28447-81-6

Usage

Chemical compound

6-Chloro-3-cyanocoumarin

Family

Coumarin

Properties

Fluorescent molecule
Contains a cyanide group and a chlorine atom

Uses

Used as a fluorescent probe and indicator in biochemical and biomedical research
Suitable for applications in cellular imaging, fluorescence microscopy, and fluorescent labeling of biological molecules
Potential applications in the development of sensors and assays for detecting various analytes and biomolecules in biological systems
Versatile uses in scientific research and bioanalytical applications due to its distinctive chemical and optical properties

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
• 109-77-3 malononitrile 
• 91357-43-6 α-cyanoketene 3,5-dithiaheptane 
• 476479-85-3 6-Chloro-2-imino-2H-chromene-3-carbonitrile 

Relevant academic research and scientific papers

Supramolecular synthesis of coumarin derivatives catalyzed by a coordination-assembled cage in aqueous solution

A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages’ cavity is crucial for their applications in supramolecular catalysis.

3-substituted coumarin derivative and application and GPR35 receptor agonist

The invention discloses a 3-substituted coumarin derivative and a pharmaceutically acceptable salt, a solvate, a hydrate or a crystal form. The compound of the invention generally exhibits high agonistic activity against human G protein-coupled receptor 35 (GPR35) and is specific agonists of the human GPR35 receptor. The compound provided by the invention is an active ligand of the novel GPR35 receptor, and the compound and the pharmaceutically acceptable salt, the solvate, the hydrate or the crystal form thereof generally exhibit higher activity and good selectivity to the human GPR35. The 3-substituted coumarin derivative is the specific agonist of the GPR35 receptor and can be used in the preparation of a medicament for treating, preventing and inhibiting a disease mediated by the GPR35receptor.

Discovery of 2H-Chromen-2-one Derivatives as G Protein-Coupled Receptor-35 Agonists

A family of 2H-chromen-2-one derivatives were identified as G protein-coupled receptor-35 (GPR35) agonists using dynamic mass redistribution assays in HT-29 cells. The compounds with 1H-tetrazol-5-yl in 3-substituted position displayed higher potency than the corresponding carboxyl analogs, and the hydroxyl group in the 7-position also played an important role in GPR35 agonistic activity. 6-Bromo-7-hydroxy-8-nitro-3-(1H-tetrazol-5-yl)-2H-chromen-2-one (50) was found to be the most potent GPR35 agonist with an EC50 of 5.8 nM. Calculating the physicochemical properties of compounds with moderate to high potency suggested that compounds 30, 50, and 51 showed good druggability. This study provides a novel series of GPR35 agonists, and compound 50 may be a powerful tool to study GPR35.

Iodine-mediated one-pot synthesis of 3-cyanocoumarins and 3-cyano-4-methylcoumarins

2-Hydroxybenzaldehydes 1a-e on reaction with malononitrile (2) in the presence of iodine as catalyst give 3-cyanocoumarins 3a-e in one step under thermal heating as well as under microwave irradiation. The latter conditions are much more efficient in terms of time (2-5 min) and yield as compared to the thermal conditions (2-2.5 h). Following a similar procedure, 3-cyano-4-methylcoumarins 3f-i were also prepared by the reaction of 2-hydroxyacetophenones 1f-i with 2.

FeCl3-catalyzed cascade reaction: An efficient approach to functionalized coumarin derivatives

An efficient and environmentally benign synthesis of 3-substituted or 3,4-disubstituted coumarins was accomplished via iron(III) chloride-catalyzed cascade reactions of salicylaldehydes and activated methylene compounds. The reaction preceded cleanly under mild reaction conditions to provide the desired coumarin derivatives in good to excellent yields.

Titanium tetraisopropoxide promoted rreactions for the synthesis of substituted coumarins

Substituted coumarins are synthesized by the reaction of salicylaldehyde derivatives with malonitrile, isopropyl cyanoacetate or diisopropyl malonate promoted by Ti(O-i-Pr)4. When i-PrOH is used as a solvent, these reactions proceeded by the catalytic amount of Ti(O-i-Pr)4 (～0.1 equivalent).

Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals

Hydrobromic acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other acids (including Lewis and Bronsted acids), the remarkable catalytic performance of hydrobromic acid in catalytic a

Copper(II)-catalyzed C-C bond-forming reactions of α-electron- withdrawing group-substituted ketene S,S-acetals with carbonyl compounds and a facile synthesis of coumarins

A new catalytic C-C bond-forming reaction has been developed. Catalyzed by cheap and commercially available copper(II) bromide (CuBr2; 10 mol%), the reactions of α-electron-withdrawing group (EWG)-substituted ketene S,S-acetals with aldehydes or ketones in acetonitrile at room temperature gave a variety of densely functionalized coupling products in excellent yields (80-98%). Based on this catalytic process, coumarin derivatives were efficiently synthesized when salicylaldehydes were selected as the carbonyl components.

One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water

Chloro-, hydroxy-, methoxy-, and tert-butyl-substituted 3-carboxycoumarins have been prepared by one-pot procedure by reaction of suitably substituted salicylaldehydes with malononitrile in water. The over-all yields are high and the protocol does not require organic solvents.

Samarium (III) triiodide catalysed reaction of salicylaldehydes with active methylene compounds

The unambiguous synthesis and isolation of 2-oxo-2H-1-benzopyran derivatives are described. The Knoevenagel condensation of 2-hydroxy benzaldehydes with active methylene compounds catalysed by samarium triiodide resulted in coumarium derivatives in fair yields under refluxing conditions.