18495-15-3

Basic information

• Product Name: 3-HYDROXY-4-NITROBENZONITRILE
• Synonyms: 4-NITRO-3-HYDROXY-BENZONITRILE;3-HYDROXY-4-NITROBENZONITRILE;2-Nitro-5-cyanophenol
• CAS NO: 18495-15-3
• Molecular Formula: C₇H₄N₂O₃
• Molecular Weight: 164.12
• Mol File: 18495-15-3.mol

Chemical Properties

• Boiling Point: 313.6 °C at 760 mmHg
• Flash Point: 143.5 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 0.000266mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-HYDROXY-4-NITROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-NITROBENZONITRILE(18495-15-3)
• EPA Substance Registry System: 3-HYDROXY-4-NITROBENZONITRILE(18495-15-3)

Safety Data

• Hazardous Substances Data: 18495-15-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-HYDROXY-4-NITROBENZONITRILE is used as a key intermediate in the synthesis of arylbenzoxazoles, which are known for their cholesterol ester transfer protein (CETP) inhibitory properties. CETP inhibitors play a crucial role in the regulation of high-density lipoprotein (HDL) and low-density lipoprotein (LDL) cholesterol levels, making them potential candidates for the treatment of cardiovascular diseases.
In the synthesis of arylbenzoxazoles, 3-HYDROXY-4-NITROBENZONITRILE serves as a starting material, which can be further modified and functionalized to develop CETP inhibitors with improved pharmacological properties. These inhibitors can be used in the development of drugs for the treatment of conditions such as atherosclerosis, coronary artery disease, and other related cardiovascular disorders.
Additionally, 3-HYDROXY-4-NITROBENZONITRILE may also find applications in other industries, such as the chemical and materials science fields, where its unique structural features can be exploited for the development of novel compounds with specific properties and applications.

InChI:InChI=1/C7H4N2O3/c8-4-5-1-2-6(9(11)12)7(10)3-5/h1-3,10H

Upstream product

• 619-72-7 4-nitrobenzonitrile 
• 873-62-1 m-cyanophenol 

Downstream Products

• 55586-26-0 3-hydroxy-4-aminobenzonitrile 
• 203190-56-1 1-allyloxy-5-cyano-2-nitrobenzene 
• 203201-38-1 5-cyano-1-methoxymethyloxy-2-nitrobenzene 
• 203201-43-8 2-bromo-3-cyano-6-nitrophenol 
• 182499-93-0 2-amino-5-methyl 6-cyanophenol 
• 1380593-13-4 (Z)-2-(3-hydroxy-4-nitrophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one 
• 203190-57-2 4-amino-3-(allyloxy)benzonitrile 
• 203201-39-2 4-Cyano-2-methoxymethyloxyaniline 
• 203201-41-6 2-amino-5-cyano-6-prop-1-ene-3-yl-phenol 
• 203201-42-7 2-Amino-5-cyano-6-propyl-phenol 
• 203190-60-7 N-(2-Allyloxy-4-cyanophenyl)-N'-(2-bromophenyl)-carbodiimide 
• 203190-59-4 N-(2-Allyloxy-4-cyanophenyl)-N'-(2-bromophenyl)-thiourea 
• 203201-29-0 N-(2-bromophenyl)-N'-(4-cyano-2-hydroxy-3-propylphenyl)-N-cyanoguanidine 

Relevant articles and documents

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.

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.

CONDENSED HETEROCYCLIC COMPOUND

A compound represented by the general formula (I) [R1 represents a C1-6 alkyl group, a halogen atom, or the like; A represents a phenylene group, or the like; X represents —CH(R3)—, —O—, —NH—, or the like; Y represents —O—, —NH—, —N═, or —S—; . . . represents a single bond or double bond; n represents 1 to 3; R2 represents a C1-6 alkyl group, a C1-6 alkoxy group, or the like; and R3 represents hydrogen atom, a C1-6 alkyl group, or the like], or a salt thereof which has a blood LDL cholesterol-reducing action, and is useful as an active ingredient of medicaments.

