1693-37-4

Usage

Uses

Used in Pharmaceutical Industry:
ACETAMINOPHEN IMPURITY B is used as a reference material for quality control and analytical testing in the pharmaceutical industry. It helps ensure the purity and safety of Acetaminophen products, which are used as pain relievers to treat conditions such as headache, muscle aches, and arthritis.

InChI:InChI=1/C9H11NO2/c1-2-9(12)10-7-3-5-8(11)6-4-7/h3-6,11H,2H2,1H3,(H,10,12)

Upstream product

• 123-30-8 4-amino-phenol 
• 123-62-6 propionic acid anhydride 
• 802294-64-0 propionic acid 
• 457-74-9 N-(4-fluoro-phenyl)-propionamide 
• 100-02-7 4-nitro-phenol 
• 111359-74-1 4-[(tert-butyldimethylsilyl)oxy]aniline 
• 63579-08-8 N-(p-propionyloxyphenyl)propionamide 

Downstream Products

• 63579-08-8 N-(p-propionyloxyphenyl)propionamide 
• 28763-47-5 N-<4-(2,3-epoxypropoxy)phenyl>propionamide 
• 78953-38-5 N-[4-((2R,3S)-3-Ethylamino-2-hydroxy-butoxy)-phenyl]-propionamide 
• 78953-39-6 N-[4-((2R,3S)-2-Hydroxy-3-isopropylamino-butoxy)-phenyl]-propionamide 
• 78953-40-9 N-[4-((2S,3R)-3-tert-Butylamino-2-hydroxy-butoxy)-phenyl]-propionamide 
• 35268-56-5 4'-{2-[4-(p-methoxyphenyl)-3,6-dihydro-1(2H)-pyridyl]ethoxy}acetanilide 
• 1383479-31-9 C₂₈H₃₀N₂O₄ 
• 19314-99-9 1-Isopropylamino-3-(p-propionylaminophenoxy)-propanol-⁽²⁾ 
• 692249-91-5 acetic acid-(4-hydroxy-N-methyl-3-nitro-anilide) 

Relevant academic research and scientific papers

VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics

We report the optimisation of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced apomorphine-induced climbing, MK-801-induced hyperactivity and DOI-induced head twitching without observable catalepsy, even at the highest dose tested. In addition, it exhibited suppression in a CAR test. Furthermore, in a novel object recognition task, it displayed procognition properties. Therefore, compound 11 is a promising candidate multi-target antipsychotic.

Analysis of chain length, substitution patterns, and unsaturation of AM-404 derivatives as 20S proteasome stimulators

Proteasome-mediated degradation of proteins is a vital cellular process and is performed by the ubiquitin-dependent proteasome system (UPS) and the ubiquitin-independent proteasome system (UIPS). While both systems are necessary to maintain healthy cell function, many disease states are characterized by reduced activity of the UPS, and the UIPS cannot by itself maintain proper protein levels. It has been suggested that the 20S core particle (20S CP), the isoform of the proteasome in the UIPS that can degrade proteins without a ubiquitin tag, can be stimulated with a small molecule to assist the 20S CP to accept and hydrolyze substrates more rapidly. Several small molecule stimulators of the 20S CP have since been discovered, including AM-404, an arachidonic acid derivative. AM-404 has previously been shown to inhibit fatty acid amide hydrolase activity. We wished to evaluate what structural components of AM-404 are required to stimulate the 20S CP with the long-term goal of using this information to design a stimulator with better drug-like qualities. We synthesized numerous derivatives of AM-404, varying the chain length, substitutions, and degree of unsaturation. Through this endeavor, we obtained several molecules capable of stimulating the 20S CP to various degrees. We discovered that though chain length is important, the presence of a cis-alkene in a specific location in the aliphatic chain has the greatest impact on the ability to stimulate the 20S CP. Two of the derivatives maintain modest stimulatory activity, and have improved toxicity over AM-404.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

Reductive acylation of nitroarenes to anilides by sodium sulfite in carboxylic acids

A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite-carboxylic acid system for the first time has been reported. The sodium sulfite reagent provides the colorless reductant in combination with stoichiometric amounts of carboxylic acid and enables the formation of anilides from nitroarenes without any additives in good to excellent yields with high purities and simple work-up. Furthermore, this protocol provides a novel and complementary access to some industrially important chemicals in kilogram scale under mild conditions.

Synthesis and SAR of selective small molecule neuropeptide y Y2 receptor antagonists

Highly potent and selective small molecule neuropeptide Y Y2 receptor antagonists are reported. The systematic SAR exploration of a hit molecule N-(4-ethoxyphenyl)-4-[hydroxy(diphenyl)methyl]piperidine-1-carbothioamide, identified from HTS, led to the discovery of highly potent NPY Y2 antagonists 16 (CYM 9484) and 54 (CYM 9552) with IC50 values of 19 nM and 12 nM respectively.

New, efficient, selective, and one-pot method for acylation of amines

Hydrazine hydrate with acetic and propionic acids was an efficient reagent for acylation of primary and secondary amines at reflux temperatures. The reported one-pot method is high-yielding, simple, mild, and inexpensive. Copyright Taylor & Francis Group, LLC.

Chemoselective acylation of amines in aqueous media

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Boronic ester as a linker system for solid phase synthesis

A method for attaching boronic acids to a macroporous polymer-supported 1,3-diol was developed. Chemical modifications of some polymer-bound arylboronic acids were realised using various reaction conditions. Trans-esterification gave new boronates in high purity while oxidative cleavage directly led to phenols.

Evaluation of dynamic polar molecular surface area as predictor of drug absorption: Comparison with other computational and experimental predictors

The relationship between various molecular descriptors and transport of drugs across the intestinal epithelium was evaluated. The monolayer permeability (P(c)) of human intestinal Caco-2 cells to a series of nine β- receptor-blocking agents was investigated in vitro. The dynamic polar molecular surface area (PSA(d)) of the compounds was calculated from all low- energy conformations identified in molecular mechanics calculations in vacuum and in simulated chloroform and water environments. For most of the investigated drugs, the effects of the different environments on PSA(d) were small. The exception was H 216/44, which is a large flexible compound containing several functional groups capable of hydrogen bonding (PSA(d,chloroform) = 70.8 A?2 and PSA(d,water) = 116.6 A?2). The relationship between P(c) and PSA(d) was stronger than those between Pc and the calculated octanol/water distribution coefficients (log D(calc)) or the experimentally determined immobilized liposome chromatography (ILC) retention. P(c) values for two new practolol analogues and H 216/44 were predicted from the structure-permeability relationships of a subset of the nine compounds and compared with experimental values. The P(c) values of the two practolol analogues were predicted well from both PSA(d) calculations and ILC retention studies. The P(c) value of H 216/44 was reasonably well- predicted only from the PSA(d) of conformations preferred in vacuum and in water. The other descriptors overestimated the Pc of H 216/44 100-500-fold.