113326-75-3

Upstream product

• 17422-74-1 3-Formylchromone 
• 98-95-3 nitrobenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 

Downstream Products

• 113326-77-5 3-(2,5-Diphenyl-isoxazolidin-3-yl)-chromen-4-one 
• 113326-82-2 3-(2-Phenyl-5-p-tolyl-isoxazolidin-3-yl)-chromen-4-one 
• 113355-09-2 3-(4-Oxo-4H-chromen-3-yl)-2,5-diphenyl-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 113326-79-7 3-(4-Oxo-4H-chromen-3-yl)-2-phenyl-isoxazolidine-5-carbonitrile 
• 33588-64-6 ethyl 2-(1H-indol-2-yl)acetate 
• 213273-03-1 4-oxo-2-(N-phenyl)amino-4H-chromene-3-carbaldehyde 
• 14190-78-4 ethyl 2-(3-methyl-1H-indol-2-yl)acetate 
• 1168003-64-2 2-(carboethoxymethyl)-3-ethylindole 
• 1168003-61-9 1-benzylcarbonyl-3-(2'-hydroxybenzoyl)benzo[b]indolizine 
• 1219020-15-1 3-(ethylaminomethylene)-2-(N-phenyl)-iminochroman-4-one 
• 81590-83-2 7,16-bis(2-hydroxybenzoyl)-5,14-dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecine 
• 547741-45-7 4-oxo-2-[N-(phenyl)-N-(prop-2-enyl)]amino-4H-1-benzopyran-3-carboxaldehyde 
• 547741-47-9 4-oxo-2-[N-(phenyl)-N-(3-phenylprop-2(E)-enyl)amino]-4H-1-benzopyran-3-carboxaldehyde 
• 1345096-79-8 3-(2-hydroxybenzoyl)-1-methylquinolin-2(1H)-one 

Relevant academic research and scientific papers

Intramolecular low-temperature 1,3-dipolar cycloadditions of nitrones: synthesis of chromano-heterocycles

In contrast to the reported facile intramolecular 1,3-dipolar cycloadditions of in-situ generated nitrone on heterocyclic systems, reactions of 2-(N-allyl/crotyl/cinnamyl-anilino)-3-formylchromones with N-phenyl-/methylhydroxylamine under comparable condi

Synthesis and cytotoxicity evaluation of regioisomeric substituted N-phenyl-3′-(chrom-4-one-3-yl)-isoxazolidines: Induction of apoptosis through a mitochondrial-dependent pathway

Regio- and stereoselective 1,3-dipolar cycloadditions of C-(chrom-4-one-3-yl)-N-phenylnitrones (5) with different mono-substituted, disubstituted and cyclic dipolarophiles were carried out to obtain substituted N-phenyl-3′-(chrom-4-one-3-yl)-isoxazolidines (7a-p, 10a-c and 12a-c). Some of the obtained isoxazolidines display significant cytotoxicity against several human cancer cell lines. The preliminary bioassay results revealed that compound 10c showed higher cytotoxicity than paclitaxel against the A549 cell line with an IC50 value of 0.7 μM. Compound 10c induces apoptosis through a mitochondrial-dependent pathway in human promyelocytic leukemia (HL-60) cells as revealed by induced apoptotic bodies' formation, DNA ladder, increased Sub-G0 DNA fraction and loss of mitochondrial membrane potential (ΔΨm) in HL-60 cells.

Thermal rearrangements of C-(4-Oxo-4H[1]benzopyran-3-yl)-N- phenylnitrone-a route to novel quinolino[2,3-b] chroman-12-ones

C-(4-Oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones (1a-c) undergo facile rearrangements on refluxing in benzene, yielding 2-(N-phenylamino)-4-oxo- 4H[1]-benzopyran-3-carboxaldehydes (2a-c,70%) and 3-(phenyliminomethylene)- chroman-2,4-diones (3a-c, 25%). 2a-

Chromanyl-isoxazolidines as Antibacterial agents: Synthesis, Biological Evaluation, Quantitative Structure Activity Relationship, and Molecular Docking Studies

