62806-33-1

Upstream product

• 13803-39-9 5-phenylfuran-2-carbaldehyde 
• 141-82-2 malonic acid 
• 98-80-6 phenylboronic acid 
• 22078-90-6 2-hydroxymethyl-5-phenylfuran 
• 34265-60-6 (E)-3-(5-Phenyl-furan-2-yl)-acrylic acid ethyl ester 
• 1018586-19-0 2-(chloromethyl)-5-phenylfuran 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 100-34-5 benzene diazonium chloride 
• 98-01-1 furfural 
• 39511-08-5 (E)-3-(2-furanyl)-2-propenal 
• 62-53-3 aniline 

Downstream Products

• 107450-78-2 3,6-Dichloro-2-phenylthieno<3,2-b>furan-5-carboxylic acid chloride 
• 912369-19-8 tert-butyl (3S)-3-[(7-cyano-2-phenylfuro[3,2-c]pyridin-4-yl)amino]piperidine-1-carboxylate 
• 912369-18-7 4-chloro-2-phenylfuro[3,2-c]pyridine-7-carbonitrile 
• 912369-17-6 7-bromo-2-phenylfuro[3,2-c]pyridin-4(5H)-one 
• 188437-82-3 2-phenylfuro[3,2-c]pyridin-4(5H)-one 
• 111252-83-6 (E)-N,N-Dimethyl-3-(5-phenyl-furan-2-yl)-acrylamide 
• 111252-42-7 (E)-3-(5-Phenyl-furan-2-yl)-acryloyl chloride 
• 129626-54-6 4-[(E)-2-(5-Phenyl-furan-2-yl)-vinyl]-benzoic acid ethyl ester 
• 40025-25-0 (E)-5-phenyl-2-(2-phenylvinyl)furan 

Relevant academic research and scientific papers

Adventures in Scaffold Morphing: Discovery of Fused Ring Heterocyclic Checkpoint Kinase 1 (CHK1) Inhibitors

Checkpoint kinase 1 (CHK1) inhibitors are potential cancer therapeutics that can be utilized for enhancing the efficacy of DNA damaging agents. Multiple small molecule CHK1 inhibitors from different chemical scaffolds have been developed and evaluated in clinical trials in combination with chemotherapeutics and radiation treatment. Scaffold morphing of thiophene carboxamide ureas (TCUs), such as AZD7762 (1) and a related series of triazoloquinolines (TZQs), led to the identification of fused-ring bicyclic CHK1 inhibitors, 7-carboxamide thienopyridines (7-CTPs), and 7-carboxamide indoles. X-ray crystal structures reveal a key intramolecular noncovalent sulfur-oxygen interaction in aligning the hinge-binding carboxamide group to the thienopyridine core in a coplanar fashion. An intramolecular hydrogen bond to an indole NH was also effective in locking the carboxamide in the preferred bound conformation to CHK1. Optimization on the 7-CTP series resulted in the identification of lead compound 44, which displayed respectable drug-like properties and good in vitro and in vivo potency.

2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids are novel substrates of phenylalanine ammonia-lyase

Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, 1H-NMR and 13C-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-la) para-Br (rac-lb) or Cl para or ortho (rac-lc, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10. The Japan Institute of Heterocyclic Chemistry.

SUBSTITUTED HETEROCYCLES AND THEIR USE AS CHK1, PDK1 AND PAK INHIBITORS

This invention relates to novel compounds of Formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds possess CHK1 kinase inhibitory activity, PDK1 inhibitory activity and Pak kinase inhibitory activity and are accordingly useful in the treatment and/or prophylaxis of cancer.

Non-thiol farnesyltransferase inhibitors: N-(4-tolylacetylamino-3- benzoylphenyl)-3-arylfurylacrylic acid amides

We have designed arylfurylacryl-substituted benzophenones as non-thiol farnesyltransferase inhibitors utilizing a novel aryl binding site of farnesyltransferase. These compounds display activity in the low nanomolar range. We have designed arylfurylacryl-

Structure-activity relationships of novel anti-malarial agents part 8. Effect of different central aryls in biarylacryloylaminobenzophenones on antimalarial activity

Replacement of the 2,5-disubstituted furyl residue present in the known antimalarial agents 8 by other aryl residues resulted in a more or less reduced antimalarial activity in most cases. The only exemption was the 2,4-thienylene compound 11a displaying activity with an IC50 value of 120 nM. In conclusion, the 2,5-furylene compound 8e remains to represent the most active antimalarial agent in this series of farnesyltransferase inhibitors.

Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides

In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties.

Synthesis of 2-arylfuro[3,2-c]pyridines and their derivatives

A series of 2-arylfuro[3,2-c]pyridines was synthesized. 3-(5-Aryl-2-furyl)propenoic acids 1a-1h were converted to the acid azides 2a-2h, which in turn were cyclized to give 2-arylfuro[3,2-c]pyridine-4(5H)-ones 4a-4h by heating in Dowtherm. The pyridones 4a-4f were aromatized with phosphorus oxychloride to the 2-aryl-4-chlorofuro[3,2-c]pyridines 5a-5f, which were reduced with zinc and acetic acid to the title compounds 6a-6f. Reacted with phosphorus(V) sulfide, the pyridones 4a-4f yielded the corresponding thiones 7a-7f.

ARYLATION OF FURAN COMPOUNDS BY ARENEDIAZONIUM SALTS

3-(5-Aryl-2-furyl)acrylic acids were obtained by the reaction of 5-arylfurfurals with malonic acid.They were arylated by diazonium salts with decarboxylation and the formation of 5-aryl-2-styrylfurans.The latter were also obtained by the interaction of furylacrolein with diazonium salts.This reaction also gave 3-(5-aryl-2-furyl)acroleins and the corresponding arylfurylacrylic acids, which were arylated again with the release of CO2 and the formation of 5-aryl-2-styrylfurans. 3-(5-Aryl-2-furyl)acroleins were also synthesized by the condensation of 5-arylfurfurals with acetaldehyde under phase-transfer conditions.The s-trans configuration of the furan ring and the exocyclic double bond were established in the obtained compounds by the PMR method.

CATALYTIC ARYLATION OF FURFURAL BY ARENEDIAZONIUM SALTS

A series of 5-arylfurfurals were obtained by the reaction of furfural with arenediazonium chlorides in the presence of cupric chloride or ferrous chloride.The optimum reaction conditions depend on the nature of the substituent in the aromatic ring of the