57595-23-0

Basic information

• Product Name: Methyl 4-oxotetrahydrofuran-3-carboxylate
• Synonyms: 3-Furancarboxylic acid, tetrahydro-4-oxo-, methyl ester;Methyl 4-oxotetrahydrofuran-3-carboxylate;Methyl 4-oxotetrahydrofur...;Tetrahydro-4-oxo-3-furoic acid methyl ester;Tetrahydro-4-oxo-3-furancarboxylic Acid Methyl Ester;methyl 4-oxooxolane-3-carboxylate
• CAS NO: 57595-23-0
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.12532
• Mol File: 57595-23-0.mol

Chemical Properties

• Boiling Point: 220℃
• Flash Point: 91℃
• Appearance: /
• Density: 1.265
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.72±0.20(Predicted)
• CAS DataBase Reference: Methyl 4-oxotetrahydrofuran-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-oxotetrahydrofuran-3-carboxylate(57595-23-0)
• EPA Substance Registry System: Methyl 4-oxotetrahydrofuran-3-carboxylate(57595-23-0)

Safety Data

• RIDADR: UN1993
• Hazardous Substances Data: 57595-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-oxotetrahydrofuran-3-carboxylate is used as a key intermediate in the synthesis of fused-pyrimidine derivatives. These derivatives have been identified as a series of novel GPR119 agonists, which are potential therapeutic agents for the treatment of type 2 diabetes and obesity. Methyl 4-oxotetrahydrofuran-3-carboxylate plays a crucial role in the development of these new drugs by providing a versatile building block for the construction of the desired molecular structures.

Upstream product

• 623-50-7 ethyl 2-hydroxyacetate 
• 292638-85-8 acrylic acid methyl ester 
• 798541-68-1 methyl acrylate 
• 96-35-5 glycolic acid methyl ester 
• 158001-24-2 (±)-(tetrahydrofuran-3-yl)hydrazine hydrochloride 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 

Downstream Products

• 38983-99-2 2-(4-chloro-phenyl)-1,2,4,6-tetrahydro-furo[3,4-c]pyrazol-3-one 
• 127956-18-7 methyl 4-iodomethyl-3-phenylimino-tetrahydrofuran-4-carboxylate 
• 22929-52-8 tetrahydrofuran-3-one 

Relevant articles and documents

Synthesis method of tetrahydrofuran-3-ketone

The invention discloses a synthesis method of tetrahydrofuran-3-ketone. The method comprises the following steps of: under an alkaline condition, mixing glycolate (I) and acrylate (II) in a solvent, and carrying out condensation cyclization reaction to obtain 4-formic ester-tetrahydrofuran-3-ketone (III); then, under an acidic condition, performing reflux decarboxylation reaction on the 4-formic ester-tetrahydrofuran-3-ketone (III) so as to obtain thetetrahydrofuran-3-ketone (IV) . According to the synthesis method of the tetrahydrofuran-3-ketone, the yield is greater than 82%; and the method has the advantages of mild and easily-controlled conditions, mild reaction, simple and safe operation and environmental friendliness.

ISOXAZOLE CARBOXYLIC ACIDS AS LPA ANTAGONISTS

The present invention provides compounds of Formula (I) or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

TRIAZOLE CARBOXYLIC ACIDS AS LPA ANTAGONISTS

The present invention provides compounds of Formula (I), or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

Discovery of BNC375, a Potent, Selective, and Orally Available Type i Positive Allosteric Modulator of α7 nAChRs

Positive allosteric modulators (PAMs) of α7 nAChRs can have different properties with respect to their effects on channel kinetics. Type I PAMs amplify peak channel response to acetylcholine but do not appear to influence channel desensitization kinetics, whereas Type II PAMs both increase channel response and delay receptor desensitization. Both Type I and Type II PAMs are reported in literature, but there are limited reports describing their structure-kinetic profile relationships. Here, we report a novel class of compounds with either Type I or Type II behavior that can be tuned by the relative stereochemistry around the central cyclopropyl ring: for example, (R,R)-13 (BNC375) and its analogues with RR stereochemistry around the central cyclopropyl ring are Type I PAMs, whereas compounds in the same series with SS stereochemistry (e.g., (S,S)-13) are Type II PAMs as measured using patch-clamp electrophysiology. Further fine control over the kinetics has been achieved by changing the substitutions on the aniline ring: generally the substitution of aniline with strong electron withdrawing groups reduces the Type II character of these compounds. Our structure-activity optimization efforts have led to the discovery of BNC375, a small molecule with good CNS-drug like properties and clinical candidate potential.

(S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements and Structural and Biological Investigation

Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAR analysis. Interesting binding properties at GluA2, GluK1, and GluK3 receptors were discovered. The requirements for GluK3 interaction were elucidated by determining the X-ray structures of the GluK3-LBD with 2 and 5c and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

Discovery of Orally Bioavailable and Liver-Targeted Hypoxia-Inducible Factor Prolyl Hydroxylase (HIF-PHD) Inhibitors for the Treatment of Anemia

We report herein the design and synthesis of a series of orally active, liver-targeted hypoxia-inducible factor prolyl hydroxylase (HIF-PHD) inhibitors for the treatment of anemia. In order to mitigate the concerns for potential systemic side effects, we

INHIBITORS OF HIF PROLYL HYDROXYLASE

The present invention concerns compounds of formula I or pharmaceutically acceptable salts thereof, which inhibit HIF prolyl hydroxylase, their use for enhancing endogenous production of erythropoietin, and for treating conditions associated with reduced endogenous production of erythropoietin such as anemia and like conditions, as well as pharmaceutical compositions comprising such a compound and a pharmaceutical carrier.

INHIBITORS OF HIF PROLYL HYDROXYLASE

The present invention concerns compounds of formula I or a pharmaceutically acceptable salt thereof which inhibit HIF prolyl hydroxylase, their use for enhancing endogenous production of erythropoietin, and for treating conditions associated with reduced

Syntheses of tetrahydrothiophenes and tetrahydrofurans and studies of their derivatives as melanocortin-4 receptor ligands

Piperazinebenzylamine derivatives from trans-4-(4-chlorophenyl)tetrahydrothiophene-3-carboxylic acid 6 and its S-oxide 7 and sulfone 8, and the tetrahydrofuran 9 and its two regioisomers 11 and 13 were synthesized and studied for their binding affinities at the human melanocortin-4 receptor. These five-membered ring constrained compounds possessed similar or lower potency compared to the acyclic analogs.