Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Activity
2.3. Identification of Antimicrobial Pharmacophore Sites of 1–10
3. Experimental Section
3.1. General
3.2. General Procedure for the Synthesis of Compounds 1–10
3.2.1. Procedure A
3.2.2. Procedure B
3.2.2.1. 2-Amino-N-(4-fluorophenyl)benzamide (1)
3.2.2.2. 2-Amino-N-(4-chlorophenyl)benzamide (2)
3.2.2.3. 2-[4-(2-Aminobenzamido)phenyl]acetic acid (3)
3.2.2.4. 2-Amino-N-(3,4-dimethoxyphenyl)benzamide (4)
3.2.2.5. 2-Amino-N-(4-methoxyphenyl)benzamide (5)
3.2.2.6. 2-Amino-N-(3,4,5-trimethoxyphenyl)benzamide (6)
3.2.2.7. 2-Amino-N-(p-tolyl)benzamide (7)
3.2.2.8. 2-Amino-N-(2-carbamoylphenyl)benzamide (8)
3.2.2.9. 2-Amino-N-(4-chlorobenzyl)benzamide (9)
3.2.2.10. 2-Amino-N-(3,4-dimethoxyphenethyl)benzamide (10)
4. Antifungal Activity
5. Antibacterial Activity
6. Conclusions
Acknowledgments
Conflicts of Interest
- Author ContributionsYahia N. Mabkhot designed the study, carried out the synthesis; Abdullah M. Al-Majid designed the study, carried out the synthesis. Assem Barakat wrote some research and audit. Salim S. Al-Showiman wrote some research and audit. Munirah S. Al-Har student did the experiments. Smaail Radi carried out Petra analyses. Muhammad Moazzam Naseer edited the English language. Taibi B. Hadda carried out and compiled Petra/Osiris/Molinspiration (POM) analyses with comparison to experimental data.
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Compound | Bacteria | Fungi | |||||
---|---|---|---|---|---|---|---|
(A) [a] | (B) [a] | (C) [b] | (D) [b] | (E) | (F) | (G) | |
1 | 9.9 | 9.7 | 9.1 | 9.4 | 11.8 | 11.2 | 11.9 |
2 | 7.2 | 7.8 | 7.4 | 6.9 | 9.4 | 8.2 | 8.4 |
3 | 11.9 | 11.1 | 10.4 | 9.5 | 11.8 | 11.5 | 11.2 |
5 | 17.9 | 19.2 | 10.9 | 12.4 | 19.7 | 20.1 | 15.8 |
7 | 9.1 | 8.8 | 7.9 | 7.6 | 12.2 | 9.4 | 7.2 |
CLOZO [c] | - | - | - | - | 18.3 | 23.1 | 26.1 |
STREPT [d] | 25.1 | 30.1 | 25.6 | 24.3 | - | - | - |
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Mabkhot, Y.N.; Al-Majid, A.M.; Barakat, A.; Al-Showiman, S.S.; Al-Har, M.S.; Radi, S.; Naseer, M.M.; Hadda, T.B. Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site. Int. J. Mol. Sci. 2014, 15, 5115-5127. https://doi.org/10.3390/ijms15035115
Mabkhot YN, Al-Majid AM, Barakat A, Al-Showiman SS, Al-Har MS, Radi S, Naseer MM, Hadda TB. Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site. International Journal of Molecular Sciences. 2014; 15(3):5115-5127. https://doi.org/10.3390/ijms15035115
Chicago/Turabian StyleMabkhot, Yahia N., Abdullah M. Al-Majid, Assem Barakat, Salim S. Al-Showiman, Munirah S. Al-Har, Smaail Radi, Muhammad Moazzam Naseer, and Taibi B. Hadda. 2014. "Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site" International Journal of Molecular Sciences 15, no. 3: 5115-5127. https://doi.org/10.3390/ijms15035115