665000-66-8

Usage

Amino Group

Contains an amino group (-NH2) which can participate in various chemical reactions and interactions.

Fluorophenyl Group

Includes a fluorophenyl group (C6H4F) which can impart specific chemical properties and reactivity.

Hydroxymethyl Group

Contains a hydroxymethyl group (-CH2OH) which can serve as a functional group in various chemical reactions.

Pyrano Ring Structure

Features a pyrano ring structure, specifically a dihydropyrano[3,2-b]pyran, which can confer unique chemical and biological properties.

Carboxylic Nitrile Group

Attached to the pyrano ring, adding a carboxylic nitrile group (-C≡N), which can contribute to the compound's overall chemical reactivity and properties.

Potential Applications

Has potential applications in medicinal chemistry due to its diverse chemical functionalities, serving as a basis for developing pharmaceuticals or as a research tool for understanding biological processes.

Intriguing Structure

The compound's unique structure and properties make it an intriguing target for further study and potential practical applications.

Upstream product

• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 2698-43-3 2-(2-fluorobenzylidene)malononitrile 
• 446-52-6 2-Fluorobenzaldehyde 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Synthesis and biological assessment of KojoTacrines as new agents for Alzheimer’s disease therapy

In view of the multifactorial nature of Alzheimer’s disease (AD), multitarget small molecules (MTSM) represent the most potent and attractive therapeutic strategy to design new drugs for Alzheimer’s disease therapy. The new MTSM KojoTacrines (KTs) were designed and synthesized by juxtaposition of selected pharmacophoric motifs from kojic acid and tacrine. Among them, 11-amino-2-(hydroxymethyl)-12-(3-methoxyphenyl)-7,9,10,12-tetrahydropyrano [2',3':5,6] pyrano[2,3-b]quinolin-4(8H)-one (KT2d) was identified as less-hepatotoxic than tacrine, at higher concentration, a moderate, but selective human acetylcholinesterase inhibitor (IC50 = 4.52 ± 0.24 μM), as well as an antioxidant agent (TE = 4.79) showing significant neuroprotection against Aβ1–40 at 3 μM and 10 μM concentrations. Consequently, KT2d is a potential new hit-ligand for AD therapy for further biological exploration.

SiO2-OSO3H nanoparticles: An efficient, versatile and new reagent for the one-pot synthesis of 2-amino-8-oxo-4,8-dihydropyrano[3,2-b] pyran-3-carbonitrile derivatives in water, a green protocol

In a one-pot three-component reaction, an aromatic or aliphatic aldehyde, malononitrile and 5-hydroxy-2-hydroxymethyl-4H-pyran-4-one were condensed for the synthesis of 2-amino-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile derivatives in the presence of nano-silica sulfuric acid (SiO 2-OSO3H nanoparticles) in improved yields. The catalyst is recoverable by simple filtration and can be used in the subsequent reactions.

Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b] pyran-3-carbonitrile scaffolds in aqueous media: A complementary 'green chemistry' tool to organic synthesis

A green and simple approach to assembling of 2-amino-4,8-dihydropyrano[3,2- b]pyran-3-carbonitrile scaffolds via three-component reaction of kojic acid, malononitrile, and aromatic aldehydes in aqueous media under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this green procedure.