42059-55-2

Usage

Uses

Used in Pharmaceutical Industry:
4H-1-Benzopyran-3-carboxaldehyde, 7-hydroxy-4-oxois used as a pharmaceutical compound for its antioxidant, anti-inflammatory, and antimicrobial properties. Its potential pharmacological activities make it a promising candidate for the development of new drugs and therapies.
Used in Organic Synthesis:
4H-1-Benzopyran-3-carboxaldehyde, 7-hydroxy-4-oxois used as a building block in organic synthesis. Its chemical properties make it suitable for the development of new pharmaceuticals and other chemical compounds.
Used in Health and Medicine:
4H-1-Benzopyran-3-carboxaldehyde, 7-hydroxy-4-oxois used in the fields of health and medicine due to its potential pharmacological activities. Its antioxidant, anti-inflammatory, and antimicrobial properties make it a valuable compound for research and development in these areas.

Upstream product

• 108-46-3 recorcinol 
• 42059-49-4 7-Acetoxychromone-3-carboxaldehyde 
• 42059-48-3 acetic acid 4-acetyl-3-hydroxyphenyl ester 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 42059-56-3 7-methoxy-3-formylchromone 
• 57811-90-2 C₉H₉BF₂O₃ 

Downstream Products

• 1146066-33-2 C₁₈H₁₀Cl₂O₄ 
• 1146066-32-1 C₁₉H₁₄O₅ 
• 1146066-34-3 C₁₈H₁₀Cl₂O₄ 
• 1146066-35-4 C₁₈H₁₁NO₆ 
• 1253693-23-0 2-(7-hydroxy-4-oxo-4H-1-benzopyran-3-yl)-7-hydroxy-4-(N-cyclohexylimino)pyrano[3,4-b]-1-benzopyran-10-one 
• 1448640-50-3 5-(3,5-dibromo-2,4-dihydroxybenzoyl)-2-oxo-2H-1-(pyridin-2-yl)pyridine-3-carbonitrile 
• 1448640-51-4 2-(3,5-dibromo-2,4-dihydroxybenzoyl)pyrido[1,2-a]benzimidazole-4-carbonitrile 
• 1448640-52-5 6-[(3,5-dibromo-2,4-dihydroxyphenyl)carbonyl]-1,3-dimethyl-1H,2H,3H,4H-pyrido[2,3-d]pyrimidine-2,4-dione 
• 1146066-37-6 C₂₄H₁₆N₂O₃ 
• 1146066-38-7 C₂₄H₁₅ClN₂O₃ 
• 1146066-39-8 C₂₄H₁₅BrN₂O₃ 
• 1146066-41-2 C₂₅H₁₈N₂O₃ 
• 1146066-44-5 C₂₅H₁₈N₂O₄ 
• 1146066-46-7 C₂₄H₁₄Cl₂N₂O₃ 

Relevant academic research and scientific papers

Synthesis of O-β-D-glucopyranosides of 7-hydroxy-3-(imidazol-2-yl)-4H- chromen-4-ones

The 7-hydroxy-3-formyl-4H-chromen-4-one 1 reacted with various cyclic 1,2-dicarbonyl compounds in the presence of ammonium acetate to furnish 7-hydroxy-3-([4,5-fused] imidazol-2-yl)-4H-chromen-4-ones 2a-f, which on glucosylation with -acetobromoglucose af

Antimicrobial/antioxidant activity and POM analyses of novel 7-o-β-D-glucopyranosyloxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones

A series of 7-o-β-D-glucopyranosyloxy-3-(4,5-disubstituted imidazol-2-yl)-4H-chromen-4-ones 4 were synthesized and tested for in vitro antibacterial/antifungal and antioxidant activity. The synthesized compounds o-β-D-glucoside of 7-hydroxyl-3-imidazolyl-

Synthesis and DNA Binding Affinity of Some New 7-Hydroxy-3-Carbaldehyde Chromones

Two novel ligands, 7-methoxy chromone-3-carbaldehyde-salicylyl hydrazone and 7-hydroxy chromone-3-carbaldehyde-salicylyl hydrazone, were prepared by resorcinol their respective Eu (III) complexes had been synthesized and characterized on the base of elemental analyses, molar conductivities, IR spectra, mass spectra, UV-Vis spectra, and fluorescence studies the interactions of the Eu (III) complexes and their ligands with calf-thymus DNA were investigated, which were found that both two ligands and their rare earth complexes could strongly bind with calf-thymus DNA via an intercalation mechanism.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

Design, synthesis and anti-TMV activities of novel chromone derivatives containing dithioacetal moiety

