3163-07-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitroresorcinol is used as a reagent for the synthesis of Deguelin (D229205), a compound that demonstrates potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers, making 4-Nitroresorcinol an essential component in the development of cancer-fighting drugs.

InChI:InChI=1/C6H5NO4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H

Upstream product

• 136-36-7 benzoate d'hydroxy-3 phenyle 
• 698-31-7 4-nitroso-1,3-benzenediol 
• 5131-58-8 2,4-diaminonitrobenzene 
• 13722-96-8 2,4-dihydroxy-5-nitrobenzoic acid 
• 108-46-3 recorcinol 
• 110-46-3 isopentyl nitrite 
• 108-58-7 Resorcinol diacetate 
• 13722-95-7 4-hydroxy-5-nitrosalicylate 
• 89-86-1 4-hydroxysalicylic acid 
• 7732-18-5 water 
• 98-95-3 nitrobenzene 
• 200421-95-0 5-n-pentadecyl-2-nitrophenol 
• 446-36-6 5-fluoro-2-nitrophenol 
• 825-41-2 3-chloro-4-nitroaniline 

Downstream Products

• 103204-43-9 1-(2,6-dihydroxy-3-nitro-phenyl)-butan-1-one 
• 103863-28-1 4-nitro-2-phenylazo-resorcinol 
• 103859-57-0 4-nitro-6-phenylazo-resorcinol 
• 693782-43-3 2,4-dichloro-6-nitro-resorcinol 
• 98141-37-8 4-chloro-6-nitro-resorcinol 
• 101606-04-6 4-nitro-2,6-bis-phenylazo-resorcinol 
• 13066-95-0 4-aminoresorcinol 
• 726121-37-5 2,4-dihydroxy-5-nitro-benzenesulfonic acid 
• 875235-16-8 4-bromo-6-nitro-resorcinol 
• 484653-20-5 2,4-dibromo-6-nitro-resorcinol 
• 5078-07-9 6-hydroxy-2-methylbenzoxazole 
• 25205-34-9 2,6-dihydroxy-3-nitroacetophenone 
• 3328-77-6 1-(2,4-dihydroxy-5-nitrophenyl)ethanone 
• 103261-93-4 (3-acetoxy-4-nitro-phenyl) acetate 

Relevant academic research and scientific papers

Palladium-catalyzed arylation of 2H-chromene: A new entry to pyrano[2,3-c]carbazoles

Pyrano[2,3-c]carbazoles which are biologically valuable and synthetically challenging frameworks are synthesized in high yields over five steps from commercially available resorcinol. Palladium-catalyzed arylation remains a key step in this novel strategy. The versatility of this protocol has been demonstrated by the synthesis of naturally occurring alkaloid clauraila C and 7-methoxyglycomaurin. The anti-proliferative activity of these designed compounds (5a, 5f, and 5l) has been evaluated in a cancer cell line (MOLT-4). The molecular docking study revealed that this pyrano[2,3-c]carbazole class of molecules selectively occupies the colchicine binding site of the tubulin-polymer.

Gas-Phase UV Spectroscopy of Chemical Intermediates Produced in Solution: Oxidation Reactions of Phenylhydrazines by DDQ

In this study, we demonstrated cold gas-phase spectroscopy of chemical intermediates produced in solution. Herein, we combined an electrospray ion source with a T-shaped solution mixer for introducing chemical intermediates in solution into the gas phase. Specifically, the oxidation reaction of 2-(4-nitrophenyl)hydrazinecarboxaldehyde (NHCA) by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was initiated by mixing the methanol solutions of NHCA and DDQ in the T-shaped mixer, and the chemical species were injected into the vacuum apparatus for ultraviolet photodissociation (UVPD) spectroscopy. A cationic intermediate was strongly observed at m/z 150 in the mass spectrum, and the UVPD spectrum was observed under cold (～10 K) gas-phase conditions. The UVPD spectrum showed a strong, broad absorption at ～38,000 cm-1, accompanied by a relatively weak component at ～34,000 cm-1. These spectral patterns can be ascribed to a diazonium cation intermediate, whose existence has been predicted in a previous study. This report indicates that cold gas-phase UV spectroscopy can be a useful method for identifying the structure of chemical intermediates produced in solution.

A 7-hydroxybenzoxazinone-containing fluorescence turn-on probe for biothiols and its bioimaging applications

In this work, a novel 7-hydroxybenzoxazinone-based fluorescent probe (PBD) for the selective sensing of biothiols is reported. Upon treatment with biothiols, PBD shows a strong fluorescence enhancement (up to 70-fold) and a large Stokes shift (155 nm). Meanwhile, this probe exhibits high resistance to interference from other amino acids and competing species. PBD features good linearity ranges with a low detection limit of 14.5 nM for glutathione (GSH), 17.5 nM for cysteine (Cys), and 80.0 nM for homocysteine (Hcy), respectively. Finally, the potential utility of this probe for biothiol sensing in living HeLa cells is demonstrated.

A Michael addition-cyclization-based switch-on fluorescent chemodosimeter for cysteine and its application in live cell imaging

Based on a conjugate addition/intramolecular cyclization sequence, we designed and synthesized a fast response fluorescent probe, BTAC (benzothiazol-azacoumarin), for the discriminative detection of cysteine (Cys). The reaction of cysteine with BTAC results in the cleavage of the acrylate moiety from BTAC, thereby producing BTAC-OH, with a remarkable fluorescence enhancement at 560 nm. The probe exhibits high sensitivity and selectivity toward cysteine over homocysteine and glutathione and the detection limit reached as low as 124 nM for cysteine. The addition of Cys resulted in the color of the solution of BTAC changing from colorless to greenish yellow under the simulation of physiological conditions and BTAC could serve as a "naked-eye" indicator. The structure of BTAC was established by computational DFT (density functional theory) calculation and time dependent density functional theory (TDDFT) calculations were performed to demonstrate the electronic properties of BTAC and its product, BTAC-O-. Finally, the probe was successfully applied for the fluorescence bioimaging of cysteine owing to its photostability and low cytotoxicity.

