22252-92-2

Usage

InChI:InChI=1/C9H7NO/c10-6-9(7-11)8-4-2-1-3-5-8/h1-5,7,11H/b9-7+

Upstream product

• 107-31-3 Methyl formate 
• 140-29-4 phenylacetonitrile 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 56798-21-1 3,4,5,6-tetrahydroacridine-1,8(2H,7H)-dione 
• 143261-86-3 3-phenyl-7,8-dihydroquinoline-2,5(1H,6H)-dione 
• 143261-87-4 2-amino-3-phenyl-7,8-dihydroquinolin-5(6H)-one 
• 96216-43-2 1,3-Di-(2-cyan-2-phenyl-vinyl)-azulen 
• 21676-88-0 4-phenyl-2-thiophenecarboxylic acid 
• 21676-90-4 methyl 4-phenylthiophene-2-carboxylate 
• 2404-87-7 3-phenylthiophene 
• 82437-69-2 3-amino-4-phenylthiophene 
• 649757-57-3 3-amino-4-phenylthiophene-2-carboxylic acid 
• 1021878-19-2 E-β-bromo-α-phenylacrylonitrile 
• 1021878-17-0 Z-β-bromo-α-phenylacrylonitrile 
• 22252-94-4 3-cis-Amino-2-phenyl-acrylaldehyd 
• 22252-94-4 3-amino-2-phenylpropenal 
• 81920-97-0 1-(2-Cyan-2-phenyl-vinyl)-5-isopropyl-3,8-dimethyl-azulen 

Relevant academic research and scientific papers

Synthesis and seed germination stimulating activity of some imino analogs of strigolactones

Strigolactones are germination stimulants for seeds of the root parasitic weeds, Striga and Orobanche spp. The imino analog of GR24 showed moderate germination stimulating activity against the seeds of S. hermonthica. The seed germination stimulating activity of some phenyliminoacetates and phenyliminoacetonitriles was also examined. The degree of activity of the phenyliminoacetate was less than that of the phenylacrylates. On the other hand, the degree of activity of the phenyliminoacetonitrile was comparable to that of the phenylacrylonitriles. Among the tested compounds, the 3- pyridyliminoacetonitrile showed higher activity against the seeds of O. crenata than GR24. These findings demonstrate that it is not always essential to have the Michael acceptor of the C-D ring junction moiety which has been proposed to react with nucleophilic species presented at the target site to enhance the activity.

Synthesis and biological evaluation of N3-alkyl-thienopyrimidin-4-ones as mGluR1 antagonists

Metabotropic glutamate receptor subtype 1 (mGluR1) is a potential target for the treatment of neuropathic pain, and there has been much effort to discover mGluR1 antagonists. In this study, a series of N3-alkyl-thienopyrimidin-4-ones were prepared by introducing various alkyl and aryl groups to the N3- and 7-positions of the thienopyrimidin-4-one core structure, respectively, and their inhibitory activities against mGluR1 were biologically evaluated. Structure-activity relationship study revealed that the trans-4-methylcyclohexyl, cycloheptyl, and cyclooctyl groups at N3-position, and 2-fluorophenyl group at 7-position were most effective in potentiating the inhibitory activity of the thienopyrimidin-4-one derivatives against mGluR1. Among the synthesized compounds, 3-cyclooctyl-7-phenylthienopyrimidin-4-one and 3-cycloheptyl-7-(2-fluorophenyl)thienopyrimidin-4-one exhibited the most potent inhibitory activities with IC50 values of 115 and 107 nM, respectively.

THIENOPYRIMIDINONE DERIVATIVES AS mGluR1 ANTAGONISTS

Disclosed are thienopyrimidinone derivatives as antagonists that act on metabotropic glutamate receptor subtype 1. The thienopyrimidinone derivatives show pharmacological activity against metabotropic glutamate receptor-related diseases, including pain, such as neuropathic pain and migraine, psychiatric diseases, such as anxiety disorder and schizophrenia, urinary incontinence, and neurodegenerative diseases, such as Parkinson's disease and Alzheimer's disease. Also disclosed are methods for preparing the thienopyrimidinone derivatives, and pharmaceutical compositions containing the thienopyrimidinone derivatives as active ingredients.

Novel thienopyrimidinones as mGluR1 antagonists

There has been much attention to discover mGluR1 antagonists for treating various central nervous system diseases such as seizures and neuropathic pain. Thienopyrimidinone derivatives were designed, synthesized, and biologically evaluated against mGluR1. Among the synthesized compounds, 3-(4-methoxyphenyl)- 7-(o-tolyl)thienopyrimidin-4-one 30 exhibited the most potent inhibitory activity with an IC50 value of 45 nM and good selectivity over mGluR5. Also, the selective mGluR1 antagonist 30 showed marginal hERG channel activity (IC50 = 9.87 μM), good profiles to CYP isozymes, and a good pharmacokinetic profile. Overall, the compound 30 was identified as a selective mGluR1 antagonist with a good pharmacokinetic profile, which is probably devoid of cardiac side effect and drug-drug interactions. Therefore, the compound 30 can be expected to be broadly used as mGluR1 antagonistic chemical probe in in vitro and in vivo study for investigating CNS diseases.

α-CYANO-β-STYRENYL ESTERS FOR AMIDE BOND FORMATION

p-X-α-cyano-β-styrenyl esters (X = H, Cl, CF3, NO2) of N-benzyloxycarbonyl valine were prepared.The rate constant for amide formation with methyl valinate was assayed; it increases with increasing electron attracting power of the para substituent.The N-hydroxysuccinimidoyl ester and the p-H-α-cyano-β-styrenyl ester of valine have comparable reactivities.

Synthese d'amino-3 thiophenes a partir d'aryl- et d'hetaryl-acetonitrile (1)

Applying Fiesselman's condensation to α-hydroxymethylene nitriles the authors describe a synthesis of substituted aminothiophenes.