85-57-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Hydroxybenzoyl)benzoic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its presence in the molecular structure of certain compounds can enhance their therapeutic properties, making it an essential component in drug discovery and formulation.
Used in Cosmetic Industry:
In the cosmetic industry, 2-(4-Hydroxybenzoyl)benzoic acid is utilized as an antioxidant ingredient in skincare products. Its potent antioxidant properties help protect the skin from oxidative stress and environmental damage, contributing to the development of effective skincare formulations that promote skin health and longevity.
Used in Organic Synthesis:
2-(4-Hydroxybenzoyl)benzoic acid is used as a building block in organic synthesis for its versatility in forming various organic compounds. Its unique molecular structure allows for the creation of a wide array of chemical entities, making it an indispensable tool in the synthesis of complex organic molecules for various applications.

InChI:InChI=1/C14H10O4/c15-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)14(17)18/h1-8,15H,(H,17,18)

Upstream product

• 85-44-9 phthalic anhydride 
• 108-95-2 phenol 
• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 7649-92-5 2-(4-fluorobenzoyl)benzoic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 77-09-8 phenolphthalein 
• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 
• 854-76-2 [3-(3'-methyl-4'-hydroxyphenyl)-3-(4''-hydroxyphenyl)phthalide] 
• 193630-25-0 3-(4''-hydroxyphenyl)-3-(3'-ethyl-4'-hydroxyphenyl)phthalide 
• 193630-26-1 3-(4''-hydroxyphenyl)-3-(4'-hydroxy-3'-isopropylphenyl)phthalide 
• 7664-93-9 sulfuric acid 
• 856807-89-1 3-acetoxy-3-(4-acetoxy-phenyl)-phthalide 
• 7446-70-0 aluminium trichloride 
• 79-34-5 1,1,2,2-tetrachloroethane 

Downstream Products

• 21147-23-9 2-(4-hydroxybenzoyl)benzoic acid methyl ester 
• 65133-93-9 2-(4-hydroxy-benzoyl)-benzoic acid ethyl ester 
• 1447-90-1 3-(4-hydroxy-5-isopropyl-2-methyl-phenyl)-3-(4-hydroxy-phenyl)-3H-isobenzofuran-1-one 
• 7468-76-0 3-(4'-hydroxyphenyl)phthalide 
• 14660-14-1 2-(4'-hydroxybenzyl)benzoic acid 
• 861782-57-2 2-(3,5-dichloro-4-hydroxy-benzoyl)-benzoic acid 
• 871881-27-5 2-(3,5-dibromo-4-hydroxy-benzoyl)-benzoic acid 
• 43046-97-5 NCS₁₅₃₆₈ 
• 1137-42-4 4-Hydroxybenzophenone 
• 856807-89-1 3-acetoxy-3-(4-acetoxy-phenyl)-phthalide 
• 1241-41-4 3-(3,4-dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-phthalide 

Relevant academic research and scientific papers

A facile greener synthesis, antimicrobial evaluation and molecular modelling of new 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one derivatives

Abstract: The synthesis of 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-ones was performed by cyclization of 2-hydrazinyl-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine with 2-aroylbenzoic acids in ethanol containing a catalytic amount of concentrated sulfuric acid under solid state conditions. All these synthesized compounds (8a–h) were screened for their in vitro antibacterial activity against gram-positive bacteria such as (Staphylococcus aureus) and gram-negative bacteria (Escherichia coli) and also evaluated for their antifungal activity against Aspergillus Niger and Helmenthosphorium oryzae fungal strains. Some of the products demonstrate good antibacterial activity and moderate antifungal activity. In predominantly, 8b, 8d, 8g, and 8h compounds showed good to excellent antibacterial and antifungal activities. The antimicrobial activity of the compound 8 was further investigated with the help of in LibDock score docking study to predict the active sites. Graphical abstract: [Figure not available: see fulltext.].

Preparation method of 2-(4-hydroxybenzoyl)benzoic acid

The invention belongs to the technical fields of fine chemical engineering and preparation of drug intermediates, and particularly relates to a preparation method of 2-(4-hydroxybenzoyl)benzoic acid. The preparation method comprises the following steps: heating and refluxing anisole and phthalic anhydride under the action of a Lewis acid catalyst to conduct a friedel-crafts acylation reaction to obtain an intermediate 2-(4-methoxybenzoyl) benzoic acid, then heating and refluxing under the action of a hydrobromic acid solution to sufficiently react to prepare the 2-(4-hydroxybenzoyl)benzoic acid of the target product. Compared with the prior art, the prepared 2-(4-hydroxybenzoyl)benzoic acid is good in quality and higher in yield, and the preparation method is simple in preparation process, mild in conditions, low in energy consumption, low in cost and suitable for mass production.

