Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antibacterial Evaluation
2.3. SAR Studies
3. Experimental Section
3.1. General Information
3.2. Synthesis
3.2.1. Starting Materials
3.2.2. General Procedure for the Synthesis of Compounds 7a–c
3.2.3. General Procedure for the Preparation of Compounds 7d–f
3.2.4. General Procedure for the Preparation of Compounds 7g–i
3.2.5. General Procedure for the Preparation of Compounds 7j–l
3.2.6. General Procedure for the Preparation of Compounds 7m–o
3.2.7. General Procedure for the Preparation of Compounds 8a–c
3.2.8. Synthesis of Compounds 12a–c
3.3. Antimicrobial Assay
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compound | R | Ar | S. aureus (+ve) | S. Epider. (+ve) | B. Subtilis (+ve) | B. pumilus (+ve) | P. Aerug. (−ve) | E. coli (−ve) | A. fumig. | C. albic. | S. cerev. |
---|---|---|---|---|---|---|---|---|---|---|---|
7a | H | 4-FC6H5 | NA | 11.9 ± 0.3 | NA | NA | NA | NA | NA | NA | NA |
7b | H | 4-ClC6H5 | NA | 20.5 ± 0.2 | NA | NA | NA | NA | NA | NA | NA |
7c | H | 4-BrC6H5 | NA | 23.5 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7d | CH3 | 4-FC6H5 | NA | 21.1 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7e | CH3 | 4-ClC6H5 | NA | 23.5 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7f | CH3 | 4-BrC6H5 | NA | 24.3 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7g | CO2Et | 4-FC6H5 | NA | 18.9 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7h | CO2Et | 4-ClC6H5 | NA | 17.2 ± 0.2 | NA | NA | NA | NA | NA | NA | NA |
7i | CO2Et | 4-BrC6H5 | NA | 16.1 ± 0.3 | NA | NA | NA | NA | NA | NA | NA |
7j | CH2CN | 4-FC6H5 | 27.3 ± 0.5 | 25.2 ± 0.1 | 12.3 ± 0.3 | 12.3 ± 0.3 | 28.3 ± 0.07 | 26.7 ± 0.1 | 12.3 ± 0.3 | 19.3 ± 0.1 | 23.3 ± 0.1 |
7k | CH2CN | 4-ClC6H5 | 28.8 ± 0.1 | 26.3 ± 0.3 | 12.2 ± 0.4 | 12.2 ± 0.4 | 28.2 ± 0.03 | 26.8 ± 0.3 | 12.2 ± 0.1 | 21.2 ± 0.2 | 20.2 ± 0.1 |
7l | CH2CN | 4-BrC6H5 | 29.1 ± 0.2 | 26.9 ± 0.3 | 12.7 ± 0.4 | 12.8 ± 0.4 | 28.9 ± 0.03 | 27.8 ± 0.3 | 12.1 ± 0.2 | 21.1 ± 0.2 | 18.2 ± 0.1 |
7m | Ph | 4-FC6H5 | NA | 19.3 ± 0.5 | NA | NA | NA | NA | NA | NA | NA |
7n | Ph | 4-ClC6H5 | NA | 20.9 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
7o | Ph | 4-BrC6H5 | NA | 21.4 ± 0.1 | NA | NA | NA | NA | NA | NA | NA |
8a | - | 4-FC6H5 | 21.8 ± 0.1 | 22.9 ± 0.1 | 23.1 ± 0.2 | 24.0 ± 0.3 | 19.3 ± 0.1 | 21.9 ± 0.1 | 23.8 ± 0.1 | 22.9 ± 0.1 | 16.8 ± 0.4 |
8b | - | 4-ClC6H5 | 24.6 ± 0.2 | 25.7 ± 0.2 | 25.1 ± 0.4 | 23.6 ± 0.1 | 21.3 ± 0.2 | 21.0 ± 0.4 | 23.4 ± 0.1 | 22.4 ± 0.1 | 18.2 ± 0.3 |
8c | - | 4-BrC6H5 | 26.6 ± 0.1 | 28.5 ± 0.3 | 25.1 ± 0.4 | 21.3 ± 0.1 | 23.3 ± 0.1 | 20.7 ± 0.2 | 22.1 ± 0.1 | 21.7 ± 0.2 | 19.5 ± 0.1 |
12a | - | 4-FC6H5 | NA | NA | NA | NA | NA | NA | NA | NA | NA |
12b | - | 4-ClC6H5 | NA | NA | NA | NA | NA | NA | NA | NA | NA |
12c | - | 4-BrC6H5 | NA | NA | NA | NA | NA | NA | NA | NA | NA |
Ampicillin | - | - | 27.4 ± 0.1 | 28.6 ± 0.5 | 29.4 ± 0.7 | 29.9 ± 0.3 | 26.3 ± 0.3 | 28.5 ± 0.1 | - | - | - |
Streptomycin | - | - | 25.1 ± 0.2 | 29.1 ± 0.3 | 30.1 ± 0.9 | 30.8 ± 0.4 | 24.3 ± 0.8 | 25.6 ± 0.4 | - | - | - |
Mycostatine | - | - | - | - | - | - | - | - | 29.5 ± 0.1 | 27.1 ± 0.1 | 24.1 ± 0.3 |
Clotrimazole | - | - | - | - | - | - | - | - | 26.1 ± 0.1 | 23.1 ± 0.3 | 18.3 ± 0.1 |
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Okasha, R.M.; Albalawi, F.F.; Afifi, T.H.; Fouda, A.M.; Al-Dies, A.-A.M.; El-Agrody, A.M. Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives. Molecules 2016, 21, 1450. https://doi.org/10.3390/molecules21111450
Okasha RM, Albalawi FF, Afifi TH, Fouda AM, Al-Dies A-AM, El-Agrody AM. Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives. Molecules. 2016; 21(11):1450. https://doi.org/10.3390/molecules21111450
Chicago/Turabian StyleOkasha, Rawda M., Fawzia F. Albalawi, Tarek H. Afifi, Ahmed M. Fouda, Al-Anood M. Al-Dies, and Ahmed M. El-Agrody. 2016. "Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives" Molecules 21, no. 11: 1450. https://doi.org/10.3390/molecules21111450