1228675-25-9

Usage

Uses

Used in Pharmaceutical Research:
4-Benzyl 1-Tert-Butyl 2-Oxopiperazine-1,4-Dicarboxylate is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential therapeutic applications. Its unique structure allows for the development of new drugs with improved efficacy and safety profiles.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Benzyl 1-Tert-Butyl 2-Oxopiperazine-1,4-Dicarboxylate serves as a versatile building block for the creation of complex organic molecules. Its functional groups enable various chemical reactions, facilitating the synthesis of a wide range of organic compounds.
Used in the Development of Antipsychotic Agents:
4-Benzyl 1-Tert-Butyl 2-Oxopiperazine-1,4-Dicarboxylate and its derivatives are used as active pharmaceutical ingredients in the development of antipsychotic agents. Their potential to modulate neurotransmitter systems and exhibit neuroprotective effects make them valuable in the treatment of psychiatric disorders.
Used in Medicinal Chemistry:
In medicinal chemistry, 4-Benzyl 1-Tert-Butyl 2-Oxopiperazine-1,4-Dicarboxylate is utilized for the design and optimization of novel drug candidates. Its structural features allow for the fine-tuning of pharmacokinetic and pharmacodynamic properties, leading to the discovery of more effective and safer therapeutic agents.
Overall, 4-Benzyl 1-Tert-Butyl 2-Oxopiperazine-1,4-Dicarboxylate is a multifaceted chemical compound with significant applications across various scientific disciplines, particularly in the realm of pharmaceuticals and organic synthesis. Its potential for therapeutic use, especially in antipsychotic drug development, highlights its importance in advancing modern medicine.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 78818-15-2 4-benzyloxycarbonylpiperazin-2-one 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1228675-26-0 4-benzyl 1-tert-butyl 2-hydroxypiperazine-1,4-dicarboxylate 
• 1361224-49-8 benzyl (2-((tert-butoxycarbonyl)amino)ethyl)(2-oxo-3-pentyn-1-yl)-carbamate 
• 1361224-50-1 benzyl 3-(propan-1-yn-1-yl)piperazine-1-carboxylate 
• 1361224-51-2 benzyl 3-(1-propyn-1-yl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-phenyl)-1-piperazinecarboxylate 
• 1450621-44-9 benzyl (2-((tert-butoxycarbonyl)amino)ethyl)(4-methyl-2-oxo-3-penten-1-yl)carbamate 
• 1450621-66-5 benzyl (2-((tert-butoxycarbonyl)amino)ethyl)(5-((tert-butyl(diphenyl)silyl)oxy)-2-oxo-3-pentyn-1-yl)carbamate 
• 1589534-93-9 benzyl (3S)-4-(4-(methylcarbamoyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1589534-88-2 benzyl (3S)-4-phenyl-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1589535-34-1 benzyl 3-(1-propyn-1-yl)-4-(5-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-1,3-thiazol-2-yl)-1-piperazinecarboxylate 
• 1589535-33-0 benzyl 4-(5-acetyl-1,3-thiazol-2-yl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1589535-32-9 benzyl 4-(5-(methoxy(methyl)carbamoyl)-1,3-thiazol-2-yl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1589535-03-4 benzyl 4-(4-(methylsulfonyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1589534-98-4 benzyl (3S)-4-(4-(phenylsulfamoyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 
• 1572928-06-3 benzyl (3S)-4-(4-((cyclopropylmethyl)-sulfamoyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinecarboxylate 

Relevant academic research and scientific papers

Novel RET inhibitors. Pharmaceutical composition and use thereof

The invention belongs to the field of medicines, and relates to a novel RET inhibitor, a pharmaceutical composition and application thereof. , The present invention relates to a compound represented by formula (I), a stereoisomer, a tautomer, an oxynitrid

A Straightforward Synthesis of Six-Membered-Ring Heterocyclic α-Aminophosphonic Acids from N-Acyliminium Ions

A convenient synthesis of phosphonic analogues of pipecolic acid and its heterocyclic analogues is reported. The major step of the elaborated procedure is the introduction of the phosphonate group into the skeleton of the appropriate cyclic amide through N-acyliminium ions. The former ones were obtained by preparation of the hemiaminals or their methyl ethers from the N-protected cyclic amides. Finally, the reaction with trimethyl phosphite in the presence of BF3·OEt2 afforded the desired phosphonates, which were converted into phosphonic acids by the hydrolysis of phosphonate moiety with simultaneous cleavage of the nitrogen protecting groups.

