3984-34-7

Usage

Uses

Used in Chemical Synthesis:
3-(4-Chlorobenzoyl)propionic acid is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity in Pd-mediated Suzuki-Miyaura cross-coupling reactions with arylboronic acids, involving nucleophilic N-heterocyclic carbenes as ancillary ligands, makes it a valuable component in the development of new molecules with specific applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(4-Chlorobenzoyl)propionic acid is used as a building block for the development of new drugs. Its unique chemical structure allows it to be a key component in the synthesis of various therapeutic agents, potentially contributing to the treatment of various diseases and conditions.
Used in Research and Development:
3-(4-Chlorobenzoyl)propionic acid is also utilized in research and development settings, where it can be employed to study the properties and behavior of aryl chlorides in different chemical reactions. This knowledge can be applied to improve existing synthetic methods or develop new ones, ultimately leading to the creation of novel compounds with specific applications in various industries.

InChI:InChI=1/C10H9ClO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-4H,5-6H2,(H,13,14)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 108-90-7 chlorobenzene 
• 40394-87-4 4-(4-chloro-phenyl)-4-oxo-butyronitrile 
• 7148-01-8 methyl 4-(4-chlorophenyl)-4-oxobutanoate 
• 51833-36-4 4-chlorophenylmagnesium chloride 
• 29582-39-6 (E)-4-oxo-4-(4-chloro-phenyl)-but-2-enoic acid 
• 292638-85-8 acrylic acid methyl ester 
• 33599-26-7 α-(4-Chlorophenyl)-4-morpholineacetonitrile 
• 99-91-2 para-chloroacetophenone 
• 29582-39-6 3-(4-chlorobenzoyl)acrylic acid 
• 873-77-8 (4-chlorphenyl)magnesium bromide 

Downstream Products

• 340283-98-9 butyl 4-(4-chlorophenyl)-4-oxobutanoate 
• 114215-65-5 5-(4-chlorophenyl)-3-(2-thienylmethylene)-2(3H)-furanone 
• 100046-80-8 (E)-5-(4-chlorophenyl)-3-(2-thienylmethylene)-2(3H)-furanone 
• 100046-84-2 (Z)-5-(4-chlorophenyl)-3-(2-thienylmethylene)-2(3H)-furanone 
• 129973-61-1 (E)-5-(4-chlorophenyl)-3-(5-methyl-2-furylmethylene)-2(3H)-furanone 
• 117808-91-0 3-(4-chlorobenzoyl)-3-butenoic acid 
• 84023-91-6 (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-5-(4-chlorophenyl)-furan-2(3H)-one 
• 127941-47-3 ethyl 2-[3-(4-chlorophenyl)-6-oxo-4,5-dihydropyridazin-1-yl]acetate 
• 135275-72-8 4-(4-Chloro-phenyl)-4-[(4-methyl-5-nitro-thiazol-2-yl)-hydrazono]-butyric acid 
• 4619-18-5 4-(4-chlorophenyl)butanoic acid 
• 19967-22-7 4-(p-chlorophenyl)-1-butanol 
• 124-38-9 carbon dioxide 
• 74-11-3 para-chlorobenzoic acid 
• 115073-03-5 7-chloro-3a-(4-chlorophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one 

Relevant academic research and scientific papers

Nickel-Catalyzed Asymmetric Hydrogenation of γ-Keto Acids, Esters, and Amides to Chiral γ-Lactones and γ-Hydroxy Acid Derivatives

A highly efficient asymmetric hydrogenation of a series of γ-keto acid derivatives, including γ-keto acids, esters, and amides, using a Ni-(R,R)-QuinoxP? complex as the catalyst has been developed to afford chiral γ-hydroxy acid derivatives with excellent enantioselectivities, up to 99.9% ee. This method provides not only an economical one-pot approach for the synthesis of chiral γ-lactones but also access to (S)-norfluoxetine, an inhibitor of neural serotonin reuptake and an essential intermediate for pharmaceutical synthesis.

