38322-74-6

Usage

InChI:InChI=1/C13H12O5/c1-3-17-13(15)12-7-10(14)9-5-4-8(16-2)6-11(9)18-12/h4-7H,3H2,1-2H3

Upstream product

• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 95-92-1 oxalic acid diethyl ester 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 23866-72-0 ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate 
• 74-88-4 methyl iodide 

Downstream Products

• 23915-78-8 7-methoxy-4(H)-oxo-1-benzopyran-2-carboxylic acid 
• 79480-10-7 N-phenyl-7-methoxy-4(H)-oxo-1-benzopyran-2-carboxamide 
• 197388-36-6 [3-(4-Chloro-3-nitro-phenoxy)-propyl]-(7-methoxy-chroman-2-ylmethyl)-amine 
• 197388-32-2 (7-Methoxy-chroman-2-ylmethyl)-[3-(2-methyl-3-nitro-phenoxy)-propyl]-amine 
• 197388-38-8 2-Chloro-5-{3-[(7-methoxy-chroman-2-ylmethyl)-amino]-propoxy}-phenylamine 
• 197388-40-2 5-{3-[(7-Methoxy-chroman-2-ylmethyl)-amino]-propoxy}-2-methyl-phenylamine 
• 197388-42-4 3-{3-[(7-Methoxy-chroman-2-ylmethyl)-amino]-propoxy}-phenylamine 
• 197388-31-1 (7-methoxy-chroman-2-ylmethyl)-(3-phenoxy-propyl)-amine 
• 197388-29-7 (7-Methoxy-chroman-2-ylmethyl)-(4-phenyl-butyl)-amine 
• 197388-27-5 (7-Methoxy-chroman-2-ylmethyl)-(3-phenyl-propyl)-amine 
• 197388-25-3 (7-Methoxy-chroman-2-ylmethyl)-phenethyl-amine 

Relevant academic research and scientific papers

Synthesis and evaluation of chromone-2-carboxamido-alkylamines as potent acetylcholinesterase inhibitors

Alzheimer’s disease (AD) is considered one of the greatest global public burdens. Pathophysiology of AD is proposed to be associated with reduced levels of the neurotransmitter acetylcholine (ACh). Cholinesterase enzymes, namely acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) cleave ACh via hydrolysis. Cholinesterase inhibitors (ChEIs) are the main group of drugs currently used for the treatment of AD. Novel chromone-2-carboxamido-alkylamines (7–18) were designed, synthesized, and evaluated for cholinesterase inhibitory activity. The compounds exhibited potent AChE inhibitory activities at micromolar range (IC50 0.09–9.16 μM) and demonstrated weak BChE inhibitory activities (IC50 12.09–44.56 μM). Compound 14 (IC50 0.09 ± 0.02 μM) was the most potent AChEI in this series; it showed higher activity than the clinical used drug tacrine. Enzyme kinetic study suggested that 14 was an uncompetitive inhibitor. Molecular docking study revealed that 14 was a dual-binding site inhibitor. Compound 14 did not induce any concentration-related cytotoxic effect against SH-SY5Y cells. It also showed neuroprotective effect in the cell line. Chromone-2-carboxamido-alkylamines can be promising lead compounds for development of anti-Alzheimer’s agents.

SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY

Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

SUBSTITUTED CHROMANES AND METHOD OF USE

The invention provides for compounds of formula (I), wherein R1, X, Y, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, m, and R" have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions mediated and modulated by CFTR, including cystic fibrosis, Sj?gren's syndrome, pancreatic insufficiency, chronic obstructive lung disease, and chronic obstructive airway disease. Also provided are pharmaceutical compositions comprised of one or more compounds of formula (I).

Bifunctional compounds targeting both D2and non-α7 nACh receptors: Design, synthesis and pharmacological characterization

We designed, prepared and tested a set of structural analogs 1-4 as new hybrid compounds by incorporating, through a common alkyl chain of variable length, the pharmacophoric elements of N-n-alkyl nicotinium salts (non-α7 nicotinic acetylcholine receptors antagonists) and of 7-hydroxy-2-(aminomethyl)chromanes (dopaminergic D2receptor agonists). The target compounds, which were assayed in binding experiments and electrophysiological, functional and Erk1/2 activation tests, essentially combined the pharmacological profiles of their individual receptor ligands. Among the studied derivatives, hybrid 2, one of the shortest homologs, in addition to the antagonist nicotinic profile similar to the other three congeners, behaved as a high affinity ligand at the investigated heteromeric nAChRs and as a low efficacy agonist at D2Rs. These bifunctional derivatives represent novel pharmacological tools in the study of nicotine addiction.

Synthesis, spectroscopic characterization and X-ray structure of novel 7-methoxy-4-oxo-N-phenyl-4H-chromene-2-carboxamides

The chromone scaffold has been found to be an important tool in the drug discovery process through its relevant pharmacological activities. Chromone carboxamide derivatives synthesized within our group have shown noteworthy results as inhibitors of monoam

Biomimetic type approach to the tricyclic core of xyloketals. Application to a short, stereocontrolled synthesis of alboatrin and first synthesis of xyloketal G

A convenient approach to the linear tetrahydrofurano benzopyran ring system of xyloketals is described. An orthoester Claisen rearrangement of a chromenol and an intra-molecular cationic cyclization are the key steps in the synthesis. A short, stereocontrolled and high yield synthesis of the phytotoxic metabolite alboatrin was achieved employing this strategy. A unique case of Lewis acid catalyzed isomerization of epi-alboatrin to alboatrin was observed. Subsequently this methodology was extended for the first total synthesis of xyloketal G, where a one pot reaction of three steps viz., acetylation, isomerization and demethylation occurred during acetylation of a mixture of nor-o-methyl xyloketal G and nor-o-methyl epi xyloketal G in presence of AlCl3 to furnish xyloketal G in very good overall yield.

CHROMEN-4-ONE DERIVATIVES

The invention relates to chromen-4-one derivatives, the production thereof, and the use of the same for the care, preservation or improvement of the general state of the skin or especially the hair, and for the prophylaxis of time-induced and/or light-induced ageing processes of the human skin or especially human hair. The invention also relates to preparations with an active content of such chromen-4-one derivatives.

Optimization of chromone-2-carboxamide melanin concentrating hormone receptor 1 antagonists: Assessment of potency, efficacy, and cardiovascular safety

Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel.

Chromone derivatives which bind to human hair

Chromone derivatives bearing a quaternary ammonium functionality which bind to human hair were synthesised. The radical scavenging activity, according to the DPPH assay, of the chromone derivatives is considerably lower compared with flavonoids. The compounds show interesting UV absorption properties that depend on the position of a methoxy substituent. A bathochromic shift of 29 nm was observed when the methoxy group on the ammonium salts were shifted from position 7 to position 6.

Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor

The present invention is directed to compounds of formula (I), which antagonize of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.