Small molecule disruptors of the Glucokinase-Glucokinase regulatory protein interaction: 2. Leveraging structure-based drug design to identify analogues with improved pharmacokinetic profiles

In the previous report, we described the discovery and optimization of novel small molecule disruptors of the GK-GKRP interaction culminating in the identification of 1 (AMG-1694). Although this analogue possessed excellent in vitro potency and was a useful tool compound in initial proof-of-concept experiments, high metabolic turnover limited its advancement. Guided by a combination of metabolite identification and structure-based design, we have successfully discovered a potent and metabolically stable GK-GKRP disruptor (27, AMG-3969). When administered to db/db mice, this compound demonstrated a robust pharmacodynamic response (GK translocation) as well as statistically significant dose-dependent reductions in fed blood glucose levels.

TRICYCLIC ALKYNES THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN

The present invention relates to tricyclic alkyne compounds of formula I that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where gluco

Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N′-arylpiperazine series

We have recently reported a novel approach to increase cytosolic glucokinase (GK) levels through the binding of a small molecule to its endogenous inhibitor, glucokinase regulatory protein (GKRP) these initial investigations culminated in the identification of 2-(4-((2S)-4-((6-amino-3- pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3, 3-hexafluoro-2-propanol (1, AMG-3969), a compound that effectively enhanced GK translocation and reduced blood glucose levels in diabetic animals. Herein we report the results of our expanded SAR investigations that focused on modifications to the aryl carbinol group of this series. Guided by the X-ray cocrystal structure of compound 1 bound to hGKRP, we identified several potent GK-GKRP disruptors bearing a diverse set of functionalities in the aryl carbinol region. Among them, sulfoximine and pyridinyl derivatives 24 and 29 possessed excellent potency as well as favorable PK properties. When dosed orally in db/db mice, both compounds significantly lowered fed blood glucose levels (up to 58%).

SULFONYL COMPOUNDS THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN

The present invention relates to sulfonyl compounds that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

Antidiabetic effects of glucokinase regulatory protein small-molecule disruptors

Glucose homeostasis is a vital and complex process, and its disruption can cause hyperglycaemia and type II diabetes mellitus. Glucokinase (GK), a key enzyme that regulates glucose homeostasis, converts glucose to glucose-6-phosphate in pancreatic β-cells, liver hepatocytes, specific hypothalamic neurons, and gut enterocytes. In hepatocytes, GK regulates glucose uptake and glycogen synthesis, suppresses glucose production, and is subject to the endogenous inhibitor GK regulatory protein (GKRP). During fasting, GKRP binds, inactivates and sequesters GK in the nucleus, which removes GK from the gluconeogenic process and prevents a futile cycle of glucose phosphorylation. Compounds that directly hyperactivate GK (GK activators) lower blood glucose levels and are being evaluated clinically as potential therapeutics for the treatment of type II diabetes mellitus. However, initial reports indicate that an increased risk of hypoglycaemia is associated with some GK activators. To mitigate the risk of hypoglycaemia, we sought to increase GK activity by blocking GKRP. Here we describe the identification of two potent small-molecule GK-GKRP disruptors (AMG-1694 and AMG-3969) that normalized blood glucose levels in several rodent models of diabetes. These compounds potently reversed the inhibitory effect of GKRP on GK activity and promoted GK translocation both in vitro (isolated hepatocytes) and in vivo (liver). A co-crystal structure of full-length human GKRP in complex with AMG-1694 revealed a previously unknown binding pocket in GKRP distinct from that of the phosphofructose-binding site. Furthermore, with AMG-1694 and AMG-3969 (but not GK activators), blood glucose lowering was restricted to diabetic and not normoglycaemic animals. These findings exploit a new cellular mechanism for lowering blood glucose levels with reduced potential for hypoglycaemic risk in patients with type II diabetes mellitus.

SULFONYLPIPERAZINE DERIVATIVES THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN FOR THE TREATMENT OF DIABETES

The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

Substituted 2,5-diazabicyclo[4.1.0]heptanes and their application as general piperazine surrogates: synthesis and biological activity of a Ciprofloxacin analogue

Piperazines and modified piperazines, such as homopiperazines and 2-methylpiperazines, are found in a wide range of pharmaceutical substances and biologically active molecules. In this study 2,5-diazabicyclo[4.1.0]heptanes, in which a cyclopropane ring is