38464-20-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-nitrocoumarin is used as a key intermediate in the synthesis of new 4-heteroarylamino coumarin derivatives. These derivatives contain nitrogen and sulfur as heteroatoms, which can enhance their biological activities and make them potential candidates for pharmaceutical applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-chloro-3-nitrocoumarin serves as a versatile building block for the development of various organic compounds with diverse structures and functionalities. Its unique substitution pattern allows for further chemical modifications, enabling the creation of a wide range of molecules with potential applications in different industries.
Used in Antimicrobial Applications:
4-Chloro-3-nitrocoumarin is also utilized in the development of new antimicrobial agents. The synthesis of 4-heteroarylamino coumarin derivatives that contain nitrogen and sulfur as heteroatoms has shown promising antimicrobial activity against various pathogens. This makes 4-chloro-3-nitrocoumarin an important compound in the ongoing search for new and effective antimicrobial agents to combat drug-resistant infections.

InChI:InChI=1/C9H4ClNO4/c10-7-5-3-1-2-4-6(5)15-9(12)8(7)11(13)14/h1-4H

Upstream product

• 20261-31-8 4-hydroxy-3-nitrocoumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 108-95-2 phenol 

Downstream Products

• 50527-34-9 4-morpholin-4-yl-3-nitro-chromen-2-one 
• 88353-24-6 4-[(4-methylphenyl)amino]-3-nitro-2H-chromen-2-one 
• 88353-25-7 4-(4-methoxyphenylamino)-3-nitrocoumarin 
• 132067-77-7 3-nitro-4-(o-carboxyphenylthio)coumarin 
• 88353-23-5 4-bis(2-chloroethylamino)-3-nitrocoumarin 
• 88369-11-3 3-nitro-4-(benzylthio)coumarin 
• 88369-12-4 3,4-di-S-benzylcoumarin 
• 75908-14-4 6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one 
• 87236-30-4 4-Allylamino-3-nitrocoumarin 
• 87236-32-6 4-Cyclopentylamino-3-nitrocoumarin 
• 78795-04-7 N-(3-nitrocoumarin-4-yl)glycine 
• 88353-26-8 4-(4-acetylaminophenylamino)-3-nitrocoumarin 
• 22408-61-3 4-chloro-2-oxo-2H-[1]benzopyran-3-carbonitrile 
• 88353-31-5 4-chloro-3-benzylthiocoumarin 

Relevant academic research and scientific papers

Synthesis, in vitro cytotoxicity activity against the human cervix carcinoma cell line and in silico computational predictions of new 4-arylamino-3-nitrocoumarin analogues

A new series of 4-arylamino-3-nitrocoumarin analogues (4–18) have been synthesized and characterized by sophisticated spectroscopic techniques (1H NMR, 13C NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 μM). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 μM. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds.

Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives

A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.

A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens

Due to the confirmed antimicrobial activity of both natural and synthetic coumarin derivatives, the present study was envisaged to provide further insight into the antimicrobial potential of coumarins through the screening of a designed library of nine 4-(alkylamino)-3-nitrocoumarins against a panel of 24 laboratory strains and resistant (isolates) bacterial and fungal pathogens. All compounds showed some degree of strain-selective activity that in some cases was very pronounced, reaching the value of 0.04 nmol mL-1 (i.e., 12 ng mL-1) for the minimal inhibitory concentration against Candida albicans. The observed activities were higher against Gram-negative strains, among which the most susceptible strain, among both ATCC strains and clinical isolates, was Salmonella enterica subsp. enterica serovar Enteritidis. These results indicate to a high potential of these coumarins as antimicrobials for the treatment of gastrointestinal and other infections caused by highly resistant microbial strains. Finally, a multivariate statistical analysis of the herein obtained and previous results on the antimicrobial activity of related selected coumarins was performed to allow an easier structure-activity discussion.

A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens

Abstract: Due to a confirmed antimicrobial activity of both natural and synthetic coumarin derivatives, the present study was envisaged to provide a further insight into the antimicrobial potential of coumarins through a screening of a designed library of nine 4-(alkylamino)-3-nitrocoumarins against a panel of 24 laboratory strains and resistant (isolates) bacterial and fungal pathogens. All compounds showed some degree of strain-selective activity, that was, in some cases, very pronounced, reaching the value of 0.04 nmol/ml (i.e. 12 ng/ml) for the minimal inhibitory concentration against Candida albicans. The observed activity was higher against Gram-negative strains, among which the most susceptible strain, among both ATCC strains and clinical isolates, was Salmonella enteritidis. These results point out to a high potential of these coumarins as antimicrobials for the treatment of gastrointestinal and other infections caused by highly resistant microbial strains. Finally, a multivariate statistical analysis of the herein obtained and previous results on the antimicrobial activity of related selected coumarins was performed to allow an easier structure-activity discussion.

Could X-ray analysis explain for the differing antimicrobial and antioxidant activity of two 2-arylamino-3-nitro-coumarins?

X-Ray analyses of 4-(naphthalen-1-ylamino)- 3-nitro-chromen-2-one and 3-nitro-4-phenylamino-chromen- 2-one showed that thementioned compounds crystallize in the space groups P1- (triclinic crystal system; unit cell parameters: a = 8.087(2) ?, b = 9.241(3)

Synthesis and antimicrobial activity of new 4-heteroarylamino coumarin derivatives containing nitrogen and sulfur as heteroatoms

Synthesis, spectral analysis and bioactivity of new coumarin derivatives are described in this paper. Eight new coumarin derivatives were synthesized in moderate to good yields by condensation of 4-chloro-3-nitrocoumarin and the corresponding heteroarylam

A New approach to pyrrolocoumarin derivatives by palladium-Catalyzed reactions: Expedient construction of polycyclic lamellarin scaffold

A new and efficient protocol for straightforward synthesis of chromeno[3,4-b]pyrrol-4(3H)-one derivatives by palladium-catalyzed sequential coupling/cyclization reactions has been developed. The key strategy relies on creation of pyrrole ring through pall

Synthesis and reactions of some 4-heteroaryl-3-nitrocoumarins

By the action of 2-aminothiazole, 2-aminopyridines, and 2-aminopyrimidines, respectively, on 4-chloro-3-nitrocoumarin (3) the corresponding 4-heteroarylamino-3-nitrocoumarins 5-7 have been isolated in very good yields. Reactions of coumarins 6 and 7 with either aqueous tetrabutylammonium bisulfate/sodium hydroxide in a two phase system or 5% aqueous sodium hydroxide have been studied.

Reactions of Nitrophenols with Phosphorus Oxychloride in Dimethylformamide

A rapid and simple method for the replacement of hydroxyl group of nitrophenols and related compounds by chlorine using phosphorus oxychloride in dimethylformamide at ambient temperature is described.