Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biology
2.2.1. Antibacterial Activities
Compound No. | Gram-Negative | Gram-Positive | ||
---|---|---|---|---|
E. coli | P. aeruginosa | S. aureus | B. megaterium | |
4 | 15 | 13 | 16 | 18 |
5 | 17 | 14 | 19 | 20 |
9 | 13 | 12 | 14 | 15 |
12 | 12 | 11 | 13 | 14 |
14 | 14 | 13 | 15 | 16 |
15 | 12 | 11 | 14 | 14 |
20 | 13 | 11 | 14 | 16 |
21 | 12 | 12 | 13 | 15 |
24 | 18 | 16 | 18 | 21 |
26a | 13 | 12 | 13 | 15 |
26b | 12 | 14 | 12 | 16 |
26c | 13 | 14 | 12 | 17 |
26d | 12 | 11 | 13 | 14 |
26e | 13 | 12 | 14 | 13 |
26f | 14 | 13 | 15 | 17 |
26g | 9 | 11 | 11 | 10 |
26h | 21 | 20 | 20 | 21 |
Tetracycline | 20 | 18 | 22 | 24 |
2.2.2. Minimum Inhibitory Concentrations
Compound No. | Gram-Negative | Gram-Positive | ||
---|---|---|---|---|
E. coli | P. aeruginosa | S. aureus | B. megaterium | |
4 | 25 | 30 | 30 | 35 |
5 | 15 | 15 | 20 | 20 |
9 | 35 | 40 | 35 | 45 |
12 | 40 | 45 | 50 | 50 |
14 | 20 | 30 | 35 | 35 |
15 | 45 | 40 | 45 | 50 |
20 | 40 | 45 | 50 | 40 |
21 | 35 | 40 | 50 | 45 |
24 | 15 | 20 | 20 | 20 |
26a | 30 | 35 | 35 | 35 |
26b | 30 | 30 | 35 | 35 |
26c | 25 | 35 | 40 | 35 |
26d | 40 | 45 | 45 | 55 |
26e | 45 | 45 | 55 | 50 |
26f | 35 | 40 | 40 | 35 |
26g | 55 | 50 | 70 | 50 |
26h | 15 | 20 | 20 | 20 |
Tetracycline | 10 | 15 | 15 | 15 |
2.2.3. DNA Cleavage Assay
2.2.4. Superoxide Dismutase Mimetic Catalytic Activity
Compound No. | Δ through 4 min | % Inhibition |
---|---|---|
Control | 0.548 | — |
Horseradish peroxidase | 0.169 | 69.2 |
4 | 0.297 | 45.8 |
5 | 0.264 | 51.8 |
9 | 0.326 | 40.5 |
12 | 0.364 | 33.6 |
14 | 0.272 | 50.4 |
15 | 0.381 | 30.5 |
20 | 0.332 | 39.4 |
21 | 0.337 | 38.5 |
24 | 0.273 | 50.2 |
26a | 0.305 | 44.3 |
26b | 0.314 | 42.7 |
26c | 0.308 | 43.8 |
26d | 0.382 | 30.3 |
26e | 0.358 | 34.7 |
26f | 0.294 | 46.4 |
26g | 0.386 | 29.6 |
26h | 0.256 | 53.3 |
2.2.5. DPPH Free Radical Scavenging Activity
2.2.6. ABTS Radical Cation Decolorization Assay
2.2.7. Nitric Oxide (NO) Scavenging Assay
3. Experimental Section
3.1. General Information
3.1.1. Synthesis of 2-Hydroxy-N-phenylbenzohydrazonoyl Bromide (4)
3.1.2. Synthesis of 2-(5-(2-Hydroxyphenyl)-2,4-diphenyl-2H-1,2,4-triazol-3(4H)-ylidene)malononitrile (9) and 2-(3-(2-Naphthoyl-1,4-diphenyl-1H-1,2,4-triazol-5(4H)-ylidene)malononitrile (10)
3.1.3. General Procedure for the Preparation of Bis([1,2,4]triazolo[4,3-a]pyrimidine) Derivatives 12,13), Bis([1,2,4]triazolo[4,5-a]benzimidazole) Derivative 14 and 3-(2-Hydroxyphenyl)-8-methyl-1-phenyl-1H-pyrimido[1,2-b][1,2,4,5]tetrazine-6-(4H)-one (15)
3.1.4. Synthesis of 2-(4,5-Dihydro-5-imino-4-phenyl-1,3,4-thiadiazol-2-yl)phenol (20)
3.1.5. Synthesis of 1-(2-Hydroxyphenyl-3-phenyl-1,3,4-thiadiazol-4,(3H)-ylidene)hydrazine (21) and 4,5-Dihydro-4-phenyl-5-(phenylimino)-1,3,4-thiadiazol-2-yl)phenol (24)
3.2. Biology
3.2.1. Antibacterial Activities
3.2.2. Minimum Inhibitory Concentrations (MIC)
3.2.3. DNA Cleavage Assay
3.2.4. Superoxide Dismutase (SOD) Mimetic Catalytic Activity Assay
3.2.5. 2,2,-Diphenyl-1-Picrylhydrazyl (DPPH) Free Radical Scavenging Activity Assay
3.2.6. 2,2'-Azino-bis-3-ethylbenzthiazoline-6-sulphonic Acid (ABTS) Radical Cation Assay
3.2.7. Nitric Oxide (NO) Scavenging Assay
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Al-Omair, M.A.; Sayed, A.R.; Youssef, M.M. Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities. Molecules 2015, 20, 2591-2610. https://doi.org/10.3390/molecules20022591
Al-Omair MA, Sayed AR, Youssef MM. Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities. Molecules. 2015; 20(2):2591-2610. https://doi.org/10.3390/molecules20022591
Chicago/Turabian StyleAl-Omair, Mohammed A., Abdelwahed R. Sayed, and Magdy M. Youssef. 2015. "Synthesis of Novel Triazoles, Tetrazine, Thiadiazoles and Their Biological Activities" Molecules 20, no. 2: 2591-2610. https://doi.org/10.3390/molecules20022591