14742-32-6

Usage

Uses

Used in Organic Synthesis:
2-AMINO-5-PHENYL-3-FURONITRILE is used as a building block in organic synthesis for the creation of various biologically active molecules. Its unique structure and properties make it a valuable component in the development of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-AMINO-5-PHENYL-3-FURONITRILE is used as a key intermediate in the synthesis of drugs with therapeutic potential. Its ability to form a wide range of derivatives allows researchers to explore its potential in the development of new medications.
Used in Anti-inflammatory and Analgesic Applications:
2-AMINO-5-PHENYL-3-FURONITRILE has been studied for its potential pharmacological properties, including its anti-inflammatory and analgesic effects. Researchers are investigating its ability to modulate inflammatory pathways and alleviate pain, which could lead to the development of new treatments for various conditions.

InChI:InChI=1/C11H8N2O/c12-7-9-6-10(14-11(9)13)8-4-2-1-3-5-8/h1-6H,13H2

Upstream product

• 14476-72-3 2-(2-oxo-2-phenylethyl)malononitrile 
• 70-11-1 α-bromoacetophenone 
• 109-77-3 malononitrile 
• 100805-20-7 5-Amino-2-phenyl-2,3-dihydro-furan-2,4-dicarbonitrile 
• 5153-67-3 nitrostyrene 
• 98-86-2 acetophenone 
• 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 

Downstream Products

• 125041-34-1 4-Amino-2-(4-chloro-phenyl)-1,3-dioxo-7-phenyl-2,3-dihydro-1H-isoindole-5-carbonitrile 
• 125041-33-0 4-Amino-2-(4-methoxy-phenyl)-1,3-dioxo-7-phenyl-2,3-dihydro-1H-isoindole-5-carbonitrile 
• 220696-22-0 5-phenyl-2-(1-pyrrolyl)-3-furonitrile 
• 943230-32-8 6-phenylfuro[2,3-d]pyrimidin-4(3H)-one 
• 1073136-05-6 rac-5-Bromo-6-phenyl-4-(piperidin-3-yloxy)furo[2,3-d]pyrimidine 
• 1073136-06-7 (+/-)-4-{3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester 
• 1073136-08-9 (+)-4-{(3S)-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester 
• 1073136-07-8 (-)-4-{(3R)-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester 
• 1073134-95-8 4-[(3S)-3-{[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}piperidin-1-yl]butanoic acid methyl ester 
• 1073136-09-0 cis/trans-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexanol 
• 1073136-04-5 tert-butyl rac-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]-1-piperidine carbamate 

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.

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity

Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.

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.

Novel, Cyclically Substituted Furopyrimidine Derivatives and Use Thereof

The present application relates to novel, cyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.

SUBSTITUTED FUROPYRIMIDINES AND USE THEREOF

The present application relates to novel substituted furopyrimidine derivatives, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, especially for the treatment and/or prophylaxis of cardiovascular diseases.

TRISUBSTITUTED FUROPYRIMIDINES AND USE THEREOF

The invention relates to the novel 4,5,6-trisubstituted furo[2,3-d]pyrimidine derivatives of formula (I), to methods for their production, their use in the treatment and/or prophylaxis of diseases and their use in the production of drugs for the treatment

Identification, SAR studies, and X-ray Co-crystallographic analysis of a novel furanopyrimidine aurora kinase a inhibitor

Herein we reveal a simple method for the identification of novel Aurora kinase A inhibitors through substructure searching of an in-house compound library to select compounds for testing. A hydrazone fragment conferring Aurora kinase activity and heterocy

Fused Bicyclic and Tricyclic Pyrimidine Compounds as Tyrosine Kinase Inhibitors

Fused bicyclic or tricyclic compounds of formula (I): wherein A, B, C, X, Y, m, and n are defined herein. Also disclosed are a method for inhibiting EGFR kinase activity and a method for treating cancer with these compounds.

Novel, Acyclically Substituted Furopyrimidine Derivatives and Use Thereof

The present application relates to novel, acyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.