Rational Design of a Near-Infrared Fluorescent Probe Based on a Pyridazinone Scaffold

A class of pyridazinone derivatives as near-infrared optical probes in fluorescence microscopy images was designed. The design strategy consisted of the stepwise extension and modification of pyridazinone by expansion of the electron-donating moiety to a larger π-conjugated system and anchoring a subcellular directing group such as triphenylphosphine or morpholine. All the desired products were successfully applied in cell imaging with high subcellular colocalization. Furthermore, these fluorescent probes showed excellent performance in mouse-brain imaging.

Rational Design of Fluorescent Phthalazinone Derivatives for One- and Two-Photon Imaging

Phthalazinone derivatives were designed as optical probes for one- and two-photon fluorescence microscopy imaging. The design strategy involves stepwise extension and modification of pyridazinone by 1) expansion of pyridazinone to phthalazinone, a larger conjugated system, as the electron acceptor, 2) coupling of electron-donating aromatic groups such as N,N-diethylaminophenyl, thienyl, naphthyl, and quinolyl to the phthalazinone, and 3) anchoring of an alkyl chain to the phthalazinone with various terminal substituents such as triphenylphosphonio, morpholino, triethylammonio, N-methylimidazolio, pyrrolidino, and piperidino. Theoretical calculations were utilized to verify the initial design. The desired fluorescent probes were synthesized by two different routes in considerable yields. Twenty-two phthalazinone derivatives were synthesized and their photophysical properties were measured. Selected compounds were applied in cell imaging, and valuable information was obtained. Furthermore, the designed compounds showed excellent performance in two-photon microscopic imaging of mouse brain slices.

The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1

Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R1) and benzoyl (R2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and log D) and excellent rat pharmacokinetics (e.g., rat oral bioavailability of 89% for compound 17).

Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

An efficient and economical synthesis of some new fluorine substituted phthalides was accomplished from two γ-keto acids, 2-(4-fluorobenzoyl) benzoic acid and 2-(3,5-dinitro-4-flurobenzoyl)benzoic acid. Each acid was reacted with various phenolic compounds in presence of catalytic quantity of concentrated sulphuric acid to get the phthalides. The structures of the synthesized compounds were established on the basis of their elemental analysis, spectral data and chemical reactions. Some of the synthesized phthalides exhibited antibacterial and antifungal activity on antimicrobial screening against human pathogenic bacteria and fungi.

Small-molecule inhibitors of the MDM2-p53 protein-protein interaction based on an isoindolinone scaffold

From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3- dihydroisoindol-1-one (76; IC50 = 15.9 ± 0.8 μM) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2, 3-dihydroisoindol-1-one (79; IC50 = 5.3 ± 0.9 μM), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.

ISOINDOLIN-1-ONE DERIVATIVES

A compound of formula (1) or a prodrug and/or pharmaceutically acceptable salt thereof, wherein X is selected from O, N or S; R1 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; R2 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; R3 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alloy substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; and R4-R7, is used to represent groups R4, R5, R6 and R7 which are independently selected from H, OH, alkyl, alkoxy, alkylamine, hydroxyalkyl, halo, CF3, NH2, NO2, COOH, C=0.

Non-Peptidic Small-Molecule Inhibitors of the Single-Chain Hepatitis C Virus NS3 Protease/NS4A Cofactor Complex Discovered by Structure-Based NMR Screening

NMR-based screening of a customized fragment library identified 16 small-molecule hits that bind weakly (KD ≈ 100 μM to 10 mM) to substrate binding sites of the NS4A-bound NS3 protease of the hepatitis C virus (HCV). Analogues for five classes of NMR hits were evaluated by a combination of NMR and biochemical data yielding SAR and, in most cases, optimized hits with improved potencies (KD ≈ KI ≈ 40 μM to mM). NMR chemical shift perturbation data were used to establish the binding location and orientation of the active site directed scaffolds in these five analogue series. Two of these scaffolds, which bind the enzyme at the proximal S1-S3 and S2′ substrate binding sites, were linked together producing competitive inhibitors of the HCV NS3 protease with potencies in the micromolar range. This example illustrates that the low molecular weight scaffolds discovered from structure-based NMR screening can be optimized with focused structure-guided chemistry to produce potent nonpeptidic small-molecule inhibitors of the HCV NS3 protease.

3,3-Diarylphthalides. Part I. Friedlaender reaction of 3′-alkylphenolphthaleins

Friedlaender reaction was investigated, starting from 3′-alkyl-derivatives of phenolphthalein 1-3 (alkyl = Me, Et and i-Pr) and hydroxylamine in strongly alkaline medium. The process was found to give, after acidic hydrolysis of primarily formed anil-type semi-products, a mixture of two 2-aroylbenzoic acids (2-ABAs) in each case. Identification and quantification of 2-ABAs were carried out within RP-HPLC on ODS column. Based on quantitative results, migratory aptitude (MA) parameter values of ionized 4-hydroxy-3-alkylphenyl nuclei were calculated, taking an unsubstituted ionized 4-hydroxyphenyl ring as a standard.