50597-19-8

Basic information

• Product Name: 4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID
• Synonyms: 4-(3,4-DICHLOROPHENYL)-4-OXOBUTANOIC ACID;4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID;AKOS AKM00953;OTAVA-BB 1043527
• CAS NO: 50597-19-8
• Molecular Formula: C₁₀H₈Cl₂O₃
• Molecular Weight: 247.07
• Mol File: 50597-19-8.mol

Chemical Properties

• Melting Point: 166-167 °C(Solv: ethanol (64-17-5))
• Boiling Point: 447.1 °C at 760 mmHg
• Flash Point: 224.2 °C
• Appearance: /
• Density: 1.432 g/cm³
• Vapor Pressure: 8.9E-09mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.30±0.17(Predicted)
• CAS DataBase Reference: 4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID(50597-19-8)
• EPA Substance Registry System: 4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID(50597-19-8)

Safety Data

• Hazardous Substances Data: 50597-19-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and improve the efficacy of existing ones. Its unique chemical structure allows it to be a versatile building block in the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID is utilized as a precursor in the production of agrochemicals, specifically pesticides and herbicides. Its role in these applications is to enhance crop protection and increase agricultural productivity by controlling pests and weeds effectively.
Used in Organic Synthesis:
4-(3,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID is employed as a key component in organic synthesis for its capacity to form a variety of chemical compounds. Its reactivity and structural properties make it an essential part of the synthesis process, contributing to the creation of new materials and compounds across different fields.

InChI:InChI=1/C10H8Cl2O3/c11-7-2-1-6(5-8(7)12)9(13)3-4-10(14)15/h1-2,5H,3-4H2,(H,14,15)

Upstream product

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Downstream Products

• 147189-99-9 4-(3,4-Dichlorophenyl)-4-oxobutanoic acid 1,1-dimethylethyl ester 
• 36725-34-5 6-(3,4-dichlorophenyl)-4,5-dihydro-3(2H)-pyridazinone 
• 95652-74-7 methyl 4-(3',4'-dichlorophenyl)-4-oxo-butanoate 
• 191673-42-4 methyl 4-(3,4-dichlorophenyl)-4-pentenoate 
• 191673-43-5 tert-butyl-[4-(3,4-dichloro-phenyl)-pent-4-enyloxy]-dimethyl-silane 
• 191673-46-8 (2R)-1-amino-5-(t-butyldimethylsilyloxy)-2-(3,4-dichlorophenyl)-2-pentanol 
• 191673-44-6 (2R)-5-(t-butyldimethylsilyloxy)-2-(3,4-dichlorophenyl)pentane-1,2-diol 
• 191673-45-7 (2R)-1-azido-5-(t-butyldimethylsilyloxy)-2-(3,4-dichlorophenyl)-2-pentanol 
• 95609-48-6 rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one 
• 79560-19-3 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 25157-66-8 4-(3,4-dichlorophenyl)butanoic acid 
• 147189-93-3 (R)-(+)-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one 
• 118528-87-3 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid 

Relevant articles and documents

Utility of novel 2-furanones in synthesis of other heterocyclic compounds having anti-inflammatory activity with dual COX2/LOX inhibition

Inflammation is associated with the development of several diseases comprising cancer and cardiovascular disease. Agents that suppress cyclooxygenase (COX) and lipoxygenase (LOX) enzymes, besides chemokines have been suggested to minimise inflammation. Here, a variety of novel heterocyclic and non-heterocyclic compounds were prepared from novel three furanone derivatives. The structures of all synthesised compounds were confirmed by elemental and spectral analysis including mass, IR, and 1H-NMR spectroscopy. Anti-inflammatory activities of these synthesised compounds were examined in?vitro against COX enzymes, 15-LOX, and tumour necrosis factor-α (TNF-α), using inhibition screening assays. The majority of these derivatives showed significant to high activities, with three pyridazinone derivatives (5b, 8b, and 8c) being the most promising anti-inflammatory agents with dual COX-2/15-LOX inhibition activities along with high TNF-α inhibition activity.

A biphenyl inhibitor of eIF4E targeting an internal binding site enables the design of cell-permeable PROTAC-degraders

The eukaryotic translation initiation factor 4E (eIF4E) is the master regulator of cap-dependent protein synthesis. Overexpression of eIF4E is implicated in diseases such as cancer, where dysregulation of oncogenic protein translation is frequently observed. eIF4E has been an attractive target for cancer treatment. Here we report a high-resolution X-ray crystal structure of eIF4E in complex with a novel inhibitor (i4EG-BiP) that targets an internal binding site, in contrast to the previously described inhibitor, 4EGI-1, which binds to the surface. We demonstrate that i4EG-BiP is able to displace the scaffold protein eIF4G and inhibit the proliferation of cancer cells. We provide insights into how i4EG-BiP is able to inhibit cap-dependent translation by increasing the eIF4E-4E-BP1 interaction while diminishing the interaction of eIF4E with eIF4G. Leveraging structural details, we designed proteolysis targeted chimeras (PROTACs) derived from 4EGI-1 and i4EG-BiP and characterized these on biochemical and cellular levels. We were able to design PROTACs capable of binding eIF4E and successfully engaging Cereblon, which targets proteins for proteolysis. However, these initial PROTACs did not successfully stimulate degradation of eIF4E, possibly due to competitive effects from 4E-BP1 binding. Our results highlight challenges of targeted proteasomal degradation of eIF4E that must be addressed by future efforts.

Asymmetric hydrogenation reaction γ - or δ - ketonato compound (by machine translation)

The invention relates to the field, of organic chemistry, specifically γ - or δ - keto acid compound asymmetric hydrogenation reaction, reaction formula as follows : Wherein R is H,C. 1 - C6 An alkyl or halogen, is R 1 - 5 in number of substituents . wherein n is 1 or 2;Cat. is a chiral spiro pyrimidyl phosphine ligand iridium complex . and γ - or δ - keto acid compound is subjected to an internal esterification reaction to further prepare a lactone compound. (by machine translation)

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.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.

NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF

Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents

A series of new hybrid benzimidazole containing pyridazinones derivatives were designed and synthesized in accordance with the pharmacophoric requirements essential for the anticonvulsant activity. The synthesized compounds were evaluated for anticonvulsant activity on mice by the gold standard maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models. Among the compounds tested, SS-4F showed significant anticonvulsant activity in both the screens with ED50 values of 25.10 and 85.33 mg/kg in the MES and scPTZ screens, respectively. Compound SS-4F emerged as safer and effective anticonvulsant due to its several-fold higher protective indices. Further, the gamma-aminobutyric acid (GABA) estimation result showed a marked increase in the GABA level (1.7-fold) as compared to the control, which was further confirmed by good binding properties with the GABAA receptor.

NOVEL PYRIDAZONES AND TRIAZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula wherein R1, R2, R3, X and a are as described in the description and in the claims, as well as or pharmaceutically acceptable salts thereof. The invention also contains compositions including the compounds and methods of using the compounds.

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