41873-72-7

Usage

Classification

Chromene derivative

Structure

Contains a chromene ring with a carbonyl group at the 3-position

Use

Organic synthesis, reagent in chemical reactions

Application

Production of pharmaceuticals, agrochemicals, and other fine chemicals

Versatility

Known for versatile reactivity

Intermediate

Used in the synthesis of biologically active compounds and heterocyclic molecules

InChI:InChI=1/C10H7ClO2/c11-10(12)8-5-7-3-1-2-4-9(7)13-6-8/h1-5H,6H2

Upstream product

• 22649-28-1 2H-chromene-3-carboxylic acid 
• 10185-00-9 Chromene-3-carboxamide 
• 90-02-8 salicylaldehyde 
• 57543-66-5 2H-chromene-3-carbonitrile 
• 151510-35-9 tert-butyl 2H-1-chromene-3-carboxylate 

Downstream Products

• 83823-11-4 2H-Chromene-3-carboxylic acid pyridin-3-ylamide 
• 83823-18-1 2H-Chromene-3-carboxylic acid butylamide 
• 83823-16-9 2H-Chromene-3-carboxylic acid (2-diethylamino-ethyl)-amide 
• 338761-04-9 N-(4-methoxyphenyl)-2H-chromene-3-carboxamide 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C-H Functionalization

Ruthenium-catalyzed oxidative annulation of 2H-chromene-3-carboxamides with alkynes has been achieved by using the directing group nature of amide in the presence of Cu(OAc)2·H2O as an oxidant and AgNTf2 as an additive. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be harnessed. High regioselectivity was achieved in the case of unsymmetrical alkynes. In addition, we have also accomplished double C-H activation by employing an excess of alkyne, where both annulation and hydroarylation took place regio- and stereoselectively in one pot, with the catalyst playing a dual role. While the first C-H functionalization could involve Ru-N covalent bond, the second C-H functionalization most likely involves Ru-O coordinate bond. The structures of key products are confirmed by X-ray crystallography.

Design and synthesis of chiral 2H-chromene-N-imidazolo-amino acid conjugates as aldose reductase inhibitors

Aldose reductase (ALR2) inhibitors provide a viable mode to fight against diabetic complications. ALR2 exhibit plasticity in the active site vicinities and possible shifts in the nearby two supporting alpha helices. Therefore, a novel series of amino acid conjugates of chromene-3-imidazoles (13–15) were designed and synthesized based on natural isoflavonoids. The compounds were identified on the basis of spectral (1H NMR,13C NMR and MS) data and tested in vitro for ALR2 inhibitory activity with an IC50value ranges from 0.031 ± 0.082 μM to 4.29 ± 0.55 μM. Our in silico and biochemical studies confirmed that 15e has the best inhibition activity among the synthesized compounds with a high selective index against the Aldehyde reductase (ALR1). Supplementation of 15e to STZ induced rats decreased the blood glucose levels and delayed the progression of cataract in a dose-dependent manner. The present study thus provides novel series of compounds with a promising inhibitor to prevent or delay the cataract progression.

Substituted chromenes as potent, orally active 5-lipoxygenase inhibitors

A series of chromene derivatives was synthesized and evaluated for their in vitro and ex vivo 5-lipoxygenase (5-LO) inhibitory activity. These compounds were prepared by condensation of appropriate salicyl aldehydes with α,β-unsaturated carbonyl compounds

Pharmacomodulation d'adrenolytiques α en serie benzopyrannique

Pharmacomodulation of α-adrenergic blocking agents by a series of benzopyrans.The N-methylpiperidine fragment was associated with four oxygenated heterocycles of the benzopyran ring system.Two different synthesis pathways were used in each case.Twenty intermediate derivatives and four aminomethylated derivatives whose structures were established by spectroscopic data are described.The pharmacological investigation demonstrates the interest of these compounds on the α-adrenergic receptors in light of their activities and selectivities. α1-adrenergic blocking agents / α2-adrenergic blocking agents / piperidinomethyl chromone, chromene and chromane

Chromene and Chroman 3-Carboxamides and Some Related Compounds as a New Class of Centrally Acting Agents

A number of chromene-3-carboxamides (7), 3-Aminochromans (11) and 3-aminomethylchromans (9) have been synthesized.Chromene-3-carboxamides have been found to exhibit strong central muscle relaxant activity compared to mephesin.