Halofuginone

Base Information

• Chemical Name: Halofuginone
• CAS No.: 55837-20-2
• Molecular Formula: C₁₆H₁₇BrClN₃O₃
• Molecular Weight: 414.686
• UNII: L31MM1385E,H84E4Y7HC9
• DSSTox Substance ID: DTXSID301339439
• Nikkaji Number: J238.337C
• Wikipedia: Halofuginone
• Wikidata: Q4132745,Q76118383
• NCI Thesaurus Code: C1120
• Metabolomics Workbench ID: 149296
• ChEMBL ID: CHEMBL1199540
• Mol file: 55837-20-2.mol

Synonyms:(+)-halofuginone;(+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone;(+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone monohydrobromide;(-)-halofuginone;(-)-halofuginone hydrobromide;4(3H)-quinazolinone, 7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, hydrochloride (1:1), rel-;4(3H)-quinazolinone, 7-bromo-6-chloro-3-(3-((2S,3R)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, hydrobromide (1:1);4(3H)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, hydrobromide, trans-(+-)-;4(3H)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, trans-, mono(2-hydroxypropanoate)(salt);6-chloro-7-bromo-(+)-febrifugine;6-chloro-7-bromofebrifugine;7-bromo-6-chloro-3,3-(3-hydroxy-2-piperidyl)acetonyl-4(3H)-quinazolinone-hydrolactate;7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone;7-bromo-6-chloro-3-(3-((2S,3R)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone;7-bromo-6-chloro-3-(3-((2S,3R)-3-hydroxy-2-piperidyl)-2-oxo-propyl)quinazolin-4-one hydrobromide;7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone;7-bromo-6-chlorofebrifugine;Cebegine;chloro-bromofebrifugine;chlorobromofebrifugine;Halagon;Halocur;halofuginon;halofuginone;halofuginone HBr;halofuginone HCl;halofuginone hydrobromide;halofuginone hydrobromide, (-)-;halofuginone hydrochloride;halofuginone lactate;halofuginone monohydrobromide;halofuginone monohydrochloride;halofuginone, (+)-;halofuginone, (-)-;halofunginone;RU 19110;RU-19110;RU19110;Stenorol;trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone

Chemical Property of Halofuginone

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >150°C dec.
• Refractive Index: 1.712
• Boiling Point: 595.8 °C at 760 mmHg
• PKA: 14.61±0.40(Predicted)
• Flash Point: 314.1 °C
• PSA: 84.22000
• Density: 1.73 g/cm³
• LogP: 2.21330
• Storage Temp.: -20°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 413.01418
• Heavy Atom Count: 24
• Complexity: 533

Purity/Quality:

97% ^*data from raw suppliers

Halofuginone >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O
• Isomeric SMILES: C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O
• Recent ClinicalTrials: Safety, Tolerability, and Pharmacokinetics of Single and Multiple Doses of HT-100 in Duchenne Muscular Dystrophy
• 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.
• Uses: Halofuginone is a halogenated derivative of febrigugine. It is Used as an antiprotozoal. 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.

Technology Process of Halofuginone

There total 61 articles about Halofuginone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

7-bromo-6-chloro-3-[(4-benzyl-2-hydroxyloctahydrofuran[3,2-b]pyridin-2-yl)methyl]quinazolin-4(3H)-one → 7-bromo-6-chloro-3-[3-(3-hydroxyl-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one (64544-01-0,55837-20-2)

Guidance literature:

With ammonium cerium (IV) nitrate; In ethanol; water; at 20 - 30 ℃;

DOI:10.3390/molecules22071086

Reference yield: 93.0%

(-)-halofuginone didydrobromide (17395-31-2,64924-67-0) → halofuginone (55837-20-2)

Guidance literature:

With potassium carbonate; In water; pH=10;

DOI:10.1016/j.tet.2017.07.041

Reference yield: 80.6%

(+)-isohalofuginone → (+)-halofuginone (55837-20-2)

Guidance literature:

In ethanol; at 18 - 25 ℃;

upstream raw materials:

1-chloro-3-methylbenzene

2-amino-4-bromo-5-chlorobenzoic acid

7-bromo-6-chloro-3,4-dihydroquinazolin-4-one

Downstream raw materials:

halofuginone hydrobromide

halofuginone hydrobromide

(rac)-halofuginone lactate

Refernces

• 1、 Linder, Michael R.,Heckeroth, Anja R.,Najdrowski, Michael,Daugschies, Arwid,Schollmeyer, Dieter,Miculka, Christian. "(2R,3S)-(+)- and (2S,3R)-(-)-Halofuginone lactate: Synthesis, absolute configuration, and activity against Cryptosporidium parvum". . p. 4140 - 4143. Retrieved 2007.
• 2、 -. "Halofuginone with optical activity and synthesis method of intermediate of halofuginone". . . Retrieved 2019/11/28.