14006-16-7

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 555-16-8 4-nitrobenzaldehdye 
• 520-45-6 Dehydracetic acid 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 

Downstream Products

• 120421-97-8 7-methyl-2-(4-nitrophenyl)-pyrano<4,3-b>pyran-4(H), 5(H)-dione 

Relevant academic research and scientific papers

Design, synthesis and neuropharmacological evaluation of new 2,4-disubstituted-1,5-benzodiazepines as CNS active agents

Benzodiazepines (BZDs) represent a class of privilege scaffold in the modern era of medicinal chemistry as CNS active agents and BZD based drugs are used to treat different psychotic disorders. Inspired from the therapeutic potential of BZDs as promising CNS active agents, in the present work three different series of 1,5-benzodiazepines bearing various substitutions at position 2 and 4 of the benzodiazepine core were synthesized by condensing different substituted chalcones with o-phenylenediamine in the presence of piperidine as a base catalyst. Structural characterization of title compounds was done by using various analytical techniques such as IR, NMR, elemental analysis and mass spectral data. All the synthesized compounds (9a-d, 10a-e and 11a-c) were subjected to in vivo neuropharmacological studies to evaluate their CNS depressant and antiepileptic activity. Results of in vivo evaluation data showed that analogue 11b exhibited potent CNS depressant activity which was comparable to the standard drug diazepam. Compounds 10b and 10c displayed significant antiepileptic activity however they were less potent than the standard drug phenobarbitone. Molecular docking studies were performed using MOE software to find the interaction pattern and binding mode at the GABAA receptor (PDB Id: 6HUP). The results of the docking studies were in good agreement with the observed in vivo activity and revealed the satisfactory binding mode of the compounds within the binding site of the protein. The docking scores for the most promising candidates 10c, 11b and Diazepam were found to be ?9.18, ?9.46 and ?9.88, respectively. Further, the compounds showed compliance with the Lipinski's ‘rule of five’ and exhibited favourable drug-likeness scores. The identified leads can be explored further for the design and development of new BZD based psychotropic agents.

A novel and efficient synthetic method of benzo[f]chromen-1-ones and phenyl-4h-chromen-4-one through photooxidative cyclization of 6-[(E)-2-arylvinyl]-4H-pyran-4-ones and 6-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-4H-pyran-4-one

A rapid and efficient microwave-assisted transformation of 2-pyrones into 4-pyrones is reported. Then, a new photocatalytic oxidative cyclization of 6-[(E)-2-arylvinyl]-2-methyl-4H-pyran-4-ones and 2-methyl-6-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-4H-pyran-

Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I)

When exposed to electrophiles, human colorectal cancer cells (HCT116) counteract oxidative stress through activating NF-E2-related factor 2 (Nrf2)/antioxidant response element (ARE) pathway. To identify new activators, luciferase reporter gene assay was used to screen in-house database of our laboratory, leading to a novel α-pyrone compound 1 as a hit. 2 with 2-fluoro phenyl group exhibited the strongest ARE inductive activity in the first round structure-activity relationship (SAR) study. Biological studies showed the compound induced nuclear translocation of Nrf2 preceded by phosphorylation of ERK1/2. The data encouraged us to use 2 as lead and 20 derivatives were synthesized to discuss a more detailed SAR, leading to a more potent compound 9, which can be the starting compound for further modification.

Discovery of 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-phenyl-(E)-2,3,6,7-tetrahydro-1,4-thiazepines as a new series of apoptosis inducers using a cell- and caspase-based HTS assay

We report the discovery of 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-(4-methylphenyl)-(E)-2,3,6,7-tetrahydro-1,4-thiazepine (2a) as an inducer of apoptosis using our proprietary cell- and caspase-based HTS assay. Through structure activity relationship

A facile synthesis of 3,4-dihydro-2-pyronyl-1,5-benzodiazepine derivatives

The reaction of o-phenylenediamine with 3-cinnamoyl-4-hydroxy-6-methyl-2-pyrones (3a-i, chalcone analogs of dehydroactic acid) in ethanol-acetic acid provides a facile method for the synthesis of 3,4-dihydro-2-pyronyl-1,5-benzodiazepine derivatives (2a-i).