Thirty-five novel chromone derivatives containing dithioacetal moiety were designed, synthesized, and their anti-TMV activities were evaluated through half-leaf method. The results showed compound c23 illustrates highly curative, protective and inactivating activities against TMV at 500 mg/L, with the values of 68.8%, 58.8%, 86.0% respectively, which were superior to that of Ribavirin (42.3%, 49.8%, 68.4%, respectively) and similar to that of Ningnanmycin (59.4%, 52.4%, 88.4%, respectively). The EC50 value of inactivating activities of compound c23 is 9.3 mg/L, which was better than that of Ribavirin (135.2 mg/L), and equivalent to that of Ningnanmycin (8.8 mg/L). Furthermore, compound c23 can destroy the integrity of TMV-CP, resulting in reduced infectivity of TMV. Meanwhile, compound c23 can combine with TMV protein coat and hydrolyze TMV protein coat to impact the process of self-assembling of TMV, with the association constant (Kd) 4.5 mg/L. This finding suggests that chromone derivatives containing dithioacetal moiety can be used as new antiviral agent.

Novel copper(II), cobalt(II) and nickel(II) complexes with 5-(4-oxo-4H-chromen-3-yl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide: Synthesis, structure, spectroscopic studies

A series of novel organic ligands, 5-(4-oxo-4H-chromen-3-yl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide, which are the tautomeric forms of 2-oxo-2-(arylamino)-(2E)-2- [(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-methyledene]ethanethioic acid hydrazides, have been synthesized from 3-formylchromone and oxamic acid thiohydrazides. Copper(II), cobalt(II) and nickel(II) complexes with 2-oxo-2-(arylamino)-(2E)-2-[(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)methyledene]ethanethioic acid hydrazides have been synthesized by the interaction of corresponding organic ligands with MCl2 (M = Cu, Co, Ni). The crystal structure of a copper(II) complex with 5-(4-oxo-4H-chromen-3-yl)-N-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide has been solved by a single-crystal X-ray diffraction method. The copper(II) ions in complex molecule are coordinated by aldimine nitrogen atom, thiolate sulfur atom and the oxygen atom the pyrone ring keto-group as well as two bridged chloride anions in a distorted triangular bipyramidal geometry. The electrochemical investigations of synthesized ligands and complexes have been performed by cyclic voltammetry technique.

Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives

A novel series of chromone-isatin derivatives 6a–6p were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12–16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 6j (IC50 = 3.18 ± 0.12 μM) with a hydroxyl group at the 7-position of chromone and a 4-bromobenzyl group at the N1-positions of isatin, was found to be the most active compound among the series. Furthermore, molecular docking study was performed to help understand binding interactions of the most active analogs with α-glucosidase enzyme. These results indicated that this class of compounds had potential for the development of anti-diabetic agents.

Synthesis, biological evaluation and molecular docking studies of chromone hydrazone derivatives as α-glucosidase inhibitors

A series of chromone hydrazone derivatives 4a–4p have been synthesized, characterized by 1H NMR and 13C NMR and evaluated for their?in?vitro α-glucosidase inhibitory activity. Out of these tested compounds, six (4a, 4b, 4d, 4j, 4o and 4p) displayed potent α-glucosidase inhibitory activity with IC50 values in the range of 20.1?±?0.19?μM to 45.7?±?0.23?μM, as compared to the standard drug acarbose (IC50?=?817.38?±?6.27?μM). Among this series, compound 4d (IC50?=?20.1?±?0.19?μM) with 4-sulfonamide substitution at phenyl part of hydrazide was found to be the most active compound. Lineweaver-Burk plot analysis indicated that compound 4d is a non-competitive inhibitor of α-glucosidase. The binding interactions of the most active analogs were confirmed through molecular docking studies. Docking studies showed 4d are interacting with the residues Glu-276, Asp-214, Asp-349 and Arg-439 through hydrogen bonds, arene-anion and arene-cation interactions. In summary, our studies shown that these chromone hydrazone derivatives are a new class of α-glucosidase inhibitors.

Inhibition of Alzheimer's BACE-1 by 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates

Alzheimer's disease is the most common cause of dementia in the elderly, and no disease-modifying therapy is yet available for this devastating pathology. Deposition of different physicochemical forms of amyloid-β peptides is a critical phase in the patho

Studies on the chemical behavior of the novel 6,8-dibromo-7- hydroxychromone-3-carboxaldehyde towards some carbon nucleophilic reagents

A novel 6,8-dibromo-7-hydroxychromone-3-carboxaldehyde (4) was prepared by the Vilsemier-Haack formylation of 3,5-dibromo-2,4-dihydroxy acetophenone (3). The chemical reactivity of carboxaldehyde 4 was studied towards some carbon nucleophiles as cyclic and acyclic active methylene nucleophiles and also 1,3-C,N- and 1,3-C,C-binucleophiles as a route to achieve ring transformation to produce a variety of heterocyclic systems. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data.