13575-74-1

Usage

Uses

Used in Pharmaceutical Applications:
4-(3,4-DIMETHOXYPHENYL)BUTYRIC ACID is used as a pharmaceutical agent for its effects on apoptosis, proliferation, and HDAC activity in HT-29 colorectal cancer cells. This suggests its potential use in the development of treatments for colorectal cancer and possibly other types of cancer.
Used in Chemical Synthesis Studies:
4-(3,4-DIMETHOXYPHENYL)BUTYRIC ACID is used as a key compound in chemical synthesis studies. Its unique structure and properties make it a valuable building block for the development of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C12H16O4/c1-15-10-7-6-9(8-11(10)16-2)4-3-5-12(13)14/h6-8H,3-5H2,1-2H3,(H,13,14)

Upstream product

• 124-38-9 carbon dioxide 
• 3945-85-5 1-bromo-3-(3,4-dimethoxyphenyl)propane 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 91-16-7 1,2-dimethoxybenzene 
• 3929-47-3 3-(3,4-dimethoxyphenyl)-1-propanol 
• 2107-70-2 3,4-methoxycinnamic acid 
• 137744-82-2 C₁₂H₁₄O₄ 
• 231935-01-6 ethyl 4-(3,4-dimethoxyphenyl)butanoate 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 64-18-6 formic acid 
• 348143-75-9 4-(3,4-dimethoxyphenyl)butanoic acid chloride 
• 121213-49-8 9-((CH₂)3(C₆H₄)(OMe)2)-9-borabicyclo{3.3.1}nonane 
• 2316-26-9 3,4-dimethoxycinnamic acid 

Downstream Products

• 231935-01-6 ethyl 4-(3,4-dimethoxyphenyl)butanoate 
• 56880-86-5 4-(3,4-dimethoxyphenyl)butan-1-ol 
• 56242-82-1 4-(2-chloro-4,5-dimethoxyphenyl)butyric acid 
• 54549-75-6 6,7-dihydroxy-3,4-dihydro-1(2H)-naphthalenone 
• 802985-69-9 4-(2-bromo-4,5-dimethoxy-phenyl)-butyric acid 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 348143-75-9 4-(3,4-dimethoxyphenyl)butanoic acid chloride 
• 14335-78-5 5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one 

Relevant academic research and scientific papers

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 and evaluation of 7-substituted-5,6-dihydrobenzo[c]acridine derivatives as new c-KIT promoter G-quadruplex binding ligands

It has been shown that treatment of cancer cells with c-KIT G-quadruplex binding ligands can reduce their c-KIT expression levels thus inhibiting cell proliferation and inducing cell apoptosis. Herein, a series of new 7-substituted-5,6-dihydrobenzo[c]acri

Dopaminergic Agonists: Comparative Actions of Amine and Sulfonium Analogues of Dopamine

We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine.A series of methyl- tetralinyl-, and naphthalenylsul

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.

Synthesis of rigidified eIF4E/eIF4G inhibitor-1 (4EGI-1) mimetic and their in vitro characterization as inhibitors of protein-protein interaction

The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro ch

Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach

Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.

Expeditious approach to pyrrolophenanthridones, phenanthridines, and benzo[ c ]phenanthridines via organocatalytic direct biaryl-coupling promoted by potassium tert -butoxide

A methodology involving a "transition metal-free" intramolecular biaryl-coupling of o-halo-N-arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KOtBu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our approach further, we found that N-acyl 2-bromo-N-arylbenzylamines undergo a one-pot N-deprotection/biaryl coupling followed by oxidation, thus offering an expeditious route to the phenanthridine and benzo[c]phenanthridine skeletons. The strategy has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), 5,6-dihydrobicolorine (2d), trispheridine (2b), and benzo[c]phenanthridines alkaloids dihydronitidine (3b), dihydrochelerythidine (3d), dihydroavicine (3f), nornitidine (3h), and norchelerythrine (3j).

12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy tra