55837-20-2 Usage
Description
Halofuginone hydrobromide (Halofuginone) is a specific collagen Type I inhibitor that antagonize or inhibit the development of new blood vessels, hence can prevent intimal hyperplasia at a vascular anastomosis. It is used in the treatment or prevention of coccidiosis in both humans and animals.
Chemical Properties
Off-White Solid
Uses
Different sources of media describe the Uses of 55837-20-2 differently. You can refer to the following data:
1. Halofuginone is a halogenated derivative of febrigugine. It is Used as an antiprotozoal.
2. Halofuginone is a coccidiostat for young chickens and young turkeys. In higher doses, halofuginone is a growth depressant, impairs feed utilization, and reduces feed intake. In rats it causes alopecia. The compound is prohibited from use during the last four days before slaughter (withdrawal period).Halofuginone is extracted from enzyme-digested chicken liver as a free base into ethyl acetate and partitioned into ammonium acetate buffer solution. The halofuginone is concentrated with Sep-Pak C18 cartridges and eluted with methyl alcohol. The eluant is evaporated to dryness and the residue dissolved in the HPLC mobile phase. Analysis is achieved by HPLC using a BONDAPAK C18 column and a variable wavelength UV detector.
Brand name
Stenorol(Roussel-UCLAF, France).
Biological Activity
Halofuginone is a halogenated derivative of febrifugine, a natural quinazolinone-containing compound found in the Chinese herb D. febrifuga. It has antimalarial and anticoccidial actions. In mammals, halofuginone at 10 ng/ml down-regulates Smad3, blocking TGF-β signaling and preventing both the differentiation of fibroblasts to myofibroblasts and the transitioning of epithelial cells to mesenchymal cells. Through this action, halofuginone blocks fibrosis and tumor progression in a variety of different models. This compound also competitively inhibits prolyl-tRNA synthetase (Ki = 18.3 nM), activating the amino acid starvation response. This prevents the differentiation of TH17 cells, blunting an autoimmune response.
Synthesis
A scalable total synthesis of halofuginone has been accomplished. This synthetic route features a total of 12 steps of highly efficient reactions, without any chromatographic purification. Halofuginone was obtained in 17% overall yield and over 98.5% HPLC purity. All the reaction conditions are mild and reliable. In addition, no hazardous materials are used or produced. All reagents are commercially available and inexpensive. This route is safe, robust, scalable, cost-effective, and environmentally benign.A Scalable Total Synthesis of Halofuginone
Mode of action
Halofuginone is an analog of febrifugine-an alkaloid originally isolated from the plant Dichroa febrifuga. During recent years, halofuginone has attracted much attention because of its wide range of beneficial biological activities, which encompass malaria, cancer, and fibrosis-related and autoimmune diseases. At present two modes of halofuginone actions have been described: (1) Inhibition of Smad3 phosphorylation downstream of the TGFβ signaling pathway results in inhibition of fibroblasts-to-myofibroblasts transition and fibrosis. (2) Inhibition of prolyl-tRNA synthetase (ProRS) activity in the blood stage of malaria and inhibition of Th17 cell differentiation thereby inhibiting inflammation and the autoimmune reaction by activation of the amino acid starvation and integrated stress responses.
Check Digit Verification of cas no
The CAS Registry Mumber 55837-20-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,5,8,3 and 7 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 55837-20:
(7*5)+(6*5)+(5*8)+(4*3)+(3*7)+(2*2)+(1*0)=142
142 % 10 = 2
So 55837-20-2 is a valid CAS Registry Number.
InChI:InChI=1/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m1/s1
55837-20-2Relevant articles and documents
A Scalable Total Synthesis of Halofuginone
Xu, Hua,Yin, Wenhao,Liang, Haoqiang,Nan, Yanbo,Qiu, Fayang,Jin, Yehua
, p. 990 - 997 (2019)
A scalable total synthesis of halofuginone has been accomplished. This synthetic route features a total of 12 steps of highly efficient reactions, without any chromatographic purification. Halofuginone was obtained in 17% overall yield and over 98.5% HPLC purity. All the reaction conditions are mild and reliable. In addition, no hazardous materials are used or produced. All reagents are commercially available and inexpensive. This route is safe, robust, scalable, cost-effective, and environmentally benign.
New synthesis process for preparing veterinary bulk drug halofuginone hydrobromide
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Paragraph 0021-0026, (2021/10/20)
The invention discloses a process method for preparing veterinary raw material drug halofuginone hydrobromide, and relates to the field of veterinary drugs and the technical field of drug synthesis. According to the invention, a novel process route is adopted, 7-bromo-3-(8-bromo-5-hydroxy-2-oxo-3-octenyl)-6-chloro-4 (3H)-quinazolinone is taken as a starting raw material, and the halofuginone hydrobromide is prepared through three-step reaction of ammonolysis, purification and salification, so that the problems of difficulty in obtaining raw materials, harsh reaction conditions, high cost and the like in the existing synthesis method are solved. The novel synthesis process for preparing the veterinary drug halofuginone hydrobromide is simple in process operation, low in production cost, few in steps, high in total yield, small in pollution and suitable for industrial mass production.
Synthetic method for halofuginone and intermediate of halofuginone
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, (2019/11/28)
The invention relates to a synthetic method for halofuginone and an intermediate of the halofuginone. The reaction formula is shown in the description, wherein R1 is one selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and t-butyl; R2 is one selected from the group consisting of methyl and ethyl; and R3 is one selected from the group consisting of methoxyformyl, ethoxyformyl, tert-butoxyformyl, benzyloxyformyl, trichloroethoxyformyl and benzyl. The synthetic method provided by the invention has the advantages of a simple process, low costs, few by-products in the synthetic process, a simple purification process, no need of column chromatography purification, a high product yield, less impurities, high purity, and controllable product quality, easily meets ICH declaration requirements and can be used for industrial production of the halofuginone.
