14543-43-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-cyano-phenol is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with specific therapeutic properties.
Used in Dye Industry:
In the dye industry, 2-Amino-4-cyano-phenol is utilized as an intermediate for the production of various dyes. Its chemical properties contribute to the color and stability of the dyes, making it an essential component in dye manufacturing.
Used in Organic Compounds Synthesis:
2-Amino-4-cyano-phenol serves as an intermediate in the synthesis of other organic compounds, including agrochemicals and specialty chemicals. Its versatility in chemical reactions makes it a valuable building block in organic chemistry.
Used in Antioxidant Applications:
Due to its potential antioxidant properties, 2-Amino-4-cyano-phenol is being studied for its ability to protect against oxidative stress and damage in various applications, including food preservation and health supplements.
Used in Antimicrobial Applications:
2-Amino-4-cyano-phenol has also been studied for its antimicrobial properties, making it a potential candidate for use in disinfectants, sanitizers, and preservatives in various industries, including healthcare and food processing.

InChI:InChI=1/C7H6N2O/c8-4-5-1-2-7(10)6(9)3-5/h1-3,10H,9H2

Upstream product

• 3272-08-0 4-hydroxy-3-nitrobenzonitrile 
• 111318-35-5 4-acetoxy-3-nitro-benzonitrile 
• 767-00-0 4-cyanophenol 
• 16237-96-0 4-(Isopropylideneaminoxy)benzonitrile 

Downstream Products

• 93794-41-3 2-mercaptobenzo[d]oxazole-5-carbonitrile 
• 357156-63-9 N-(5-cyano-2-hydroxy-phenyl)-4-phenoxy-benzamide 
• 134997-74-3 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile 
• 476303-97-6 4-hydroxy-3-{3-[4-(pyrrolidin-1-yl-carbonyl)-3-methyl-phenyl]-propargylamino}-benzonitrile 
• 854163-79-4 2-(4-nitro-phenyl)-benzoxazole-5-carbonitrile 
• 357156-65-1 3,5-di-tert-butyl-N-(5-cyano-2-hydroxy-phenyl)-2-hydroxy-benzamide 
• 1026273-07-3 2-Bromo-N-(5-cyano-2-hydroxy-phenyl)-acetamide 
• 93794-41-3 5-cyanobenzo[d]oxazole-2-(3H)-thiazone 
• 84435-42-7 2-amino-4-amidiniumphenolate dihydrate 
• 1198296-50-2 2-amino-4-(3,4,5,6-tetrahydropyrimidinium-2-yl)phenolate hydrate 
• 182932-74-7 2-amino-4-(4,5-dihydro-1H-imidazolium-2-yl)phenolate hydrate 

Relevant academic research and scientific papers

Targeting the subpocket in xanthine oxidase: Design, synthesis, and biological evaluation of 2-[4-alkoxy-3-(1H-tetrazol-1-yl) phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives

Xanthine oxidase is an important target for the treatment of hyperuricemia, gout and other related diseases. Analysis of the high-resolution structure of xanthine oxidase with febuxostat identified the existence of a subpocket formed by the residues Leu648, Asn768, Lys771, Leu1014 and Pro1076. In this study, we designed and synthesized a series of 2-[4-alkoxy-3-(1H-tetrazol-1-yl) phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives (8a-8z) with a tetrazole group targeting this subpocket of the xanthine oxidase active site, and they were further evaluated for their inhibitory potency against xanthine oxidase in vitro. The results showed that all the tested compounds (8a-8z) exhibited an apparent xanthine oxidase inhibitory potency, with IC50 values ranging from 0.0288 μM to 0.629 μM. Among them, compound 8u emerged as the most potent xanthine oxidase inhibitor, with an IC50 value of 0.0288 μM, which was comparable to febuxostat (IC50 = 0.0236 μM). The structure-activity relationship results revealed that the hydrophobic group at the 4′-position was indispensable for the inhibitory potency in vitro against xanthine oxidase. A Lineweaver-Burk plot revealed that the representative compound 8u acted as a mixed-type inhibitor for xanthine oxidase. Furthermore, molecular modeling studies were performed to gain insights into the binding mode of 8u with xanthine oxidase and suggested that the tetrazole group of the phenyl unit was accommodated in the subpocket, as expected. Moreover, a potassium oxonate-induced hyperuricemia model in rats was chosen to further confirm the hypouricemic effect of compound 8u, and the result demonstrated that compound 8u could effectively reduce serum uric acid levels at an oral dose of 5 mg/kg. In addition, acute oral toxicity study in mice indicated that compound 8u was nontoxic and tolerated at a dose up to 2000 mg/kg. Thus, compound 8u could be a potential and efficacious agent in treatment of hyperuricemia with low toxicity.

