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24159-07-7,MFCD01685990
Catalog No.:AA00BE2Y

24159-07-7 | Febrifugine

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1mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE2Y
Chemical Name:
Febrifugine
CAS Number:
24159-07-7
Molecular Formula:
C16H19N3O3
Molecular Weight:
301.3404
MDL Number:
MFCD01685990
SMILES:
O=C(Cn1cnc2c(c1=O)cccc2)CC1NCCCC1O
NSC Number:
315535
Properties
Computed Properties
 
Complexity:
466  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
2  
XLogP3:
0.1  

Downstream Synthesis Route

[1]Katoh,Miho;Matsune,Ryuichiro;Honda,Toshio[Heterocycles,2006,vol.67,#1,p.189-204]

[2]Katoh,Miho;Matsune,Ryuichiro;Nagase,Hiromasa;Honda,Toshio[TetrahedronLetters,2004,vol.45,#33,p.6221-6223]

[1]Okitsu;Suzuki;Kobayashi[JournalofOrganicChemistry,2001,vol.66,#3,p.809-823]

Literature

Title: Febrifugine analogue compounds: synthesis and antimalarial evaluation.

Journal: Bioorganic & medicinal chemistry 20120115

Title: Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone.

Journal: The Journal of organic chemistry 20100115

Title: A new reaction motif: 'homo-S(N)2'-like' direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.

Journal: Journal of the American Chemical Society 20090909

Title: Complementary chemoenzymatic routes to both enantiomers of febrifugine.

Journal: Organic & biomolecular chemistry 20090721

Title: Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.

Journal: Bioorganic & medicinal chemistry 20090701

Title: Synthesis and comparison of antimalarial activity of febrifugine derivatives including halofuginone.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20090501

Title: Effects of limonoids from Cipadessa fruticosa on fall armyworm.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20090101

Title: Possible involvement of IFN-gamma in early mortality of Plasmodium berghei NK65-infected BALB/c mice after febrifugine treatment.

Journal: The Southeast Asian journal of tropical medicine and public health 20081101

Title: Asymmetric synthesis of (+)-isofebrifugine and (-)-sedacryptine from a common chiral nonracemic building block.

Journal: Organic letters 20080904

Title: Differentiation of the diastereomeric synthetic precursors of isofebrifugine and febrifugine by electrospray ionization tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20080701

Title: Febrifugine derivative antimalarial activity: quantum mechanical predictors.

Journal: Revista do Instituto de Medicina Tropical de Sao Paulo 20080101

Title: Exploration of a new type of antimalarial compounds based on febrifugine.

Journal: Journal of medicinal chemistry 20060727

Title: Synthesis and evaluation of febrifugine analogues as potential antimalarial agents.

Journal: Bioorganic & medicinal chemistry letters 20060401

Title: Antimalarials: shortages and searches.

Journal: Molecular interventions 20051001

Title: Concise synthesis of dl-febrifugine.

Journal: Chemical & pharmaceutical bulletin 20050701

Title: Cytokine and antibody production during the course of resolution in Plasmodium yoelii 17XL-infected BALB/c mice treated with febrifugine and isofebrifugine mixture from leaves of Hydrangea macrophylla var. Otaksa.

Journal: Parasitology research 20041001

Title: Combination effects of chloroquine with the febrifugine and isofebrifugine mixture against a blood-induced infection with chloroquine-resistant Plasmodium berghei NK65 in ICR mice.

Journal: Phytotherapy research : PTR 20031201

Title: Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.

Journal: Journal of medicinal chemistry 20030925

Title: Different responses of three rodent Plasmodia species, Plasmodium yoelii 17XL, P. berghei NK65 and P. chabaudi AS on treatment with febrifugine and isofebrifugine mixture from Hydrangea macrophylla var. Otaksa leaf in ICR mice.

Journal: Phytotherapy research : PTR 20030601

Title: Re-revision of the stereo structure of piperidine lactone, an intermediate in the synthesis of febrifugine.

Journal: Chemical & pharmaceutical bulletin 20020701

Title: Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.

Journal: Journal of medicinal chemistry 20020606

Title: Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals possessing an exocyclic nitrogen atom: mechanistic aspect and application to piperidine alkaloid synthesis.

Journal: Journal of the American Chemical Society 20011219

Title: Synthesis and antimalarial activity of febrifugine derivatives.

Journal: Chemical & pharmaceutical bulletin 20010601

Title: A concise enantioselective synthesis of antimalarial febrifugine alkaloids.

Journal: Organic letters 20010322

Title: Herman JD, et al. The cytoplasmic prolyl-tRNA synthetase of the malaria parasite is a dual-stage target of febrifugine and its analogs. Sci Transl Med. 2015 May 20;7(288):288ra77.

Title: McLaughlin NP, et al. The chemistry and biology of febrifugine and halofuginone. Bioorg Med Chem. 2014 Apr 1;22(7):1993-2004.

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