32434-44-9

Usage

Uses

Used in Pharmaceutical Industry:
Isofebrifugin is used as an anti-inflammatory and immunosuppressive agent for its ability to mitigate the production of pro-inflammatory cytokines and modulate the activity of immune cells, which is beneficial in treating autoimmune diseases and inflammatory conditions.
Used in Autoimmune Disease Treatment:
Isofebrifugin is utilized as a therapeutic agent for conditions such as rheumatoid arthritis and psoriasis, where its immunosuppressive and anti-inflammatory effects can help manage symptoms and potentially slow disease progression.
Used in Inflammatory Disorder Management:
isofebrifugin serves as a potential treatment option for a range of inflammatory disorders, leveraging its capacity to regulate immune responses and reduce inflammation, thereby improving patient outcomes in various chronic inflammatory conditions.

InChI:InChI=1/C16H19N3O3/c20-15-11-4-1-2-5-12(11)18-10-19(15)9-16(21)8-13-14(22-16)6-3-7-17-13/h1-2,4-5,10,13-14,17,21H,3,6-9H2/t13-,14+,16?/m0/s1

Upstream product

• 223718-11-4 febrifugine 
• 223676-06-0 (S)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanal 
• 491-36-1 4-quinazolinol 
• 491-36-1 4-Hydroxyquinazoline 
• 1046397-98-1 C₂₃H₃₁N₃O₆ 
• 1050609-27-2 (2S,3S)-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]-3-methoxymethoxypiperidine-1-carboxylic acid tert-butyl ester 
• 391243-12-2 cis-(3S)-3-benzyloxy-2-benzyloxycarbonylaminotetrahydropyran 
• 304436-20-2 benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 
• 1061357-71-8 3-benzyloxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 290315-09-2 (4S,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-4-(2-methoxy-phenylamino)-octan-2-one 
• 290315-22-9 (4S,5S)-5-Benzyloxy-8-hydroxy-4-(2-methoxy-phenylamino)-octan-2-one 
• 290315-14-9 tert-butyl (2S,3S)-3-(benzyloxy)-2-(3-bromo-2-oxopropyl)piperidine-1-carboxylate 

Downstream Products

• 24159-07-7 febrifugine 

Relevant academic research and scientific papers

Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone

A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.

Complementary chemoenzymatic routes to both enantiomers of febrifugine

Two complementary strategies for the synthesis of febrifugine are detailed based on previously developed chemoenzymatic approaches to the 3-hydroxypiperidine skeleton. The introduction of the quinazolone-containing side chain in both strategies was based

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

(Chemical Equation Presented) The stereoselective syntheses of 2-substituted and 2,6-disubstituted 3-hydroxypiperidine alkaloids, (+)-isofebrifugine and (-)-sedacryptine, from a common, functionalized nonracemic bicyclic building block are achieved, demon

A convergent total synthesis of (+)-febrifugine

Febrifugine was synthesized in ten steps from N-Boc 4-aminobutan-1-ol by a convergent approach. Georg Thieme Verlag Stuttgart.

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

Ring-opening reactions of semicyclic N,O-acetals possessing an exocyclic nitrogen atom with silicon-based nucleophiles (silyl enol ethers, ketene silyl acetals, allylic silanes, and trimethylsilyl cyanide) were systematically studied for the first time. I

Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction

The antimalarial agents febrifugine (D-1) and isofebrifugine (D-2) were synthesized from chiral 3-piperidinol (D-4), which was asymmetrically prepared by the yeast reduction of 3-piperidone derivatives (DL-3), with dynamic optical resolution.

Asymmetric synthesis of febrifugine and isofebrifugine using yeast reduction

The antimalarial agents febrifugine ((+)-1) and isofebrifugine ((+)-2) were asymmetrically synthesized from chiral piperidin-3-ol ((+)-4), which was prepared by the reductive dynamic optical resolution of the 3-piperidone derivatives ((±)-3) using baker's

Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity

Antimalarial alkaloids febrifugine (1) and isofebrifugine (2) were efficiently synthesized from simple achiral starting materials on the basis of the catalytic asymmetric synthesis. The first key reaction was performed using the tin(II)-mediated catalytic asymmetric aldol protocol to afford chiral aldehyde 3 in high yield with high diastereo- and enantioselectivities. The second key step, a Mannich-type reaction, did not give satisfactory results according to the conventional methods. We then developed a novel aqueous Mannich-type three-component reaction of an aldehyde, an amine, and a vinyl ether using a Lewis acid-surfactant combined catalyst (LASC), and the key intermediates 16 and 17 were obtained in high yields. The final coupling reactions of bromoacetone 14 with 4- hydroxyquinazoline were carried out using basic conditions, and successive deprotection gave 1 and 2, respectively, without any isomerization. These- unambiguous total asymmetric syntheses revealed that the absolute configurations of febrifugine and isofebrifugine were not (2'S,3'R) and (2'R,3'R) as reported previously but (2'R,3'S) and (2'S,3'S), respectively (1' and 2'). Finally, antimalarial activities of the synthesized febrifugine and isofebrifugine, and their antipodes, were examined. It was revealed that the activities and selectivities of natural febrifugine and isofebrifugine were much higher than those of the antipodes.

Catalytic asymmetric synthesis of febrifugine and isofebrifugine

Antimalarial alkaloids, febrifugine (1) and isofebrifugine (2), were synthesized from simple achiral starting materials using tin(II)-catalyzed catalytic asymmetric aldol reaction and lanthanide-catalyzed aqueous three- component reaction as the key steps. These unambigous total syntheses revealed that the absolute configurations of febrifugine and isofebrifugine were not (2'S, 3'R) and (2'R, 3'R) as reported previously but (2'R, 3'S) and (2'S, 3'S), respectively.