Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin- 4-one Derivatives
Abstract
:Introduction
Results and Discussion
Entry a | Reaction time / h | KOH concentration / % (w/w) | The amount of Bu4NBr / mol % | Reaction temperature / °C | Yield b / % |
1 | 1 | 30 | 3 | 88-90 | 38.8 |
2 | 1 | 30 | 5 | 88-90 | 62.2 |
3 | 1 | 30 | 8 | 88-90 | 77.1 |
4 | 1 | 30 | 10 | 88-90 | 77.4 |
5 | 1 | 30 | 0 | 88-90 | 8.5 |
6 | 1 | 10 | 8 | 88-90 | 48.5 |
7 | 1 | 20 | 8 | 88-90 | 69.1 |
8 | 1 | 35 | 8 | 88-90 | 83.0 |
9 | 1 | 40 | 8 | 88-90 | 74.0 |
10 | 1 | 35 | 8 | 20-25 | 4.3 |
11 | 1 | 35 | 8 | 40-45 | 13.3 |
12 | 1 | 35 | 8 | 60-65 | 65.0 |
13 | 2 | 35 | 8 | 88-90 | 83.8 |
14 | 0.75 | 35 | 8 | 88-90 | 74.5 |
15 | 0. 5 | 35 | 8 | 88-90 | 55.9 |
Entry a | Reaction time / h | organic phase | The amount of solvent / mL | Yield b / % |
1 | 1 | CHCl3 | 10 | 25.5 |
2 | 1 | C6H6 | 10 | 45.2 |
3 | 1 | CH3COOEt | 10 | 54.3 |
4 | 1 | Toluene | 10 | 83.0 |
Compd | 3a | 3b | 3c | 3d | 3e | 3f |
X- | H | F | Cl | Br | H | F |
R- | Et | Et | Et | Et | n-Pr | n-Pr |
bYields /% | 79.5 | 74.5 | 74.5 | 77.0 | 83.0 | 92.2 |
Compd | 3g | 3h | 3i | 3j | 3k | 3l |
X- | Cl | Br | H | F | Cl | Br |
R- | n-Pr | n-Pr | allyl | allyl | allyl | allyl |
bYields /% | 83.1 | 87.0 | 70.0 | 72.7 | 82.5 | 70.9 |
Antifungal activity bioassay
Compd (50 μg/mL) | Fusarium oxysporum | Gibberella zeae | Valsa mali |
3a | 17.9 | 17.6 | 8.7 |
3b | 14.2 | 11.8 | 6.5 |
3c | 37.5 | 55.0 | 24.4 |
3d | 33.3 | 35.4 | 21.7 |
3e | 21.2 | 17.3 | 16.9 |
3f | 4.9 | 17.0 | 14.5 |
3g | 20.4 | 5.5 | 15.9 |
3h | 47.2 | 50.3 | 40.9 |
3i | 15.3 | 19.9 | 0.9 |
3j | 13.9 | 26.7 | 13.4 |
3k | 36.4 | 49.1 | 28.3 |
3l | 32.4 | 37.0 | 30.4 |
Hymexazol | 55.4 | 50.4 | 22.5 |
Conclusions
Experimental
General
Preparation of 3-Alkylquinazolin-4-one Derivatives 3a-3l
Bioassays
Acknowledgements
References
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Ouyang, G.; Zhang, P.; Xu, G.; Song, B.; Yang, S.; Jin, L.; Xue, W.; Hu, D.; Lu, P.; Chen, Z. Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin- 4-one Derivatives. Molecules 2006, 11, 383-392. https://doi.org/10.3390/11060383
Ouyang G, Zhang P, Xu G, Song B, Yang S, Jin L, Xue W, Hu D, Lu P, Chen Z. Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin- 4-one Derivatives. Molecules. 2006; 11(6):383-392. https://doi.org/10.3390/11060383
Chicago/Turabian StyleOuyang, Guiping, Peiquan Zhang, Gangfang Xu, Baoan Song, Song Yang, Linhong Jin, Wei Xue, Deyu Hu, Ping Lu, and Zhuo Chen. 2006. "Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin- 4-one Derivatives" Molecules 11, no. 6: 383-392. https://doi.org/10.3390/11060383