Stenorol

Base Information

• Chemical Name: Stenorol
• CAS No.: 64924-67-0
• Molecular Formula: BrH*C₁₆H₁₇BrClN₃O₃
• Molecular Weight: 495.598
• European Community (EC) Number: 694-602-6
• NSC Number: 713205
• UNII: Q86XE47UJ3
• NCI Thesaurus Code: C2656
• ChEMBL ID: CHEMBL1969752
• Mol file: 64924-67-0.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 Stenorol

Chemical Property:

• Vapor Pressure: 4.84E-15mmHg at 25°C
• Melting Point: 247° (dec)
• Boiling Point: 595.8 °C at 760 mmHg
• Flash Point: 314.1 °C
• PSA: 84.22000
• LogP: 3.17140
• Storage Temp.: Store at -20°C
• Solubility.: Soluble to 100 mM in DMSO.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 494.93829
• Heavy Atom Count: 25
• Complexity: 533

Purity/Quality:

99%min ^*data from raw suppliers

Halofuginone hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O.Br
• Isomeric SMILES: C1C[C@H]([C@@H](NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O.Br
• Recent ClinicalTrials: Halofuginone Hydrobromide in Treating Patients With HIV-Related Kaposi's Sarcoma
• Uses: Halogenated derivative of Febrifugine. Halofuginone hydrobromide is used as an antiprotozoal (coccidiostat).

Technology Process of Stenorol

There total 79 articles about Stenorol 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: 99.0%

7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone (55837-20-2) → halofuginone hydrobromide (17395-31-2,64924-67-0)

Guidance literature:

With hydrogen bromide; at 20 ℃; for 2h;

Reference yield: 93.8%

C16H17BrClN3O3*HBr → halofuginone hydrobromide (17395-31-2,64924-67-0)

Guidance literature:

In water; isopropyl alcohol; at 80 - 82 ℃; Solvent; Temperature;

Reference yield: 60.0%

(-)-(2R,3S)-benzyl 2-(3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)-2-oxopropyl)-3-hydroxypiperidine-1-carboxylate → (+)-halofuginone didydrobromide (17395-31-2,64924-67-0)

Guidance literature:

With hydrogen bromide; acetic acid; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2017.07.041

upstream raw materials:

1-chloro-3-methylbenzene

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

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

7-bromo-6-chloro-3-[3-(3-hydroxyl-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one

Refernces

• 1、 Perali, Ramu Sridhar,Bandi, Anjaneyulu. "Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone". . . Retrieved 2020/07/04.
• 2、 -. "Synthetic method for halofuginone and intermediate of halofuginone". . . Retrieved 2019/11/28.