Amidino substituted 2-aminophenols: biologically important building blocks for the amidino-functionalization of 2-substituted benzoxazoles

Unlike the closely related and widely investigated amidino-substituted benzimidazoles and benzothiazoles with a range of demonstrated biological activities, the matching benzoxazole analogues still remain a largely understudied and not systematically evaluated class of compounds. To address this challenge, we utilized the Pinner reaction to convert isomeric cyano-substituted 2-aminophenols into their amidine derivatives, which were isolated as hydrochlorides and/or zwitterions, and whose structure was confirmed by single crystal X-ray diffraction. The key step during the Pinner synthesis of the crucial carboximidate intermediates was characterized through mechanistic DFT calculations, with the obtained kinetic and thermodynamic parameters indicating full agreement with the experimental observations. The obtained amidines were subjected to a condensation reaction with aryl carboxylic acids that allowed the synthesis of a new library of 5- and 6-amidino substituted 2-arylbenzoxazoles. Their antiproliferative features against four human tumour cell lines (SW620, HepG2, CFPAC-1, HeLa) revealed sub-micromolar activities on SW620 for several cyclic amidino 2-naphthyl benzoxazoles, thus demonstrating the usefulness of the proposed synthetic strategy and promoting amidino substituted 2-aminophenols as important building blocks towards biologically active systems.

Phenazine and phenothiazine covalent triazine framework material as well as preparation method and application thereof

The invention discloses a phenazine or phenothiazine covalent triazine framework material and a preparation method and application thereof. After the reaction is finished, water and acid are used for washing, and the obtained solid product is a phenazine

Tetrazole xanthine oxidase inhibitor compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines and relates to a tetrazole xanthine oxidase inhibitor compound as well as a preparation method and application thereof. The invention providesa tetrazole xanthine oxidase inhibitor compound shown as a general formula I or a pharmaceutically acceptable salt, an isomer, a polymorphic substance and a medicinal solvate and further provides anintermediate for preparing the tetrazole xanthine oxidase inhibitor compound or the pharmaceutically acceptable salt, and a structure of the intermediate is shown as a general formula II, III or IV, wherein R is described as claims and a description.

Compounds with xanthine oxidase inhibition activity, and preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to compounds with xanthine oxidase inhibition activity, and a preparation method and an application thereof. The invention provides the compounds with xanthine oxidase inhibition activity, represented by general formula I, or pharmaceutically acceptable salts, isomers, polymorphs and medical solvates thereof, and further provides an intermediate for preparing the compounds with xanthine oxidase inhibition activity, or the pharmaceutically acceptable salts thereof. The structure of the intermediate is represented by generalformula II or III shown in the description; and R in the general formulas is as defined in claims and the description.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

Preparation method of benzo[d]oxazole derivative

The invention discloses a preparation method of a benzo[d]oxazole derivative, namely 2-chlorobenzo[d]oxazole-5-formamide. With 2-nitro-4-cyanophenol being an initial raw material, the target product is obtained through reducing, ring closure, chlorinating

Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3- triazoles

Novel dicationic triazoles 1-60 were synthesized by the Pinner method from the corresponding dinitriles, prepared via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The type and the placement of cationic moieties as well as the nature of arom

COMPOUNDS WHICH HAVE ACTIVITY AT M1 RECEPTOR AND THEIR USES IN MEDICINE

Compounds of formula (I) or a salt thereof are provided: wherein R4, R6, R7, R8, Q, A, Y, n are as defined in the description. Uses of the compounds as medicaments and in the manufacture of medicaments for treat

2-Arylbenzoxazoles as CETP inhibitors: Substitution and modification of the α-alkoxyamide moiety

The development of a series of 2-arylbenzoxazole α-alkoxyamide and β-alkoxyamine inhibitors of cholesteryl ester transfer protein (CETP) is described. Highly fluorinated α-alkoxyamides proved to be potent inhibitors of CETP in vitro, and the highly fluorinated 2-arylbenzoxazole β-alkoxyamine 4 showed a desirable combination of in vitro potency (IC50 = 151 nM) and oral bioavailability in the mouse.