32434-44-9

Basic information

• Product Name: isofebrifugin
• Synonyms: isofebrifugin;Isofebrifugine;3-[[(3aS,7aS)-Octahydro-2-hydroxyfuro[3,2-b]pyridin-2-yl]methyl]-4(3H)-quinazolinone;alpha-Dichroine;cis-Febrifugine;NSC 290495;ISOFEBRIFUGINE (B604866K055)
• CAS NO: 32434-44-9
• Molecular Formula: C16H19N3O3
• Molecular Weight: 301.3404
• Mol File: 32434-44-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 129-130 °C
• Boiling Point: 519.8°C at 760 mmHg
• Flash Point: 268.2°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 1.24E-11mmHg at 25°C
• Refractive Index: 1.716
• PKA: 12.01±0.20(Predicted)
• CAS DataBase Reference: isofebrifugin(CAS DataBase Reference)
• NIST Chemistry Reference: isofebrifugin(32434-44-9)
• EPA Substance Registry System: isofebrifugin(32434-44-9)

Safety Data

• Hazardous Substances Data: 32434-44-9(Hazardous Substances Data)

Usage

General Description

Isofebrifugin is a chemical compound derived from the Chinese herb Tripterygium wilfordii Hook. f. It is known for its anti-inflammatory and immunosuppressive properties, making it a potential candidate for treating autoimmune diseases and inflammatory conditions. Isofebrifugin has been studied for its ability to inhibit the production of pro-inflammatory cytokines and to modulate the activity of immune cells such as T cells and macrophages. Research has also suggested that isofebrifugin may have potential therapeutic effects in conditions such as rheumatoid arthritis, psoriasis, and other inflammatory disorders. Overall, isofebrifugin shows promise as a natural compound for the development of new treatments for immune-related diseases.

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 
• 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 
• 290315-09-2 (4S,5S)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-4-(2-methoxy-phenylamino)-octan-2-one 
• 290315-13-8 1-((2S,3S)-3-Benzyloxy-piperidin-2-yl)-propan-2-one 
• 223676-06-0 (S)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanal 
• 304436-19-9 benzyl (3aS,7aS)-2-(bromomethyl)-2-methoxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 
• 304436-18-8 benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 
• 304436-17-7 benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate 
• 304436-21-3 benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate 
• 244056-97-1 Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate 
• 391242-48-1 benzyl {2-benzyloxy-5-hydroxy-1-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]-pentyl}carbamate 

Downstream Products

• 24159-07-7 febrifugine 

Relevant articles and documents

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.

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

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.