Regio- and stereoselective 1,3-dipolar cycloadditions of C-(chrom-4-one-3-yl)-N-phenylnitrones (N) with different mono-substituted, disubstituted, and cyclic dipolarophiles were carried out to obtain substituted N-phenyl-3′-(chrom-4-one-3-yl)-isoxazolidines (1-40). All the synthesized compounds were assayed for their in vitro antibacterial activity and display significant inhibitory potential; in particular, compound 32 exhibited good inhibitory activity against Salmonella typhymurium-1 & Salmonella typhymurium-2 with minimum inhibitory concentration value of 1.56 μg/mL and also showed good potential against methicillin-resistant Staphylococcus aureus with minimum inhibitory concentration 3.12 μg/mL. Quantitative structure activity relationship investigations with stepwise multiple linear regression analysis and docking simulation studies have been performed for validation of the observed antibacterial potential of the investigated compounds for determination of the most important parameters regulating antibacterial activities.

3-Formylchromone based topoisomerase IIα inhibitors: Discovery of potent leads

Substituted 3-formylchromones were synthesized and evaluated as inhibitors of the human DNA topoisomerase IIα (hTopo-IIα) enzyme. The results of the decatenation, relaxation and DNA intercalation assays revealed that the compounds (11b, 12a, 12b, 12d, 12e, 13a and 13b) exhibited potent inhibitory activity against the hTopo-IIα enzyme, and are nonintercalating agents. These compounds also possess significant in vitro cytotoxicity (LC50 ranges from 0.5-8.6 μM) against prostate (PC-3) cancerous cell line as seen in comparison to the standard drug etoposide. To further probe the plausible mode of action of 3-formylchromone derivatives, molecular docking studies have also been carried out, which showed that the compounds under investigation fitted well in the ATP binding pocket of hTopo-IIα enzyme with good docking scores and form nonbonding interactions with the crucial residues of the catalytic site. The Royal Society of Chemistry.

Exploring α-chromonyl nitrones as 1,5-dipoles

N-Phenyl-C-chromonyl nitrones 1 and the allenoate zwitterion 2, generated by addition of phosphine to acetylenedicarboxylates, undergo a cascade reaction sequence involving an unprecedented [5+3] annulation followed by deoxygenative rearrangement leading to dihydropyridine-fused benzopyrones. Unusual electronic control by the N-substituents of 1 directs the annulation pathway, leading to two different ring-systems. Georg Thieme Verlag Stuttgart - New York.

A one-pot rearrangement of 2-(N-Alkyl-N-aryl)aminochromone-3-carbaldehyde to N-Alkyl-3-salicyloyl-2-quinolone - An antileishmanial agent

2-(N-Aryl)aminochromone-3-carbaldehyde does not show any change on heating in acetic acid, but under the same reaction conditions 2-(N-alkyl-N-aryl) aminochromone-3-carbaldehyde rearranges to 3-salicyloyl-2-quinolones, which exhibits antileishmanial activ

Study of differences in the reactivity of alkyl and aryl nitrones derived from 4-oxo-4H-1-benzopyran-3-carboxaldehyde

On hydrolysis with 70% H2SO4, aliphatic nitrones 2a-d produce the corresponding carboxylic acids 4, but aromatic nitrones 2e, f give aldehyde 1. On heating under reflux in dry MeOH, 2a-d rearrange to 3a-d but aromatic nitrones 2e, f

Rearrangements of N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1- benzopyran-3-carboxaldehyde - A solvent-dependent process

C-(4-Oxo-4H-1-benzopyran-3-yl)-N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1-benzopyran-3-carboxaldehyde, rearrange to 2-alkyl-/aryl-amino-3- formylchromone and/or 3-(alkyl-/aryl-aminomethylene)chroman-2,4-dione depending upon the reaction medium. 3-(Alkylaminomethylene)chroman-2,4-dione has been utilized in the synthesis of 1-benzopyrano[3,4-d]isoxazole-4-one.

One-pot Synthesis of 2-alkyl/arylamino-4-oxo-4H-1-benzopyran-3-carboxaldehyde from 4-oxo-4H-1-benzopyran-3-carboxaldehyde

Zn/NH4Cl - Mediated reactions of aldehyde 1 with nitro compounds 2 afford 2-(N-alkyl/arylamino)-3-formylchromones 4, which on heating with 70 percent H2SO4 produces 9a-d and 11e-h from 4a-d and 4e-h, respectively.