A phenol compound green nitration method and application

The invention discloses a green nitrification method and application for a phenolic compound, belonging to the technical field of organic synthesis. The method provided by the invention comprises the following steps: with the phenolic compound as a raw material, dissolving the phenolic compound into a solvent at room temperature, adding sodium nitrite, then dropwise adding hydrogen peroxide into the obtained reaction solution, adding water-soluble metalloporphyrin at room temperature and starting reaction, carrying out nitrification reaction under stirring, then carrying out extraction by using an organic solvent, and carrying out vacuum concentration and column chromatographic separation so as to obtain a target product. The nitrification method provided by the invention has the advantages of mild reaction conditions, no need of heating, convenient operation and easy treatment of products. The green nitrification reaction is suitable for the phenolic compound.

A highly selective 7-hydroxy-3-methyl-benzoxazinone based fluorescent probe for instant detection of thiophenols in environmental samples

A new 7-hydroxy-3-methyl-benzoxazinone based fluorescent probe for thiophenols has been designed and synthesized. The probe displays highly selective and sensitive detection to thiophenols over other common analytes with instant response and remarkable large Stokes shift. It's noteworthy that biothiols, aliphatic thiols, and reducing anions do not perturb the sensing of thiophenols. The limit of detection of the probe was calculated as low as 24 nM for thiophenols. Finally, the utility of probe was illustrated by the detection of thiophenol in real environmental water samples.

Tertiary Butyl Nitrite Triggered Nitration of Phenols: Solvent- and Structure-Dependent Kinetic Study

Nitration of phenols with tertiary butyl nitrite (TBN) obeyed second-order kinetics with a first-order dependence on [TBN] and [phenol] under acid-free conditions. Reaction rates were significantly altered by a change in the dielectric constant and other physical properties of solvent. The rate of nitration increased with an increase in temperature (303-323 K) in different solvent media (acetonitrile, dichloroethane, CCl4, dimethyl formamide (DMF), and toluene). The rates of nitration (log k) could not fit into either Amis or Kirkwood plots [log k' vs. (1/D) or [(D - 1)/(2D + 1)], but the trends were better explained by the basic form of multivariate linear solvent energy relationships (MLSER) suggested by the Koppel and Palm approach on the one hand and the Kamlet and Taft approach on the other hand. These observations probably substantiate that cumulative contributions of basic solvent parameters (equilibrium as well as frictional solvent effects) and solvent-solute interactions for solvation of transition state during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups. Accordingly, the reactivity of structurally different phenols was found to follow the following sequence: p-OH > p-MeO > p-Me > H > m-Me > p-Cl > p-Br > m-Cl > p-NO2 > m-OH. The results are interpreted by Hammett's theory of linear free energy relationship. The reaction constant (Hammett's ρ) is a measure of the sensitivity of the reaction toward the electronic effects of the substituent. The rho (ρ) values obtained from the present experiments are fairly large negative values (ρ CH3) versus σ? or, Es or combined Taft's relationship. However, Charton's MLRA of the log k with polar, resonance, steric, hydrophobicity, and molar refractivity showing a very good linear relationship was obtained. It is of interest to note that when log kexp values are correlated with log kcal a perfect linearity is obtained with a correlation coefficient of unity, indicating the consonance between experimental and calculated rate constants in the present work.

Environment-friendly bionic catalytic nitration method for phenolic compound

The invention discloses an environment-friendly bionic catalytic nitration method for a phenolic compound and belongs to the technical field of organic synthesis. The method provided by the invention comprises the steps of dissolving the phenolic compound, which serves as a raw material, in a solvent at normal temperature, adding sodium nitrite into the solution, then, dropwise adding hydrogen peroxide into the reaction solution, adding metal-doped Al-MCM-41 molecular sieves into the reaction solution at normal temperature so as to start a reaction, carrying out stirring so as to carry out a nitration reaction, and then, carrying out suction filtration, organic solvent extraction, depressurized concentration and column chromatography separation, thereby obtaining a target product. According to the nitration method disclosed by the invention, the reaction conditions are mild, heating is not required, the operation is convenient, and the product is easy to treat. The nitration method is applicable to an environment-friendly bionic catalytic nitration reaction for phenolic compounds.

Regioselective nitration of phenols and phenyl ethers using aluminium nitrate on silica as a nitrating system

Silica supported aluminum nitrate (Al(NO3)3·9H2O) was found to be an excellent reagent for the nitration of phenols and phenyl ethers. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity. The present methodology evidenced a considerable enhancement in the reaction rate along with high o-selectivity, excellent yields, ease of handling and the simplicity in work up.

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel compound inhibiting Hsp 90 and to a pharmaceutical composition including same as an active ingredient. Compounds of formula 1 and formula 2 according to the present invention inhibit the accumulation of HIF-1α protein, which is an Hsp90 client protein, by suppressing Hsp90 expression, and effectively inhibit the activity of vascular endothelial growth factor (VEGF). Furthermore, said compounds have low cytotoxicity and can thus be used as an active ingredient for the treatment of diabetic retinopathy and arthritis.