Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.1.1. Preparation of the Chalcones 2–4
2.1.2. Synthesis of Pyrazoline Derivatives 5–9 and Isoxazoline Derivatives 10–12
2.1.3. Synthesis of Benzenesulfonamide Derivatives 13–21
2.1.4. Synthesis of [1,2,4]Triazolo[3,4-c][1,2,4]triazino[5,6-b]-5-N-(phenylcarbamothioyl) Ethanoic Acid Hydrazide Derivatives 30, 31 and 3-Methyl-4-(propan-2-ylidene)-1H-pyrazol-5(4H)-one Derivatives 34, 35
2.1.5. Synthesis of Schiff’s Bases 36, 37, 4-Oxo-4,5,6,7-tetrahydro-1H-indol-2-yl)thiazolidin-4-one (38), Benzohydrazide Derivative 39, 1,2,4]Triazolo[3,4-c]-5,10-dihydro [1,2,4]triazino[5,6-b] quinoxaline (40), and Pyrazole Derivatives 41–44
2.2. Pharmacological Screening
Microorganism | Escherichia coli | Staphylococcus aureus | Candida albicans | Pseudomonas aeruginosa | ||||
---|---|---|---|---|---|---|---|---|
IZ | MIC | IZ | MIC | IZ | MIC | IZ | MIC | |
ampicillin 10.0 µg/disc | 18 | 25 | 22 | 12.5 | ----- | ------ | ----- | ----- |
ciprofloxacin 5.0 µg/disc | 28 | 12.5 | 30 | 25 | ----- | ------ | 38 | 25 |
clotrimazole 100.0 µg/disc | ---- | ----- | ----- | ------ | 40 | 12.5 | ----- | ------ |
imipenam 10.0 µg/disc | 26 | ----- | 30 | ------ | ----- | ---- | 30 | ------ |
2 | 18 | 200 | 17 | 200 | 21 | 200 | 16 | 200 |
3 | 19 | 200 | 17 | 200 | 24 | 200 | 18 | 200 |
4 | 19 | 200 | 15 | 200 | 23 | 200 | 18 | 200 |
5 | 19 | 200 | 15 | 200 | 23 | 200 | 19 | 200 |
6 | 19 | 200 | 16 | 200 | 25 | 200 | 20 | 200 |
7 | 18 | 200 | 13 | 200 | 21 | 200 | 16 | 200 |
8 | 19 | 200 | 17 | 200 | 22 | 200 | 18 | 200 |
9 | 18 | 200 | 16 | 200 | 24 | 200 | 18 | 200 |
10 | 19 | 200 | 16 | 200 | 24 | 200 | 20 | 200 |
11 | 19 | 200 | 18 | 100 | 23 | 200 | 19 | 200 |
12 | 19 | 200 | 15 | 200 | 23 | 200 | 18 | 200 |
13 | 18 | 200 | 19 | 200 | 23 | 200 | 18 | 200 |
14 | 18 | 200 | 15 | 200 | 23 | 200 | 18 | 200 |
15 | 18 | 200 | 16 | 100 | 22 | 200 | 19 | 200 |
16 | 19 | 200 | 26 | 25 | 27 | 50 | 20 | 200 |
17 | 19 | 200 | >50 | 100 | >40 | 50 | 21 | 100 |
18 | 19 | 200 | 20 | 100 | 23 | 200 | 19 | 200 |
19 | 19 | 200 | 16 | 100 | 25 | 12.5 | 19 | 200 |
20 | 18 | 200 | 16 | 200 | 26 | 12.5 | 18 | 200 |
21 | 18 | 200 | 16 | 200 | 28 | 50 | 20 | 200 |
22 | 19 | 200 | 16 | 200 | 25 | 50 | 18 | 200 |
23 | 18 | 200 | 8 | 200 | 24 | 200 | 20 | 200 |
24 | 18 | 200 | 16 | 200 | 23 | 200 | 20 | 200 |
25 | 19 | 200 | 15 | 200 | 22 | 200 | 18 | 200 |
26 | 19 | 200 | 13 | 200 | 23 | 200 | 19 | 200 |
27 | 19 | 200 | 17 | 200 | 25 | 200 | 17 | 200 |
28 | 19 | 200 | 17 | 200 | 23 | 200 | 18 | 200 |
29 | 18 | 200 | 15 | 200 | 21 | 200 | 18 | 200 |
30 | 19 | 200 | 17 | 200 | 26 | 200 | 16 | 200 |
31 | 19 | 200 | 16 | 200 | 34 | 25 | 20 | 200 |
32 | 19 | 200 | 16 | 200 | 23 | 200 | 20 | 200 |
33 | 19 | 200 | 17 | 200 | 24 | 200 | 18 | 200 |
34 | 19 | 200 | 17 | 200 | 24 | 200 | 17 | 200 |
35 | 19 | 200 | 16 | 100 | 23 | 200 | 19 | 200 |
36 | 19 | 200 | 17 | 200 | 24 | 200 | 18 | 200 |
37 | 17 | 200 | 15 | 200 | 22 | 200 | 18 | 200 |
38 | 19 | 200 | 17 | 200 | 21 | 200 | 18 | 200 |
39 | 19 | 200 | 17 | 200 | 22 | 200 | 16 | 200 |
40 | 19 | 200 | 17 | 200 | 21 | 200 | 18 | 200 |
41 | 18 | 200 | 13 | 200 | 21 | 200 | 16 | 200 |
42 | 18 | 200 | 16 | 200 | 23 | 200 | 18 | 200 |
43 | 18 | 200 | 17 | 100 | 24 | 200 | 19 | 200 |
44 | 20 | 200 | 17 | 100 | 23 | 200 | 19 | 200 |
DMF | 18 | 13 | 21 | 16 |
3. Experimental
3.1. General Methods
3.2. General Procedure for the Preparation of Compounds 2–4
