343-67-9

Basic information

• Product Name: ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE;ethyl 4-hydroxy-2-(trifluoromethyl)-5-pyrimidinecarboxylate;Ethyl 4-hydroxy-2-(trifluoromethyl)pyrimidine-5-carboxylate ,97%;ethyl 6-oxo-2-(trifluoroMethyl)-1,6-dihydropyriMidine-5-carboxylate;Ethyl 2-trifluoromethyl-4-oxopyrimidine-5-carboxylate;5-(Ethoxycarbonyl)-4-hydroxy-2-(trifluoromethyl)pyrimidine, 5-(Ethoxycarbonyl)-4-hydroxy-2-(trifluoromethyl)-1,3-diazine
• CAS NO: 343-67-9
• Molecular Formula: C₈H₇F₃N₂O₃
• Molecular Weight: 236.1479896
• Product Categories: pyrimidine;Fluorine series
• Mol File: 343-67-9.mol

Chemical Properties

• Melting Point: 315-316°
• Boiling Point: 220.8 °C at 760 mmHg
• Flash Point: 87.4 °C
• Appearance: /
• Density: 1.50
• Vapor Pressure: 0.0747mmHg at 25°C
• Refractive Index: 1.499
• Storage Temp.: 2-8°C
• PKA: 4.75±0.50(Predicted)
• CAS DataBase Reference: ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(343-67-9)
• EPA Substance Registry System: ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(343-67-9)

Safety Data

• Hazard Codes: Xi
• Statements: 48-20/21/22
• Safety Statements: 3/7/9-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 343-67-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is used as a research reagent for studying the inhibition of NF-κB and AP-1 genes. This is important because these genes play a significant role in regulating cellular responses to various stimuli, including stress, cytokines, and bacterial or viral antigens. By inhibiting these genes, researchers can gain insights into the development of potential therapeutic strategies for various diseases and conditions.
Used in Drug Development:
In the pharmaceutical industry, ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is used as a key intermediate in the synthesis of novel compounds with potential therapeutic applications. Its unique chemical properties make it a valuable building block for the development of new drugs targeting various diseases, including inflammatory disorders, autoimmune conditions, and cancer.
Used in Molecular Biology:
ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is also used in molecular biology as a tool to study gene regulation and signal transduction pathways. By understanding how ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE interacts with NF-κB and AP-1 genes, researchers can develop a better understanding of the underlying mechanisms involved in these processes, which can ultimately lead to the development of targeted therapies for various diseases.

InChI:InChI=1/C8H7F3N2O3/c1-2-16-6(15)4-3-12-7(8(9,10)11)13-5(4)14/h3H,2H2,1H3,(H,12,13,14)

Upstream product

• 37555-99-0 diethyl ethoxymalonate 
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Downstream Products

• 2924-82-5 4-Hydrazino-2-trifluormethyl-pyrimidin-carbonsaeure-(5)-ethylester 
• 720-01-4 ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate 
• 304693-64-9 ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate 

Relevant articles and documents

BENZAMIDE DERIVATIVE COMPOUND, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING INFLAMMATORY DISEASE CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a benzamide derivative compound, a method for preparing the same, and a pharmaceutical composition for treating or preventing an inflammatory disease containing the same as an active ingredient. The benzamide derivative compound according to the present invention inhibits the expression of PDE4 and regulates the expression of an inflammatory disease-related substance such as IL-4 (interleukin-4), IL-5 (interleukin-4), IFN-γ (interferon-γ), IL-17 (interluekin-17), IgE (immunoglobulin E), and TNF-α (tumor necrosis factor-α), and thus may be utilized as a pharmaceutical composition for treating or preventing an inflammatory disease.

Design, synthesis, and biological evaluation of novel catecholopyrimidine based PDE4 inhibitor for the treatment of atopic dermatitis

Selective inhibition of phosphodiesterase (PDE) 4B favorably suppresses the synthesis of inflammatory cytokines and subsequently arrest the development of atopic dermatitis via modulating the intracellular cAMP levels. Considering the side effects of corticosteroids, selective PDE4 inhibition could constitute an effective alternative therapy for the treatment of atopic dermatitis (AD). In this study, a series of novel catechol based compounds bearing pyrimidine as the core have been synthesized and screened for the PDE4 inhibitory properties. The PDE4 selectivity of the active compounds over other PDEs has been investigated. Compound 23 bearing pyrimidine core functionalized with catechol, pyridine and trifluoromethyl groups can effectively inhibit the PDE4B with IC50 value in nanomolar range (IC50 = 15 ± 0.4 nM). Compound 23 exhibited seven fold higher selectivity towards PDE4B over PDE4D. Molecular Docking study confirmed its stronger affinity towards catalytic domain of PDE4B. In-vivo analysis confirmed that compound 23 effectively alleviated the symptoms of atopic dermatitis in DNCB–treated Balb/c mice by suppressing the synthesis of inflammatory mediators such as TNF-α and Ig-E. Taken together, this study suggested that compound 23 could be an effective PDE4 inhibitor for the potential treatment of AD.

Pyrimidinone compounds

Pyrimidinone compounds of formula (I) are inhibitors of the enzyme Lp-PLA2 and of use in therapy, in particular for treating atherosclerosis.

Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].

We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.

Novel inhibitors of AP-1 and NF-κB mediated gene expression: Structure-activity relationship studies of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate

In an effort to identify novel inhibitors of AP-1 and NF-κB mediated transcriptional activation, several analogues of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate (1) were synthesized and tested in two in vitro assays. The 2-(2'-thienyl) substituted compound (11) was identified as the most potent in this series. (C) 2000 Elsevier Science Ltd. All rights reserved.

Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions

Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine-containing compounds and, in one embodiment, are esters of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions

Compounds having utility as antinflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine- or pyrazine-containing compounds and, in one embodiment, are carboxyamides of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.