Non-steroidal dissociated glucocorticoid agonists: Indoles as A-ring mimetics and function-regulating pharmacophores

We report a SAR of non-steroidal glucocorticoid mimetics that utilize indoles as A-ring mimetics. Detailed SAR is discussed with a focus on improving PR and MR selectivity, GR agonism, and in vitro dissociation profile. SAR analysis led to compound (R)-33 which showed high PR and MR selectivity, potent agonist activity, and reduced transactivation activity in the MMTV and aromatase assays. The compound is equipotent to prednisolone in the LPS-TNF model of inflammation. In mouse CIA, at 30 mg/kg compound (R)-33 inhibited disease progression with an efficacy similar to the 3 mg/kg dose of prednisolone.

Evaluation of Potent and Selective Small-Molecule Antagonists for the CXCR2 Chemokine Receptor

N,N′-Diarylureas were prepared, and the structure-activity relationship relative to the CXCR2 receptor was examined. This led to the identification of a potent and highly selective CXCR2 antagonist, which in addition was shown to be functionally active bo

IL-8 RECEPTOR ANTAGONISTS

This invention relates to the novel use of phenyl ureas in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones

The compound of the formula: STR1 wherein R1 is straight chain alkyl, branched chain alkyl, cycloalkyl, hydroxyalkyl, fluoroalkyl, or polyfluoroalkyl; and one of R2, R3 and R4 is hydroxyl and the other two are,

Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.

IL-8 RECEPTOR ANTAGONISTS

This invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease scates mediated by the chemokine, Interleukin-8 (IL-8). In particular, this invention relates to the novel compounds of Formula (Ia) and their use in treating chemokine mediated diseases wherein the chemokine binds to an IL-8 a or b receptor. Compounds of Formula (Ia) are represented by the structure: STR1 wherein interalia, X is oxygen or sulfur;Rb is NR 6 R. sub.7, alkcyl, aryl, arylC 1-4 alkyl, aryl C 2-4 alkenyl, heteroaryl, heteroarylC 1-4 alkyl, heteroarylC 2-4 alkenyl, heterocyclic or heterocyclic C 1-4 alkyl, or a heterocyclic C 2-4 alkenyl moiety, camphor, all of which may be optionally substituted; R 1 is independently selected from hydrogen; halogen; nitro; cyano; C 1-10 alkyl; halosubstituted C 1-10 alkyl; C 2-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR. sub.8 R 8)q S(O) t R 4 ; hydroxy; hydroxy substituted C 1-4 alkyl; aryl; aryl C 1-4 alkyl; aryl C 2-10 alkenyl; aryloxy; aryl C 1-4 alkyloxy; heteroaryl; heteroarylalkyl; heteroaryl C 2-10 alkenyl; heteroaryl C 1-4 alkyloxy; heterocyclic; heterocyclic C 1-4 alkyl; heterocyclicC 1-4 alkyloxy; heterocyclic C 2-10 alkenyl; q is 0 or an integer having a value of 1 to 10; n is an integer having a value of 1 to 3;m is an integer having a value of 1 to 3; Y is hydrogen; halogen; nitro; cyano; halosubstituted C 1-10 alkyl; C 1-10 alkyl; C 2-10 alkenyl C. sub.1-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR 8 R. sub.8)qS(O) t R 4, (CR 8 R 8)qOR 4 ; hydorxy; hydroxy substituted C. sub.1-4 alkyl; aryl; aryl C 1-4 alkyl; aryloxy; arylC. sub.1-4 alkyloxy; aryl C 2-10 alkenyl; heteroaryl; heteroarylalkyl; heteroaryl C 1-4 alkyloxy; heteroaryl C 2-10 alkenyl; heterocyclic, heterocyclic C 1-4 alkyl; heterocyclicC 2-10 alkenyl;or a pharmaceutically acceptable salt thereof.

Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol

Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group.A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring .The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series.They correlated well with ? in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with ?p) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with ρm) for pKa2 (the phenol).A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and ?+ (ρ = -1.1).The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated.It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3 - 5) had measurable rates of reduction. 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that compounds 1, 2, 6 - 9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol.The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.