3.3. General Procedure for the Preparation of Compounds 5–7
3.4. General Procedure for the Preparation of Compounds 8 and 9
3.5. General Procedure for the Preparation of Compounds 10–12
3.6. General Procedure for the Preparation of Compounds 13–15
3.7. General Procedure for the Preparation of Compounds 16–18
3.8. 4-(4-Bromo-3-aryl-5-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-2-yl)-1H-pyrazol-1-yl)-N-(phenylcarbamothioyl)benzenesulfonamide (19)
3.9. General Procedure for the Preparation of Compounds 20 and 21
3.10. 5H-[1,2,4]Triazino[5,6-b]indole-3-thiol (22)
3.11. 5,10-Dihydro-[1,2,4]triazino[5,6-b]quinoxaline-3-thiol (23)
3.12. 3-Hydrazinyl-5H-[1,2,4]triazino[5,6-b]indole (24)
3.13. 3-Hydrazinyl-5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxaline (25)
3.14. Ethyl [1,2,4]triazolo[3,4-c][1,2,4]triazino[5,6-b]-5H-indole-5-ethanoate (26)
3.15. Ethyl [1,2,4]triazolo[3,4-c][1,2,4]triazino[5,6-b]-5,10-dihydroquinoxaline-5-ethanoate (27)
3.16. [1,2,4]Triazolo[3,4-c][1,2,4]triazino[5,6-b]-5H-indole-5-ethanoic acid hydrazide (28)
3.17. [1,2,4]Triazolo[3,4-c][1,2,4]triazino[5,6-b]-5,10-dihydroquinoxaline-5-ethanoic acid hydrazide (29)
3.18. [1,2,4]Triazolo[3,4-c][1,2,4]triazino[5,6-b]-5H-indole-5-N-(phenylcarbamothioyl) ethanoic acid hydrazide (30)
3.19. [1,2,4]Triazolo[3,4-c][1,2,4]triazino[5,6-b]-5,10-dihydroquinoxaline-5-N-(phenylcarbamothioyl)-ethanoic acid hydrazide (31)
3.20. 1-(5H-[1,2,4]Triazino[5,6-b]indol-3-yl)-3-methyl-1H-pyrazol-5(4H)-one (32)
3.21. 1-(5,10-Dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one (33)
3.22. 1-(5H-[1,2,4]Triazino[5,6-b]indol-3-yl)-3-methyl-4-(propan-2-ylidene)-1H-pyrazol-5(4H)-one (34)
3.23. 1-(5,10-Dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl)-3-methyl-4-(propan-2-ylidene)-1H-pyrazol-5(4H)-one (35)
3.24. 2-((2-(5H-[1,2,4]Triazino[5,6-b]indol-3-yl)hydrazono)methyl)-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one (36)
3.25. 2-((2-(5,10-Dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl)hydrazono)methyl)-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one (37)
3.26. 3-(5H-[1,2,4]Triazino[5,6-b]indol-3-yl)-2-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-2-yl)thiazolidin-4-one (38)
3.27. N'-2-((2-(5,10-Dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl)hydrazono)methyl)-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-ylidene)benzohydrazide (39)
3.28. 3-(6,6-Dimethyl-6,7-dihydro-1H-indol-4(5H)-one)-1,5-dihydro-[1,2,4]triazolo[3,4-c]-5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxaline (40)
3.29. 2-(1-(5H-[1,2,4]Triazino[5,6-b]indol-3-yl)-3-(4-bromophenyl)-1H-pyrazol-5-yl)-(6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one (41)
3.30. General Procedure for the Preparation of Compounds 42–44
3.31. Biological Activity Assay
3.31.1. Inhibition Zone Measurement (IZ)
3.31.2. Minimal inhibitory concentration (MIC)
4. Conclusions
Acknowledgments
Supplementary Materials
References
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Hassan, S.Y. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules 2013, 18, 2683-2711. https://doi.org/10.3390/molecules18032683
Hassan SY. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules. 2013; 18(3):2683-2711. https://doi.org/10.3390/molecules18032683
Chicago/Turabian StyleHassan, Seham Y. 2013. "Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives" Molecules 18, no. 3: 2683-2711. https://doi.org/10.3390/molecules18032683