15485-63-9

Basic information

• Product Name: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-NITRO-PHENYL)-ETHANONE
• Synonyms: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-NITRO-PHENYL)-ETHANONE;1-(2,4-Dihydroxy-phenyl)-2-(4-nitro-phenyl)-ethanone ,98%
• CAS NO: 15485-63-9
• Molecular Formula: C₁₄H₁₁NO₅
• Molecular Weight: 273.25
• Mol File: 15485-63-9.mol

Chemical Properties

• Melting Point: 2210°C
• Boiling Point: 523.6°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.435g/cm³
• Vapor Pressure: 1.4E-11mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-NITRO-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-NITRO-PHENYL)-ETHANONE(15485-63-9)
• EPA Substance Registry System: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-NITRO-PHENYL)-ETHANONE(15485-63-9)

Safety Data

• Hazardous Substances Data: 15485-63-9(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of p-nitropheny-–lacetonitrile with resorcinol (Hoesch reaction).

InChI:InChI=1/C14H11NO5/c16-11-5-6-12(14(18)8-11)13(17)7-9-1-3-10(4-2-9)15(19)20/h1-6,8,16,18H,7H2

Upstream product

• 555-21-5 4-Nitrophenylacetonitrile 
• 108-46-3 recorcinol 
• 104-03-0 4-nitrobenzeneacetic acid 

Downstream Products

• 77316-93-9 7-acetoxy-2-methyl-3-(4-nitro-phenyl)-chromen-4-one 
• 15485-74-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 32256-26-1 7-hydroxy-3-(4-nitro-phenyl)-2-phenyl-chromen-4-one 
• 15485-80-0 7-hydroxy-3-(4-nitrophenyl)-4H-chromen-4-one 
• 57272-98-7 2-hydroxy-4-methoxy-4'-nitro-deoxybenzoin 
• 137522-88-4 7-Formyloxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 77316-78-0 7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one 
• 640275-83-8 7-O-ethoxycarbonylpentyl-4'-nitroisoflavone 
• 19816-54-7 7-methoxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 137522-86-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid 
• 1155265-03-4 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone oxime 
• 1241384-60-0 1-(2-hydroxy-4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)-2-(4-nitrophenyl)ethanone 
• 934710-77-7 7-hydroxy-3-(4-nitrophenyl)-4-oxo-4H-1-benzopyran-8-carboxaldehyde 

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

Discovery and Development of Small-Molecule Inhibitors of Glycogen Synthase

The overaccumulation of glycogen appears as a hallmark in various glycogen storage diseases (GSDs), including Pompe, Cori, Andersen, and Lafora disease. Accumulating evidence suggests that suppression of glycogen accumulation represents a potential therapeutic approach for treating these GSDs. Using a fluorescence polarization assay designed to screen for inhibitors of the key glycogen synthetic enzyme, glycogen synthase (GS), we identified a substituted imidazole, (rac)-2-methoxy-4-(1-(2-(1-methylpyrrolidin-2-yl)ethyl)-4-phenyl-1H-imidazol-5-yl)phenol (H23), as a first-in-class inhibitor for yeast GS 2 (yGsy2p). Data from X-ray crystallography at 2.85 ?, as well as kinetic data, revealed that H23 bound within the uridine diphosphate glucose binding pocket of yGsy2p. The high conservation of residues between human and yeast GS in direct contact with H23 informed the development of around 500 H23 analogs. These analogs produced a structure-activity relationship profile that led to the identification of a substituted pyrazole, 4-(4-(4-hydroxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrogallol, with a 300-fold improved potency against human GS. These substituted pyrazoles possess a promising scaffold for drug development efforts targeting GS activity in GSDs associated with excess glycogen accumulation.

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.

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.

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.

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.

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.

Metronidazole-deoxybenzoin derivatives as anti-Helicobacter pylori agents with potent inhibitory activity against HPE-induced interleukin-8

A series of new metronidazole-deoxybenzoin derivatives were synthesized and evaluated for their antimicrobial activity against Helicobacter pylori. Highly selective anti-H. pylori activity was also observed in synthesized compounds. Compound 34 exhibited

Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease

Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4′-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental.

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.