Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of 1-Alkyl-3-methacryloyl (Acryloyl)-benzimidazolone (Thione)
2.2. Antibacterial Activities
3. Experimental Section
3.1. General Experimental Procedures
3.2. Synthetic Procedures
3.2.1. General Procedures for 1-Alkyl-Benzimidazolone (Thione) (2)
3.2.2. General Procedures for 1-Alkyl-3-Methacryloyl (Acryloyl)-Benzimidazolone (Thione) (3)
3.3. Antibacterial Activity
3.4. Minimum Inhibitory Concentrations (MICs)
4. Conclusions
Acknowledgments
References
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Compounds | Zone of inhibition (mm) | ||||
---|---|---|---|---|---|
B. cereus | B. subtilis | E. coli | S. aureus | P. aeruginosa | |
3aI (1-alkyl-3-methacryloyl-benzimidazolone) | |||||
1 | 14(+++) | 13(+++) | 19(+++) | 11(++) | 15(+++) |
2 | 13(+++) | 15(+++) | 18(+++) | 11(++) | 14(+++) |
3 | 15(+++) | 15(+++) | 19(+++) | - | 20(+++) |
4 | 13(+++) | 14(+++) | 17(+++) | - | 16(+++) |
5 | 10(++) | 12(++) | 14(++) | 10(+) | 9(++) |
6 | 14(+++) | 16(+++) | 19(+++) | 14(++) | 16(+++) |
7 | - | - | - | - | - |
3aII (1-alkyl-3-acryloyl-benzimidazolone) | |||||
1 | 6(+) | 7(+) | 11(+) | - | - |
2 | 7(+) | 7(+) | - | - | - |
3 | 7(+) | - | - | - | - |
4 | - | - | - | - | - |
5 | 10 | 8 | - | - | - |
6 | 7 | - | - | - | - |
7 | - | - | - | - | - |
3bI (1-alkyl-3-methacryloyl-benzimidazolthione) | |||||
1 | 13(+++) | 13(+++) | 15(+++) | 13(++) | 14(+++) |
2 | 12(+++) | 13(+++) | 19(+++) | 11(++) | 14(+++) |
3 | 14(+++) | 14(+++) | 18(+++) | 9(+) | 20(+++) |
4 | 12(+++) | 13(+++) | 17(+++) | - | 15(+++) |
5 | 9(++) | 8(+) | 10(++) | 9(+) | 9(++) |
6 | 12(+++) | 11(+++) | 15(+++) | 12(+) | 16(+++) |
7 | - | - | - | - | - |
3bII (1-alkyl-3-acryloyl-benzimidazolthione) | |||||
1 | 6(+) | 6(+) | - | - | - |
2 | 6(+) | - | 12(+) | - | - |
3 | 7(+) | - | - | - | - |
4 | - | - | - | - | - |
5 | - | - | - | - | - |
6 | 7(+) | - | - | - | - |
7 | - | - | - | - | - |
Ampicillin | 15(+++) | 16(+++) | 18(+++) | 13(++) | 20(+++) |
Compounds | MICs (μg/mL) | ||||
---|---|---|---|---|---|
B. cereus | B. subtilis | E. coli | S. aureus | P. aeruginosa | |
3aI (1-alkyl-3-methacryloyl-benzimidazolone) | |||||
1 | 6.25 | 3.13 | 3.13 | 25 | 25 |
2 | 12.5 | 1.56 | 6.25 | 50 | 25 |
3 | 3.13 | 3.13 | 1.56 | >100 | 12.5 |
4 | 12.5 | 6.25 | 12.5 | >100 | 50 |
5 | 100 | 100 | >100 | >100 | >100 |
6 | 6.25 | 12.5 | 1.56 | 12.5 | 50 |
3bI (1-alkyl-3-methacryloyl-benzimidazolthione) | |||||
1 | 12.5 | 6.25 | 12.5 | 50 | 25 |
2 | 12.5 | 3.13 | 6.25 | 50 | 25 |
3 | 3.13 | 6.25 | 3.13 | >100 | 25 |
4 | 25 | 12.5 | 6.25 | >100 | 50 |
5 | >100 | >100 | >100 | >100 | >100 |
6 | 12.5 | 25 | 3.13 | 25 | 100 |
Ampicillin | 6.25 | 1.56 | 3.13 | 6.25 | 25 |
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Wei, S.; Wu, W.; Ji, Z. Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives. Int. J. Mol. Sci. 2012, 13, 4819-4830. https://doi.org/10.3390/ijms13044819
Wei S, Wu W, Ji Z. Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives. International Journal of Molecular Sciences. 2012; 13(4):4819-4830. https://doi.org/10.3390/ijms13044819
Chicago/Turabian StyleWei, Shaopeng, Wenjun Wu, and Zhiqin Ji. 2012. "Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives" International Journal of Molecular Sciences 13, no. 4: 4819-4830. https://doi.org/10.3390/ijms13044819
APA StyleWei, S., Wu, W., & Ji, Z. (2012). Synthesis and Antibacterial Activities of 1-Alkyl-3-methacryloyl (Acryloyl) of Benzimidazolone (Thione) Derivatives. International Journal of Molecular Sciences, 13(4), 4819-4830. https://doi.org/10.3390/ijms13044819