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Molecules 2017, 22(7), 1086; doi:10.3390/molecules22071086

A Novel Synthesis of the Efficient Anti-Coccidial Drug Halofuginone Hydrobromide

1,2,†
,
3,†
and
1,*
1
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
2
Laboratory of Veterinary Pharmacology and Toxicology, College of Veterinary Medicine, Nanjing Agricultural University, Nanjing 210095, China
3
School of Pharmacy, China Pharmaceutical University, Nanjing 210009, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 9 June 2017 / Revised: 28 June 2017 / Accepted: 28 June 2017 / Published: 30 June 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Background: Halofuginone hydrobromide (1) is recognized as an effective drug against several species of Eimeria (E.) in poultry. In this paper, we describe a convenient and low cost preparation method for the compound, as well as primary validation of its activity. Methods: First, 7-bromo-6-chloroquinazolin-4(3H)-one (2) was prepared from m-chlorotoluene by a conventional process, and then chloroacetone was creatively introduced in two steps. Finally, halofuginone hydrobromide (1) was obtained from 7-bromo-6-chloro-3-(3-cholroacetonyl) quinazolin-4(3H)-one (4) by a four-step reaction sequence including condensation, cyclization, deprotection and isomerization. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS and 1H-NMR. Besides, the protective effect of compound 1-supplemented chicken diet at doses of 6, 3 and 1.5 mg per 1 kg were evaluated on chickens infected with E. tenella, by reduction in mortality, weight loss, fecal oocyst excretion and gut pathology, respectively. Results: Halofuginone hydrobromide (1) was prepared successfully by and improved and innovative method based on traditional research. Moreover, the synthesized halofuginone hydrobromide significantly exhibited an anti-coccidial property. Conclusions: The fruitful work described in this Communication has resulted in halofuginone hydrobromide, which has a good pharmaceutical development prospects, becoming more available for large-scale production. View Full-Text
Keywords: febrifugine; halofuginone hydrobromide; asymmetric synthesis; 4(3H)-quinazolinone; piperidine febrifugine; halofuginone hydrobromide; asymmetric synthesis; 4(3H)-quinazolinone; piperidine
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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.

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