6296-04-4

Usage

Category

Chalcones

Functional Groups

Ketone and enone

Natural Occurrence

Found in the root of the turmeric plant

Medicinal Properties

a. Anti-inflammatory
b. Antioxidant

Potential Health Benefits

a. Treating arthritis
b. Treating cancer
c. Treating neurodegenerative diseases

Potential Use

As a food preservative due to its antimicrobial properties

Interest

Significant interest in both the scientific and medical communities for its potential health benefits.

Upstream product

• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 118-93-4 o-hydroxyacetophenone 
• 64531-95-9 nicotinoyl ethylcarbonate 
• 92163-69-4 2-Nicotinoyloxy-acetophenon 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 59-67-6 nicotinic acid 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 65485-86-1 2-furfurylidene-1-(2-hydroxy-phenyl)-3-pyridin-3-yl-propane-1,3-dione 
• 3327-27-3 2-(pyridine-3-yl)-4H-chromen-4-one 
• 65010-80-2 2-(5-pyridin-3-yl-isoxazol-3-yl)-phenol 
• 65010-79-9 2-(3-(pyridin-3-yl)isoxazol-5-yl)phenol 
• 60122-25-0 2-(5-(pyridin-3-yl)-1H-pyrazol-3-yl)phenol 
• 65485-87-2 1-(2-hydroxy-phenyl)-3-pyridin-3-yl-2-thiophen-2-ylmethylene-propane-1,3-dione 

Relevant academic research and scientific papers

Discovery and Optimization of Chromeno[2,3-c]pyrrol-9(2H)-ones as Novel Selective and Orally Bioavailable Phosphodiesterase 5 Inhibitors for the Treatment of Pulmonary Arterial Hypertension

Phosphodiesterase 5 (PDE5) inhibitors have been used as clinical agents to treat erectile dysfunction and pulmonary arterial hypertension (PAH). Herein, we detail the discovery of a novel series of chromeno[2,3-c]pyrrol-9(2H)-one derivatives as selective and orally bioavailable inhibitors against phosphodiesterase 5. Medicinal chemistry optimization resulted in 2, which exhibits a desirable inhibitory potency of 5.6 nM with remarkable selectivity as well as excellent pharmacokinetic properties and an oral bioavailability of 63.4%. In addition, oral administration of 2 at a dose of 5.0 mg/kg caused better pharmacodynamics effects on both mPAP (mean pulmonary artery pressure) and RVHI (index of right ventricle hypertrophy) than sildenafil citrate at a dose of 10.0 mg/kg. These activities along with its reasonable druglike properties, such as human liver microsomal stability, cytochrome inhibition, hERG inhibition, and pharmacological safety, indicate that 2 is a potential candidate for the treatment of PAH.

Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure-activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

Raf kinase inhibitor based on chromone structure, and preparation method and uses thereof

The invention relates to the technical field of pharmaceutical chemistry, and more concretely relates to a group of chromone compounds (A), wherein R1-R10, X1 and X2 are defined in the description. The invention also discloses a preparation method of the

Synthesis and antimicrobial activity of 2-(pyridine-3-yl)-4 H -chromen-4-one derivatives

An efficiently synthesis of chromones via cyclodehydration of corresponding 1-(2-hydroxyphenyl)-3-(pyridine-3-yl)propane-1,3-dione is described under ultrasound irradiation. A series of novel 2-(pyridine-3-yl)-4H-chromen-4-one derivatives was confirmed on the basis of 1H-NMR, mass, IR spectral data, and elemental analysis. The synthesized compounds were evaluated for their antibacterial and antifungal activities. Most of the compounds were found to be comparable potent than the reference standard drugs. Utilization of ultrasound irradiation, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective.

PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF COMPLEX DISEASES AND THEIR DELIVERY BY INSERTABLE MEDICAL DEVICES

The present invention relates to polyphenol-like compounds that are useful for inhibiting VCAM-1 expression, MCP-1 expression and/or SMC proliferation in a mammal. The disclosed compounds are useful for regulating markers of inflammatory conditions, including vascular inflammation, and for treatment and prevention of inflammatory and cardiovascular diseases and related disease states.

Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: Towards a pharmacophore model for the nucleotide-binding domain

Our previous screen of flavones and related heterocycles for the ability to activate the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel indicated that UCCF-029, a 7,8-benzoflavone, was a potent activator. In the present study, we describe the synthesis and evaluation, using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated that benzannulation of the flavone A-ring at the 7,8-position greatly improved compound activity and potency for several flavonoids. Incorporation of a B-ring pyridyl nitrogen either at the 3- or 4-position also elevated CFTR activity, but the influence of this structural modification was not as uniform as the influence of benzannulation. The most potent new analogue, UCCF-339, activated wild-type CFTR with a Kd of 1.7 μM, which is more active than the previous most potent flavonoid activator of CFTR, apigenin. Several compounds in the benzoflavone panel also activated G551D-CFTR, but none were as active as apigenin. Pharmacophore modeling suggests a common binding mode for the flavones and other known CFTR activators at one of the nucleotide-binding sites, allowing for the rational development of more potent flavone analogues.

Synthesis and biological evaluation of flavonoids and related compounds as gastroprotective agents

Several analogs of the gastroprotective molecule flavone have been synthesized and evaluated for gastroprotective activity. A C2-C3 double bond and an intact C ring appear necessary for optimum activity. Activity can be retained by replacing the 2-phenyl substituent with other groups but is eliminated when this ring is moved from the 2- to the 3-position.

The Preparation of Flavones and their Derivatives. Part I. Flavones and 4-Thioflavones.

A series of polysubstituted flavones has been prepared with particular emphasis on 3',4',5',5,7-pentahydroxyflavone and its ether derivatives.The preparation of 4-thioflavones has been undertaken to provide intermediates for the preparation of 4-iminoflav