113264-43-0

Basic information

• Product Name: 3-BroMo-2-oxo-pentanoic acid ethyl ester
• Synonyms: 3-BroMo-2-oxo-pentanoic acid ethyl ester;Ethyl 3-bromo-2-oxopentanoate
• CAS NO: 113264-43-0
• Molecular Formula: C₇H₁₁BrO₃
• Molecular Weight: 223.06444
• Mol File: 113264-43-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 232.307°C at 760 mmHg
• Flash Point: 94.296°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 0.059mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-BroMo-2-oxo-pentanoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BroMo-2-oxo-pentanoic acid ethyl ester(113264-43-0)
• EPA Substance Registry System: 3-BroMo-2-oxo-pentanoic acid ethyl ester(113264-43-0)

Safety Data

• Hazardous Substances Data: 113264-43-0(Hazardous Substances Data)

Usage

General Description

3-Bromo-2-oxo-pentanoic acid ethyl ester is an organic compound with the chemical formula C7H11BrO3. It is a synthetic ester derived from 3-bromo-2-oxo-pentanoic acid, which is commonly used in organic synthesis and as a reagent in chemical reactions. 3-BroMo-2-oxo-pentanoic acid ethyl ester is a colorless liquid with a slightly sweet odor and is soluble in organic solvents. It is commonly used in the pharmaceutical industry as an intermediate in the synthesis of various drugs and compounds. Additionally, it is used in research and development processes for the production of new organic compounds and materials.

InChI:InChI=1/C7H11BrO3/c1-3-5(8)6(9)7(10)11-4-2/h5H,3-4H2,1-2H3

Upstream product

• 141-78-6 ethyl acetate 
• 1821-02-9 2-oxopentanoic acid 
• 88945-70-4 ethyl 2-hydroxy-n-valerate 
• 50461-74-0 ethyl 2-oxovalerate 

Downstream Products

• 796875-19-9 ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate 
• 1450603-82-3 C₁₇H₂₀FNO₄S 
• 1261181-00-3 ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate 
• 258346-46-2 5-ethyl-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylic acid 
• 113366-61-3 5-ethyl-2-phenylthiazole-4-carboxylic acid 
• 488115-57-7 5-ethyl-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester 
• 527384-54-9 ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate 
• 796875-20-2 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazole-4-carboxylic acid 

Relevant articles and documents

Discovery and mechanistic study of thiazole-4-acylsulfonamide derivatives as potent and orally active ChemR23 inhibitors with a long-acting effect in cynomolgus monkeys

Plasmacytoid dendritic cells (pDCs) are a subset of dendritic cells that can secrete large amounts of type I interferon. ChemR23, a G protein-coupled receptor (GPCR) expressed on the surface of pDCs, contributes to the recruitment of pDCs to inflamed tissues through chemotaxis signaling, and is therefore considered an attractive target for the treatment of autoimmune diseases. We previously reported benzoxazole-based compounds that can inhibit ChemR23 signaling through receptor internalization. Although these compounds showed ChemR23 internalization on pDCs in cynomolgus monkeys after oral administration, further improvement of the pharmacokinetics profile was needed for a clinical candidate and we therefore attempted scaffold-hopping from the benzoxazole core structure leading to novel thiazole derivatives. In this report, the design, synthesis, and biological evaluation of new thiazole-based ChemR23 inhibitors were described. Through sequential structure–activity relationship studies regarding (i) the side chain of the N-acylsulfonamide moiety, (ii) the 5-position of the thiazole ring, and (iii) the 1,2,4-oxadiazol-5-one moiety, we have succeeded in finding a potent thiazole-based ChemR23 inhibitor, 14f (IC80 = 12 nM). In addition, the oral administration of 14f at 30 mg/kg to cynomolgus monkeys demonstrated a sustained pharmacological effect of ChemR23 internalization on pDCs until 8 h after dosing, which was considered a longer effect in comparison to previously reported 2-aminobenzoxazole-based ChemR23 inhibitors. This report also shows the synthesis and evaluation of fluorescein-labeled compound 45c for a mechanistic study, and we could confirm the direct binding of our thiazole derivative to ChemR23. We believe that our research on small molecule ChemR23 inhibitors and chemical probe will contribute to the elucidation and analysis of the functions of ChemR23 as well as identifying novel therapeutics for autoimmune diseases.

Discovery, Synthesis and Evaluation of a Ketol-Acid Reductoisomerase Inhibitor

Ketol-acid reductoisomerase (KARI), the second enzyme in the branched-chain amino acid biosynthesis pathway, is a potential drug target for bacterial infections including Mycobacterium tuberculosis. Here, we have screened the Medicines for Malaria Venture Pathogen Box against purified M. tuberculosis (Mt) KARI and identified two compounds that have Ki values below 200 nm. In Mt cell susceptibility assays one of these compounds exhibited an IC50 value of 0.8 μm. Co-crystallization of this compound, 3-((methylsulfonyl)methyl)-2H-benzo[b][1,4]oxazin-2-one (MMV553002), in complex with Staphylococcus aureus KARI, which has 56 % identity with Mt KARI, NADPH and Mg2+ yielded a structure to 1.72 ? resolution. However, only a hydrolyzed product of the inhibitor (i.e. 3-(methylsulfonyl)-2-oxopropanic acid, missing the 2-aminophenol attachment) is observed in the active site. Surprisingly, Mt cell susceptibility assays showed that the 2-aminophenol product is largely responsible for the anti-TB activity of the parent compound. Thus, 3-(methylsulfonyl)-2-oxopropanic acid was identified as a potent KARI inhibitor that could be further explored as a potential biocidal agent and we have shown 2-aminophenol, as an anti-TB drug lead, especially given it has low toxicity against human cells. The study highlights that careful analysis of broad screening assays is required to correctly interpret cell-based activity data.

HETEROARYLTHIOMETHYL PYRIDINE DERIVATIVE

The present invention relates to a compound represented by a formula (I): wherein X is a group represented by or the like; Y is a group represented by or the like; and Ar1 is a group represented by or a pharmaceutically acceptable salt thereof.