26454-83-1

Usage

Structural Features

Contains a furan ring
2-amino group attached to the furan ring
4-methoxyphenyl group attached to the furan ring
Carbonitrile functional group at the 3-position

Potential Applications

Medicinal chemistry and drug development
Synthesis of other organic compounds and materials

Pharmacological Properties

Potential pharmacological properties yet to be fully elucidated

Research Needs

Further research and experimentation required to fully understand and harness its potential uses and properties.

InChI:InChI=1/C12H10N2O2/c1-15-10-4-2-8(3-5-10)11-6-9(7-13)12(14)16-11/h2-6H,14H2,1H3

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 26454-79-5 2-(2-(4-methoxyphenyl)-2-oxoethyl)malononitrile 
• 25939-02-0 4-fluoro-N'-phenylbenzohydrazonoyl chloride 
• 36590-52-0 N-phenyl-p-chlorobenzohydrazonoyl chloride 
• 25939-01-9 p-toluoyl chloride phenylhydrazone 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 109-77-3 malononitrile 

Downstream Products

• 453590-24-4 6-(4-methoxy-phenyl)-furo[2,3-d]pyrimidin-4-ylamine 
• 453590-06-2 N-[3-cyano-5-(4-methoxyphenyl)-2-furanyl]benzamide 

Relevant academic research and scientific papers

Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors

Novel furan 6a-c, furo[2,3-d]pyrimidine 7a-f, 9, 10a-f, 12a,b, 14a-d and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine 8a-f derivatives were designed based on their structural similarity to a previously described oxazole VEGFR-2 back pocket binding fragment. The designed compounds were synthesized and screened for their in vitro VEGFR-2 inhibitory activity where they exhibited good to moderate nanomolar inhibition with improved ligand efficiencies. 8b and 10c (IC50 = 38.72 ± 1.7 and 41.40 ± 1.8 nM, respectively) were equipotent to sorafenib and 6a, 6c, 7f, 8a, 8c, 10b, 10f, 12b, 14c and 14d showed good activity (IC50 = 43.31–98.31 nM). The furotriazolopyrimidines 8a-c and furopyrimidine derivative 10c were further evaluated for their in vitro antiproliferative activity against human umbilical vein endothelial cells (HUVECs) where 8b showed higher potency than sorafenib and resulted in cell cycle arrest at G2/M phase whereas 8c revealed good antiproliferative activity with cell cycle arrest at G1 phase. Moreover, 8a-c and 10c showed significant inhibitory effects on the invasion and migration of HUVECs. Molecular docking study was conducted to gain insight about the potential binding mode. The furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives 8b and 8c represent interesting starting point for antiangiogenic compounds based on their activity and favorable drug likeness profiles.

Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions

A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.

Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo[2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-π interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N1, N1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFRL858R reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists.

One-pot synthesis of substituted 2-amino-3-furonitriles

Solvent-free reaction of substituted a-haloketones with malononitrile in the presence of diethylamine provides an efficient one-pot synthesis of 2-amino-5-aryl (alkyl)-3-furonitriles in high yield.

COMPOUND FOR INHIBITING TYROSINE KINASE ACTIVITY OF DDR2 PROTEIN

A new furopyrimidine compound, their pharmaceutically acceptable salt, and a tyrosine kinase activity inhibitor. The furopyrimidine compound is a compound defined by chemical formula 1, 2, 3 or 4, on their precursor, and can exist as a form of free base or in an acid-addition salt. Since the furopyrimidine compound has an effect of inhibiting activity of DDR2 tyrosine kinase, it can be used in treating illnesses caused by the DDR2 tyrosine kinase activity such as hepatocirrhosis, rheumatoid arthritis or cancer.

Novel 4-amino-furo[2,3-d]pyrimidines as Tie-2 and VEGFR2 dual inhibitors

A novel class of furo[2,3-d]pyrimidines has been discovered as potent dual inhibitors of Tie-2 and VEGFR2 receptor tyrosine kinases (TK) and a diarylurea moiety at 5-position shows remarkably enhanced activity against both enzymes. One of the most active compounds, 4-amino-3-(4-((2-fluoro-5-(trifluoromethyl) phenyl)amino-carbonylamino)phenyl)-2-(4-methoxyphenyl)furo[2,3-d]pyrimidine (7k) is 3 nM on both TK receptors and the activity is rationalized based on the X-ray crystal structure.

NOVEL CHEMICAL COMPOUNDS

The present invention relates generally to inhibitors of the kinases, such as GSK-3, and more particularly to fused pyrimidine compounds.

4-Acylamino-6-arylfuro[2,3-d]pyrimidines: Potent and selective glycogen synthase kinase-3 inhibitors

Modeling studies of a furo[2,3-d]pyrimidine GSK-3 hit compound 1 superimposed onto the X-ray crystal structure of a legacy pyrazolo[3,4-c] pyridazine GSK-3 inhibitor 2 led to the identification of 4-acylamino-6- arylfuro[2,3-d]pyrimidine template 3. Synth