15485-80-0

Basic information

• Product Name: 4H-1-BENZOPYRAN-4-ONE
• Synonyms: 7-Hydroxy-4’-nitroisoflavone
• CAS NO: 15485-80-0
• Molecular Formula: C₁₅H₉NO₅
• Molecular Weight: 283.24
• Mol File: 15485-80-0.mol

Chemical Properties

• Melting Point: 290-292℃
• Boiling Point: 530.788 °C at 760 mmHg
• Flash Point: 274.811 °C
• Appearance: Pale yellow/Powder
• Density: 1.494 g/cm³
• Vapor Pressure: 6.98E-12mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: 2-8°C
• PKA: 6.68±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4H-1-BENZOPYRAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-BENZOPYRAN-4-ONE(15485-80-0)
• EPA Substance Registry System: 4H-1-BENZOPYRAN-4-ONE(15485-80-0)

Safety Data

• Hazardous Substances Data: 15485-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4H-1-BENZOPYRAN-4-ONE is used as a synthetic intermediate for the production of isoflavones, which are a class of naturally occurring compounds with diverse biological activities. These isoflavones have been found to possess potential health benefits, including antioxidant, anti-inflammatory, and estrogenic properties.
Used in Synthesis of Daidzein:
4H-1-BENZOPYRAN-4-ONE is utilized in the synthesis of daidzin, a naturally occurring isoflavone found in soybeans. Daidzein has been studied for its potential health benefits, such as its antioxidant, anti-inflammatory, and anticancer properties.
Used in Synthesis of Flavone Amide Derivatives:
4H-1-BENZOPYRAN-4-ONE is also used as a starting material in the synthesis of flavone amide derivatives. These compounds have been investigated for their potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C15H9NO5/c17-11-5-6-12-14(7-11)21-8-13(15(12)18)9-1-3-10(4-2-9)16(19)20/h1-8,17H

Upstream product

• 137522-86-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid 
• 15485-63-9 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone 
• 122-51-0 orthoformic acid triethyl ester 
• 137522-88-4 7-Formyloxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 104-03-0 4-nitrobenzeneacetic acid 
• 108-46-3 recorcinol 
• 555-21-5 4-Nitrophenylacetonitrile 
• 15485-74-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 19816-54-7 7-methoxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 77316-78-0 7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one 
• 67523-11-9 4-[4-(4-nitro-phenyl)-isoxazol-5-yl]-benzene-1,3-diol 
• 934710-77-7 7-hydroxy-3-(4-nitrophenyl)-4-oxo-4H-1-benzopyran-8-carboxaldehyde 
• 67363-67-1 3-(p-nitrophenyl)-4,7-dihydroxycoumarin 
• 67363-66-0 2-Imino-3-(4-nitro-phenyl)-2H-chromene-4,7-diol 
• 67363-61-5 3-(2,4-Dihydroxy-phenyl)-2-(4-nitro-phenyl)-3-oxo-propionitrile 
• 486-66-8 daidzein 
• 3682-01-7 daidzein diacetate 
• 1426687-89-9 N-(4-(7-(3-hydroxy-3-methylbut-1-ynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-21-2 N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-28-9 N-(4-(7-((2-tert-butoxypyridin-4-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-25-6 N-(4-(4-oxo-7-((2-oxo-1,2-dihydropyridin-4-yl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide 

Relevant articles and documents

The synthesis and anti-inflammatory evaluation of 1,2,3-triazole linked isoflavone benzodiazepine hybrids

Copper catalyzed azide-alkyne cycloaddition was used for the first time to access a small series of eight novel 1,2,3-triazole linked isoflavone benzodiazepine hybrids. As part of this work, a previously unreported alkyne substituted pyrrolo[1,4]benzodiaz

Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities

Our group has previously reported a series of isoflavone derivatives with antidyslipidemic activity. With this background, a series of isoflavone analogs of GW4064 were designed, synthesized and evaluated the lipid-lowering activity of analogs. As a result, most of compounds significantly reduced the lipid accumulation in 3T3-L1 adipocytes and four of them (10a, 11, 15c and 15d) showed stronger inhibitory than GW4064. The most potent compound 15d exhibited promising agonistic activity for FXR in a cell-based luciferase reporter assay. Meanwhile, 15d up-regulated FXR, SHP and BSEP gene expression and down-regulated the mRNA expression of lipogenesis gene SREBP-1c. Besides, an improved safety profile of 15d was also observed in a HepG2 cytotoxicity assay compared with GW4064. The obtained biological results were further confirmed by a molecular docking study showing that 15d fitted well in the binding pocket of FXR and interacted with some key residues simultaneously.

