50329-91-4

Usage

Uses

4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a versatile reactant in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries. Its unique structure allows it to participate in a range of chemical reactions, leading to the formation of diverse products with potential applications.
Used in Pharmaceutical Industry:
4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a key intermediate in the synthesis of 2-aryl[1]benzopyrano[4,3-c]pyrazol-4(2H)-ones, which are compounds with potential biological activities. These synthesized compounds may exhibit properties such as anti-inflammatory, analgesic, and anti-cancer effects, making them valuable for the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a starting material for the preparation of biaryl lactones (benzo[c]chromen-6-ones). These compounds are of interest due to their potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Organic Chemistry:
4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is also used in the synthesis of N-monosubstituted 4-amino-3-formylcoumarins, which are important building blocks for the development of novel heterocyclic compounds. These compounds may find applications in various fields, such as pharmaceuticals, dyes, and pigments.
Used in Heterocyclic Chemistry:
This coumarin derivative is employed in the preparation of chromeno[4,3-b]quinolin-6-one, a tricyclic compound with potential applications in the field of heterocyclic chemistry. The unique structure of 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE may lead to the development of new drugs with novel mechanisms of action or the creation of new materials with specific properties.

InChI:InChI=1/C10H5ClO3/c11-9-6-3-1-2-4-8(6)14-10(13)7(9)5-12/h1-5H

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 2650-14-8 3-bromo-4-hydroxycoumarin 
• 35756-54-8 malonic acid monophenyl ester 
• 607-71-6 4-methyl-2H-chromen-2-one 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 

Downstream Products

• 154417-83-1 4-(N-allylanilino)-3-formyl-2(2H)-chromenone 
• 154417-78-4 6-(N-allylbenzylamino)-3-formyl[1]benzopyran-2(2H)-one 
• 154417-80-8 4--3-formyl-2(2H)-chromenone 
• 154417-79-5 4--3-formyl-2(2H)-chromenone 
• 136806-14-9 3-<(2-Aminophenylimino)methyl>-4-chlorcumarin 
• 100747-62-4 10-Methyl-6H-<1>benzopyrano<4,3-b>chinolin-6-on 
• 677737-41-6 4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin 

Relevant academic research and scientific papers

Synthesis, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives and related hydrazide-hydrazones

A new convenient method for preparation of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–g and coumarin containing hydrazide-hydrazone analogues 4a–e was presented. The antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and cytotoxicity against the human embryonic kidney cell line HEK-293 were tested in vitro. All compounds demonstrated significant minimum inhibitory concentrations (MIC) ranging 0.28–1.69?μM, which were comparable to those of isoniazid. The cytotoxicity (IC50?>?200?μM) to the “normal cell” model HEK-293T exhibited by 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–e, was noticeably milder compared to that of their hydrazone analogues 4a–e (IC50 33–403?μM). Molecular docking studies on compounds 4a–e and 5b–g were also carried out to investigate their binding to the 2-trans-enoyl-ACP reductase (InhA) enzyme involved in M. tuberculosis cell wall biogenesis. The binding model suggested one or more hydrogen bonding and/or arene-H or arene-arene interactions between hydrazones or pyrazole-fused coumarin derivatives and InhA enzyme for all synthesized compounds.

Design, synthesis and biological evaluation of novel benzo-α-pyrone containing piperazine derivatives as potential BRAFV600Einhibitors

The increasingly acquired resistance to vemurafenib and side effects of known inhibitors motivate the search for new and more effective anti-melanoma drugs. In this Letter, virtual screening and scaffold growth were combined together to achieve new molecu

Metal- and Catalyst-Free One-Pot Cascade Coupling of α-Enolic Dithioesters with in situ Generated 4-Chloro-3-formylcoumarin: Access to Thioxothiopyrano[3,2-c]chromen-5(2H)-ones

An efficient and viable one-pot protocol for the synthesis of a specific class of 2-thioxothiopyrano[3,2-c] chromen-5(2H)-ones has been devised by the cross-coupling of 4-hydroxycoumarin and α-enolic dithioesters under metal- and additive-free conditions in open air. The reaction proceeds via in situ generation of 4-chloro-3-formylcoumarin followed by consecutive Michael-type addition/intramolecular cyclization/ elimination cascade, enabling the creation of thiopyran-2-thione ring over coumarin framework through successive formation of C?C and C?S bonds. Remarkably, the benign conditions, atom-economy, and quantifying forbearance of a wide horizon of functional groups are added characteristics to this strategy. (Figure presented.).

