A Novel Synthesis of the Efficient Anti-Coccidial Drug Halofuginone Hydrobromide
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Halofuginone Hydrobromide
2.2. Evaluation on Antioccidial Activity of Halofuginone Hydrobromide (Hh) in Chickens
3. Experimental Section
3.1. General Information
3.2. Synthesis
3.2.1. Synthesis of 7-bromo-6-choroquinazolin-4(3H)-one (2)
3.2.2. 7-Bromo-6-chloro-3-(2-chloropropenyl)quinazolin-4(3H)-one (3)
3.2.3. 7-Bromo-6-chloro-3-(3-chloroacetonyl)quinazalin-4(3H)-one (4)
3.2.4. 7-Bromo-6-chloro-3-(8-bromo-5-hydroxyl-2-oxo-3-octenyl) quinazolin-4(3H)-one (5)
3.2.5. 7-Bromo-6-chloro-3-[(4-benzyl-2-hydroxyl-octahydrofuran[3,2-b]pyridine-2)methyl]quinazol-in-4(3H)-one (6)
3.2.6. 7-Bromo-6-chloro-3-[3-(3-hydroxyl-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one (7)
3.2.7. (±)-trans-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)acetonyl]quinazolin-4(3H)-one hydro-bromide (halofuginone hydrobromide, 1)
3.3. Evaluation on the Antioccidial Activity of Halofuginone Hydrobromide in Chickens
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Catalyst [a] | Result | Solvent [b] | Result |
---|---|---|---|
Sodium methoxide | Incomplete reaction | Ethanol | Favorable reaction |
Sodium ethoxide | Incomplete reaction | Isopropanol | Favorable reaction |
Potassium tert-butoxide | Favorable reaction | tert-Butanol | Favorable reaction |
Sodium hydride | More by-products | N,N-dimethylformamide | Favorable reaction, but complicated work-up |
N-butyl lithium | More by-products | Ether | Slow reaction |
/ | / | Tetrahydrofuran | More by-products |
Group [#] | RBWGR [a] (%) | SR [b] (%) | ALS [c] | OS [d] | ACI [e] |
---|---|---|---|---|---|
I | 100 | 100 | 0 | 0 | 200.00 |
II | 46.02 | 40 | 32 | 20 | 34.02 |
III | 99.68 | 100 | 0 | 1 | 198.68 |
IV | 106.54 | 100 | 2 | 1 | 203.54 |
V | 93.02 | 100 | 11 | 5 | 177.02 |
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Zhang, J.; Yao, Q.; Liu, Z. A Novel Synthesis of the Efficient Anti-Coccidial Drug Halofuginone Hydrobromide. Molecules 2017, 22, 1086. https://doi.org/10.3390/molecules22071086
Zhang J, Yao Q, Liu Z. A Novel Synthesis of the Efficient Anti-Coccidial Drug Halofuginone Hydrobromide. Molecules. 2017; 22(7):1086. https://doi.org/10.3390/molecules22071086
Chicago/Turabian StyleZhang, Junren, Qizheng Yao, and Zuliang Liu. 2017. "A Novel Synthesis of the Efficient Anti-Coccidial Drug Halofuginone Hydrobromide" Molecules 22, no. 7: 1086. https://doi.org/10.3390/molecules22071086