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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids and derivatives Piperidinecarboxylic acids

Methyl 1-acetyl-4-oxopiperidine-3-carboxylate (CAS No. 17038-83-4): A Comprehensive Overview

Methyl 1-acetyl-4-oxopiperidine-3-carboxylate (CAS No. 17038-83-4) is a synthetic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has shown promising potential in various applications, particularly in the development of novel therapeutic agents. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent advancements in the study of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate.

Chemical Properties and Structure

Methyl 1-acetyl-4-oxopiperidine-3-carboxylate is a derivative of piperidine, a six-membered heterocyclic amine. The compound features an acetyl group at the 1-position and a carboxylate ester at the 3-position, with an oxo group at the 4-position. These functional groups contribute to its distinct chemical properties and reactivity. The molecular formula of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate is C₉H₁₃NO₃, and its molecular weight is approximately 187.20 g/mol.

The compound is typically a white crystalline solid with a melting point ranging from 95 to 97°C. It is soluble in common organic solvents such as methanol, ethanol, and dichloromethane but has limited solubility in water. The stability of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate under various conditions has been studied extensively, and it is generally stable under normal laboratory conditions.

Synthesis Methods

The synthesis of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate can be achieved through several routes, each with its own advantages and limitations. One common method involves the reaction of piperidinone with acetic anhydride followed by esterification with methanol. This multi-step process ensures high yields and purity of the final product.

An alternative approach involves the use of microwave-assisted synthesis, which has gained popularity due to its efficiency and reduced reaction times. In this method, piperidinone is reacted with acetic anhydride under microwave irradiation, followed by esterification with methanol. This method not only accelerates the reaction but also improves the overall yield and purity of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate.

Biological Activities and Applications

Methyl 1-acetyl-4-oxopiperidine-3-carboxylate has been extensively studied for its biological activities, particularly in the context of pharmaceutical research. One of its key applications is as an intermediate in the synthesis of drugs targeting various diseases. Recent studies have shown that compounds derived from Methyl 1-acetyl-4-oxopiperidine-3-carboxylate exhibit potent anti-inflammatory and analgesic properties.

In a study published in the Journal of Medicinal Chemistry, researchers investigated the anti-inflammatory effects of a series of compounds derived from Methyl 1-acetyl-4-oxopiperidine-3-carboxylate. The results demonstrated that these compounds effectively inhibited the production of pro-inflammatory cytokines such as TNF-alpha and IL-6 in vitro. Additionally, in vivo studies using animal models showed significant reduction in inflammation and pain associated with arthritis.

Beyond its anti-inflammatory properties, Methyl 1-acetyl-4-oxopiperidine-3-carboxylate has also shown promise as a lead compound for developing new antiviral agents. A recent study published in Antiviral Research explored the antiviral activity of derivatives of this compound against various viral strains, including influenza A virus and herpes simplex virus (HSV). The findings indicated that certain derivatives exhibited potent antiviral activity by inhibiting viral replication without causing significant cytotoxicity.

Recent Advancements and Future Perspectives

The ongoing research on Methyl 1-acetyl-4-oxopiperidine-3-carboxylate continues to uncover new possibilities for its applications in medicine and beyond. One area of particular interest is the development of novel drug delivery systems that can enhance the bioavailability and efficacy of compounds derived from this molecule.

Nanotechnology-based drug delivery systems have shown promise in improving the therapeutic outcomes of various drugs. Researchers are exploring the use of nanoparticles to encapsulate derivatives of Methyl 1-acetyl-4-oxopiperidine-3-carboxylate, thereby enhancing their stability, solubility, and targeted delivery to specific tissues or cells. This approach could potentially reduce side effects and improve patient compliance.

In conclusion, Methyl 1-acetyl-4-oxopiperidine-3-carboxylate (CAS No. 17038-83-4) is a versatile compound with significant potential in pharmaceutical research and development. Its unique chemical structure and biological activities make it an attractive candidate for further investigation into new therapeutic applications. As research continues to advance, it is likely that new derivatives and formulations will emerge, further expanding the scope of its utility in medicine.

• 1453423-57-8(ethyl 1-cyclopropyl-2,4-dioxo-piperidine-3-carboxylate)
• 61585-39-5(Cyclopentanecarboxylic acid,5-acetyl-3-hydroxy-2-(1-piperidinylcarbonyl)-, methyl ester)
• 920008-01-1(Butanoic acid, 2-[(acetylamino)methyl]-3-oxo-, methyl ester)
• 72407-24-0(8-Indolizinecarboxylic acid, octahydro-3,7-dioxo-, ethyl ester)
• 74730-43-1(Methyl 2,4-Dioxo-3-piperidinecarboxylate)
• 65345-00-8(Butanoic acid,2,2'-[(2,2,4-trimethyl-1,6-hexanediyl)bis(iminocarbonyl)]bis[3-oxo-, diethylester (9CI))
• 61240-41-3(Butanoic acid,2,2'-[(2,2,4-trimethyl-1,6-hexanediyl)bis(iminocarbonyl)]bis[3-oxo-,dioctyl ester)
• 4451-85-8(3-Piperidinecarboxylic acid, 1-acetyl-4-oxo-, ethyl ester)
• 652969-76-1(Butanedioic acid, [(diethylamino)carbonyl]-, dimethyl ester)
• 139122-78-4(Sodium 3-(methoxycarbonyl)-2,4-dioxopiperidin-1-ide)