Novel isoflavone derivative, preparation method therefor and medicinal use of novel isoflavone derivative

The invention relates to the field of pharmaceutical chemistry, relates to an isoflavone derivative, a preparation method therefor and medicinal use of the novel isoflavone derivative and particularlyrelates to isoflavone derivatives represented by a general formula (I) shown in the description, preparation methods therefor, pharmaceutical compositions containing these compounds and medicinal useof the isoflavone derivatives and the pharmaceutical compositions, particularly use of drugs for preventing or treating hyperlipidemia, type II diabetes, atherosclerosis and non-alcoholic fatty hepatitis.

Isoflavone amide derivatives, their preparation method and medical use

The invention belongs to the field of medicinal chemistry, and relates to derivatives of isoflavones amides, as well as a preparation method and medical application of derivatives, in particular to the derivatives of the isoflavones amides with the general formula of (I) shown as the specification, the preparation method and the medical application of the derivatives, particularly the application of the derivatives of the isoflavones amides serving as medicaments for preventing or treating hyperlipemia, adiposis or type-II diabetes.

Synthesis and biological evaluation of isoflavone amide derivatives with antihyperlipidemic and preadipocyte antiproliferative activities

A series of isoflavone amides were designed with isoflavone in place of the scaffold of 2-arylbenzoxazole as cholesterol ester transfer protein (CETP) inhibitors. Twelve new compounds were synthesized, and their inhibitory activities of CETP and preadipocyte proliferation were assayed. The hypolipidemic potency of the most effective compound HY-2c was further tested in vivo by hamster. The results indicate that HY-2c exhibited favorable antihyperlipidemic and preadipocyte antiproliferative activities.

Novel daidzein analogs and their in vitro anti-influenza activities

A series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti-influenza activity, in vitro, against H1N1 Tamiflu-resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g were most promising, and they demonstrated better activities and selectivities comparable to those the reference ribarivin, a nucleoside antiviral agent. 3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) displayed the best inhibitory activity (EC50, 29.0 μM) and selectivity index (SI>10.3). Analysis of the structure￡activity relationships (SAR) indicated that both the non-naturally-occurring Br-substituted B-ring and appropriate CHO and OH groups on the A-ring might be critical for the activity and selectivity against H1N1 TR influenza viruses.

Enzymatic studies of isoflavonoids as selective and potent inhibitors of human leukocyte 5-lipo-oxygenase

Continuing our search to find more potent and selective 5-LOX inhibitors, we present now the enzymatic evaluation of seventeen isoflavones (IR) and nine isoflavans (HIR), and their in vitro and in cellulo potency against human leukocyte 5-LOX. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Of these three, IR-2 (6,7-dihydroxy-4-methoxy-isoflavone, known as texasin) was the most selective 5-LOX inhibitor, with over 80-fold potency difference compared with other isozymes; Steered Molecular Dynamics (SMD) studies supported these findings. The presence of the catechol group on ring A (6,7-dihydroxy versus 7,8-dihydroxy) correlated with their biological activity, but the reduction of ring C, converting the isoflavones to isoflavans, and the substituent positions on ring B did not affect their potency against 5-LOX. Two of the most potent/selective inhibitors (HIR-303 and HIR-309) were reductive inhibitors and were potent against 5-LOX in human whole blood, indicating that isoflavans can be potent and selective inhibitors against human leukocyte 5-LOX in vitro and in cellulo. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Docking and steered molecular dynamics were performed to determinate the structure-activity relationship.

In vitro study of isoflavones and isoflavans as potent inhibitors of human 12- and 15-lipoxygenases

In this study, we have investigated 16 isoflavone and isoflavan derivatives as potential inhibitors of human lipoxygenase (platelet 12-lipoxygenase, reticulocyte 15-lipoxygenase-1, and epithelial 15-lipoxygenase-2). The flavonoid baicalein, a known lipoxygenase inhibitor, was used as positive control. Four compounds, 6,7-dihydroxy-3′-chloroisoflavone (1c), 7-hydroxy-8-methyl-4′-chloroisoflavan (5a), 7,8-dihydroxy-4′-methylisoflavan (5b), and 7,8-dihydroxy-3′-methylisoflavan (5c), were effective inhibitors of 12-lipoxygenases and 15-lipoxygenase-1 with IC50's i values in the range of 0.3-3 μm.

COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH

The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

Synthesis of daidzin analogues as potential agents for alcohol abuse

Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3′ and 4′ positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4′-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3′-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4′,7-disubstituted isoflavone. The 4′-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH 2)n-OH with 2≤n ≤6, -(CH2) n-COOH with 5≤n ≤10, or -(CH2)n-NH 2 with n ≥4.