In vitro and in silico evaluation of chromene based aroyl hydrazones as anticonvulsant agents

Series of aroyl hydrazones of 2H-chromene and coumarin carbaldehydes were synthesized and evaluated for their anticonvulsant activity and neurotoxicity. Further docking study on gamma-aminobutyric acid receptor was performed to elucidate their mechanisms of action. The highest protection was demonstrated by 2-furyl substituted 2H-chromene 8b in the maximal electroshock test (ED50 = 12.51 mg kg?1, PI MES > 23.98) and the subcutaneous pentylenetetrazole tests (ED50 = 127.10 mg kg?1). Furyl-substituted derivative 4b (ED50 = 68.66 mg kg?1) was the most active in the maximal electroshock test while methoxyphenyl-substituted derivate 4c was the most active in the 6-Hz test (ED50 = 94.34 mg kg?1). None of the compounds displayed neurotoxicity in the rota-rod test. In silico assessment of their blood-brain barrier permeability indicated them as central nervous system active agents. The results suggest that coumarin/2H-chromene aroyl hydrazones scaffold deserve further evaluation in models of epilepsy and derivatization.

Spectroscopic, invitro antibacterial, and antifungal studies of Co(II), Ni(II), and Cu(II) complexes with 4-chloro-3-coumarinaldehyde Schiff bases

A series of metal complexes ML2 2H2O [M = Co(II), Ni(II), and Cu(II)] have been synthesized with Schiff bases derived from 3-substituted-4-amino-5-mercapto-1,2,4-triazole and 4-chloro-3-coumarinaldehyde. The structures of these metal complexes have been proposed from elemental analyses, spectral (IR, UV-Vis, FAB-mass, ESR, and fluorescence), magnetic, and thermal studies. Low molar conductance values in DMF indicate that the metal complexes are non-electrolytes. Cyclic voltammetric studies suggested that the Ni(II) and Cu(II) complexes are single-electron transfer quasi-reversible. The Schiff bases and their metal complexes have been screened for invitro antibacterial (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Salmonella typhi) and antifungal activities (Candida albicans, Cladosporium, and Aspergillus niger) by the minimum inhibitory concentration method. The Schiff base I and its Co(II) and Ni(II) complexes exhibit DNA cleavage activity on isolated DNA of S. aureus and A. niger.

Synthesis of some novel spiro substituted pyrido[2,3-c]coumarins by exploring ‘tertiary amino effect’ reaction strategy

Some novel spiro substituted pyrido[2,3-c]coumarin derivatives were synthesized from 4-hydroxycoumarin by exploring ‘tertiary amino effect’ reaction strategy.

One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties

Two new pyranocoumarins were synthesized via one-pot, microwave-assisted pseudo multicomponent condensations of coumarin and 4-methylquinoline to investigate their molecular switching properties. Both are light-sensitive and have a distinct change of color upon UV irradiation. The reaction can be reverted by treating the photogenerated products with imidazoline-functionalized magnetic nanoparticles, which can be swiftly recycled with an external permanent magnet.

Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold

This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculo

A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

Thermolysis of a coumarin trichloroacetimidate yields a single rearrangement product. The proposed mechanism is a pseudopericyclic allowed (Woodward-Hoffman forbidden) [3,5]-sigmatropic rearrangement to form the corresponding amide followed by a sigmatropic [1,5]-hydrogen migration. Transition state calculations at the B3LYP/6-31G(d,p) level support this mechanism and suggest the selectivity is influenced by the stability of the intermediates.

Synthesis and structure of Schiff bases derived from 3-formyl-4- hydroxycoumarin and diamines

The mono- and diimine products from the condensation of 3-formyl-4-hydroxycoumarin and various diamines were synthesized. It was shown by 1H NMR and mass spectrometry that the obtained compounds in DMSO-d6 solution and in gas phase exist in the E- and Z-keto-enamine forms.