% | 15 | 23 | 15 | 19 | 18 | 17 | 16 | 20 | |
Bacillus subtilis | 0.1% | 15 | 15 | 14 | 15 | 18 | 14 | 13 | 14 |
0.2% | 17 | 19 | 16 | 18 | 21 | 18 | 16 | 17 | |
Staphylococcus aureus | 0.1% | 13 | 14 | 14 | 16 | 17 | 14 | 15 | 16 |
0.2% | 15 | 16 | 18 | 17 | 20 | 16 | 17 | 18 |
Bacteria | MIC (μg/mL) | |||||||
---|---|---|---|---|---|---|---|---|
4-N(CH3)2 (5a) | 4-OH (5b) | 4-OCH3 (5c) | 4-H (5d) | 4-Br (5e) | 4-Cl (5f) | 2-NO2 (5g) | 4-NO2 (5h) | |
Escherichia coli | - a | - | - | - | - | - | - | - |
P. aeruginosa | - | - | - | - | - | - | - | - |
Bacillus subtilis | - | - | - | - | - | - | - | - |
Staphylococcus aureus | - | - | 50 | - | - | - | 50 | 50 |
3. Experimental Section
3.1. General Procedures
3.2. Synthesis of 7-Hydroxy-4-methylcoumarin Derivatives 5a–h
3.2.1. Synthesis of 4-Oxo-2-thioxothiazolidine Derivatives
3.2.2. Synthesis of 2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-oxo-2-thioxothiazo-lidin-3-yl)aceta-mide (4)
3.2.3. General Procedure for Synthesis of N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetamides 5a–h
3.3. Determination of the in Vitro Antimicrobial Activity
3.4. Minimum Inhibitory Concentration (MIC) Determination
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Cong, N.T.; Nhan, H.T.; Van Hung, L.; Thang, T.D.; Kuo, P.-C. Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one. Molecules 2014, 19, 13577-13586. https://doi.org/10.3390/molecules190913577
Cong NT, Nhan HT, Van Hung L, Thang TD, Kuo P-C. Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one. Molecules. 2014; 19(9):13577-13586. https://doi.org/10.3390/molecules190913577
Chicago/Turabian StyleCong, Nguyen Tien, Huynh Thi Nhan, Luong Van Hung, Tran Dinh Thang, and Ping-Chung Kuo. 2014. "Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one" Molecules 19, no. 9: 13577-13586. https://doi.org/10.3390/molecules190913577