In silico designing, in vitro and in vivo evaluation of potential PPAR-γ agonists derived from aryl propionic acid scaffold

Attributed to several side effects, especially on hepatic tissues and body weight, there is always an urge of innovation and upgrading in already existing medication being used in maintaining diabetic condition. Therefore, in the present work, forty-eight molecules derived from arylpropionic acid scaffold were synthesized and their evaluation against diabetes was carried out. The synthesis of these molecules attributed to excellent dock score displayed by all the structures performed against PPAR-γ receptor site. Subsequently, all the derivatives were primarily deduced for their antidiabetic potential by OGTT. The compounds that showed significant antidiabetic activity in OGT Test and also exhibited high dock scores were assessed further by in vitro PPAR transactivation assay to assure analogy between in vivo and in vitro studies. The antidiabetic activity of these active compounds was then evaluated on STZ induced diabetic model in vivo. The most active compounds were scrutinized for its effect on PPAR-γ gene expression and hepatotoxic effect. Finally, it was recapitulated that these derivatives can provide a new prospect towards the development of antidiabetic agents with fewer side effects.

Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation

Multiple sclerosis (MS) is an autoimmune demyelinating disease of the central nervous system (CNS) that causes severe motor, sensory, and cognitive impairments. Kallikrein-related peptidase (KLK)6 is the most abundant serine protease secreted in the CNS, mainly by oligodendrocytes, the myelin-producing cells of the CNS, and KLK6 is assumed to be a robust biomarker of MS, since it is highly increased in the cerebrospinal fluid (CSF) of MS patients. Here, we report the design and biological evaluation of KLK6's low-molecular-weight inhibitors, para-aminobenzyl derivatives. Interestingly, selected hit compounds were selective of the KLK6 proteolytic network encompassing KLK1 and plasmin that also participate in the development of MS physiopathology. Moreover, hits were found noncytotoxic on primary cultures of murine neurons and oligodendrocyte precursor cells (OPCs). Among them, two compounds (32 and 42) were shown to promote the differentiation of OPCs into mature oligodendrocytes in vitro constituting thus emerging leads for the development of regenerative therapies.

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.

BEXAROTENE DERIVATIVES AND THEIR USE IN TREATING CANCER

This disclosure relates to compositions and methods for treating cancer. Specifically, this disclosure relates to bexarotene derivatives, methods for treating cancer, autoimmune disorders, and/or skin dermatitis, and/or methods for increasing peripheral blood counts and/or improving immune system function.

One-Pot Synthesis of 2,5-Disubstituted Furans through In Situ Formation of Allenes and Enolization Cascade

A one-pot synthesis of 2,5-disubstituted furans from γ-ketoacids is reported. In situ formation of allenoates by action of chloroformate on carboxylic acid following by enolization of ketone affords furan derivatives by cyclization. The reaction was extended to a wide scope of ketoacids and phosphonium salts. This methodology was applied on levulinic acid and derivatives, one of the biosourced platform chemicals.

Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation

A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.

Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines

By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.

Design, synthesis, and bioactive screen in vitro of cyclohexyl (E)-4-(Hydroxyimino)-4-phenylbutanoates and their ethers for anti-Hepatitis B Virus agents

A series of oxime Cyclohexyl (E)-4-(hydroxyimino)-4-phenylbutanoates and their ethers were designed, synthesized, and evaluated for anti-hepatitis B virus (HBV) activities with HepG 2.2.15 cell line in vitro. Most of these compounds possessed anti-HBV activities, and among them, compound 4B-2 showed significant inhibiting effects on the secretion of HBsAg (IC50 = 63.85 ± 6.26 μM, SI = 13.41) and HBeAg (IC50 = 49.39 ± 4.17 μM, SI = 17.34) comparing to lamivudine (3TC) in HBsAg (IC50 = 234.2 ± 17.17 μM, SI = 2.2) and HBeAg (IC50 = 249.9 ± 21.51 μM, SI = 2.07). Docking study of these compounds binding to a protein residue (PDB ID: 3OX8) from HLA-A2 that with the immunodominant HBcAg18-27 epitope (HLA-A2.1- restricted CTL epitope) active site was carried out by using molecular operation environment (MOE) software. Docking results showed that behaviors of these compounds binding to the active site in HLA-A protein residue partly coincided with their behaviors in vitro anti-HBV active screening.