(+)-Isofebrifugine

Base Information

• Chemical Name: (+)-Isofebrifugine
• CAS No.: 24159-07-7
• Molecular Formula: C₁₆H₁₉N₃O₃
• Molecular Weight: 301.345
• Hs Code.: 2933990090
• European Community (EC) Number: 683-166-2
• Nikkaji Number: J1.445.080G
• Wikipedia: Febrifugine
• Wikidata: Q104250952
• Metabolomics Workbench ID: 131459
• ChEMBL ID: CHEMBL3348937
• Mol file: 24159-07-7.mol

Synonyms:febrifugine;isofebrifugine

Chemical Property of (+)-Isofebrifugine

Chemical Property:

• Vapor Pressure: 3.76E-11mmHg at 25°C
• Melting Point: 139-140°; mp 154-156°
• Boiling Point: 508.2 °C at 760 mmHg
• PKA: 14.61±0.40(Predicted)
• Flash Point: 261.1 °C
• PSA: 84.22000
• Density: 1.39 g/cm³
• LogP: 0.79740
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 301.14264148
• Heavy Atom Count: 22
• Complexity: 466

Purity/Quality:

Febrifugine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
• Isomeric SMILES: C1C[C@@H]([C@@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
• 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.

Technology Process of (+)-Isofebrifugine

There total 126 articles about (+)-Isofebrifugine 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: 97.0%

(-)-(2R,3S)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate → febrifugine (24159-07-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2017.07.041

Reference yield: 93.0%

(2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (304665-11-0) → febrifugine (24159-07-7)

Guidance literature:

With hydrogenchloride; In water; Heating;

DOI:10.1021/ol006384f

Reference yield: 92.0%

(2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (304665-12-1) → febrifugine (24159-07-7)

Guidance literature:

With hydrogenchloride; for 26h; Heating;

DOI:10.3987/COM-05-S(T)12

upstream raw materials:

3-{3-[(2RS,3SR)-1-ethoxycarbonyl-3-methoxy-2-piperidinyl]-2-oxopropyl}-4(3H)-quinazolinone

(E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine

benzyl 2,3-dihydroxy-1-piperidinecarboxylate

Refernces

• 1、 Takeuchi, Yasuo,Abe, Hitoshi,Harayama, Takashi. "Total synthesis of dl-febrifugine and dl-isofebrifugine". . p. 905 - 906. Retrieved 1999.
• 2、 Wang, Chen,Mao, Zhuo-Ya,Liu, Yi-Wen,Wang, Qiao-E,Si, Chang-Mei,Wei, Bang-Guo,Lin, Guo-Qiang. "Stereoselective Intermolecular [4+2] Process of N,O-acetals with Terminal Alkynes for Construction of Functional cis-Pyrido and Pyrrolo[1,2-c][1,3]oxazin-1-ones". . p. 822 - 831. Retrieved 2020/01/03.
• 3、 Pansare, Sunil V.,Paul, Eldho K.. "Synthesis of (+)-febrifugine and a formal synthesis of (+)-halofuginone employing an organocatalytic direct vinylogous aldol reaction". . p. 1863 - 1869. Retrieved 2013/07/26.