24159-07-7

Basic information

• Product Name: Febrifugine
• Synonyms: Febrifugine;β-dichroine;Febrifugine，Isofebrifugine;3-[3-[(2R,3S)-3-Hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone;BETA-Febrifugine;3-(3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one;febrifugin
• CAS NO: 24159-07-7
• Molecular Formula: C16H19N3O3
• Molecular Weight: 301.344
• Mol File: 24159-07-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 139-140°; mp 154-156°
• Boiling Point: 508.2 °C at 760 mmHg
• Flash Point: 261.1 °C
• Appearance: /
• Density: 1.39
• Vapor Pressure: 3.76E-11mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: 2-8°C
• PKA: 14.61±0.40(Predicted)
• CAS DataBase Reference: Febrifugine(CAS DataBase Reference)
• NIST Chemistry Reference: Febrifugine(24159-07-7)
• EPA Substance Registry System: Febrifugine(24159-07-7)

Safety Data

• Hazardous Substances Data: 24159-07-7(Hazardous Substances Data)

Usage

Description

Febrifugine is a quinazolinone alkaloid originally isolated from D. febrifuga that has antimalarial activity. It reduces parasitemia and decreases mortality in mice infected with the P. berghei strain NK65 when administered at a dose of 1 mg/kg per day beginning prior to or on the day of infection.

Uses

Febrifugine is a quinazoline alkaloid with significant antimalarial and anticancerous efficacy. Febrifugine is an NRF2 inhibitor, that works with halofuginone for the treatment of chemo- and radio-resistant forms of cancer. Febrifugine analogs also functions as antimalarial, anticancer agents and in the prevention of chicken coccidiosis.

InChI:InChI=1/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2

Upstream product

• 109813-59-4 3-{3-[(2RS,3SR)-1-ethoxycarbonyl-3-methoxy-2-piperidinyl]-2-oxopropyl}-4(3H)-quinazolinone 
• 473436-50-9 benzyl 2,3-dihydroxy-1-piperidinecarboxylate 
• 683219-88-7 3-amino-3-tetrahydro[2]furyl-propionic acid 
• 223676-06-0 (S)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanal 
• 491-36-1 4-quinazolinol 
• 330798-19-1 [(S)-4-Hydroxy-4-(methoxy-methyl-carbamoyl)-butyl]-carbamic acid benzyl ester 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 866488-35-9 (E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate 
• 1174147-50-2 C₂₂H₃₅NO₄Si 
• 1174147-57-9 C₃₀H₃₉N₃O₅Si 

Relevant articles and documents

Chiral synthesis of (+)-febrifugine and (-)-isofebrifugine by means of samarium diiodide-promoted carbon-nitrogen bond cleavage reaction

(+)-Febrifugine, a potential anti-malarial piperidine alkaloid, was synthesized from (4S)-hydroxyproline methyl ester, stereoselectively, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was involved as a key reaction. A stereocon

Stereocontrolled synthesis of a potent antimalarial alkaloid, (+)-febrifugine

A novel and stereocontrolled synthetic path to a potential antimalarial piperidine alkaloid, (+)-febrifugine, was established by employing a reductive deamination of a proline derivative with samarium diiodide, as a key step. A novel and stereocontrolled

An asymmetric synthesis of febrifugine, halofuginone and their hemiketal isomers

A new synthesis of both enantiomers of naturally occurring febrifugine (1) and its analogue halofuginone (3) are reported. This robust route relies on an enzymatic kinetic resolution (EKR)-cross metathesis (CM) sequence, performed on allylic alcohol 8. A diastereoselective Lewis acid-mediated cyclisation of resultant enone 6 affords piperidine 12. In relation to its enantiomeric excess, values of 87 and 88% e.e were obtained for both enantiomers of 12 and for (?)-12 this was increased to 98% e.e by conducting the resolution process twice. A bromination (featuring an in situ temporary alcohol protection), alkylation and amino-deprotection sequence finally afforded the target compounds (+)- and (?)-1, and (+)- and (?)-3. Studies demonstrate that, as their ammonium salts, the compounds are stereochemically stable. However, as their free-bases, particularly in chloroform, C-2 isomerisation occurs. This isomerisation has been taken advantage of synthetically to provide enantioenriched (+)-isofebrifugine (2) and both enantiomers of isohalofuginone (14).

METHOD FOR PREPARING HALOFUGINONE DERIVATIVE

A method for preparing a halofuginone derivative, in particular a method for preparing an inhibitor medicament expressed by specific I-type procollagen in the invention a condensate of formula (II) reacts for 12-35 hours in a catalytic hydrogenation solvent with the existence of Ni—B amorphous alloy catalyst, at the hydrogen pressure of 0.1-10 Mpa and at the temperature of 10-60° C., and then the catalyst is filtered, the filtrate is decompressed to recover the solvent, the pH value is regulated to obtain a crude product of formula (I), and the crude product of the formula (I) is refined to obtain a refined product of formula (I).