• 1. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 2. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 3. Distribution pattern and allocation of defects in hydrogenated ZnO thin films?
  Vitaly Gurylev,Chung-Yi Su,Tsong-Pyng Perng Phys. Chem. Chem. Phys., 2016,18, 16033-16038
• 4. Excited state potential energy surfaces and their interactions in FeIVO active sites
  Shaun D. Wong,Edward I. Solomon Dalton Trans., 2014,43, 17567-17577
• 5. Estimation of hydrogen sulfide from crude petroleum: a unique invention using a simple chemosensor?
  Shampa Kundu,Prithidipa Sahoo New J. Chem., 2019,43, 12369-12374

Introduction to Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate (CAS No. 169457-73-2)

Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate, a compound with the chemical identifier CAS No. 169457-73-2, is a specialized organic molecule that has garnered significant attention in the field of pharmaceutical research and development. This compound belongs to the piperidine class of heterocyclic amines, which are widely recognized for their diverse biological activities and potential applications in medicinal chemistry. The unique structural features of Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate make it a valuable intermediate in the synthesis of various pharmacologically active agents.

The molecular structure of this compound consists of a piperidine ring substituted with a tert-butyl group at the 1-position and a 2-bromoethyl group at the 4-position. This arrangement imparts specific electronic and steric properties that can influence its reactivity and biological interactions. The presence of both bromine and tert-butyl groups provides multiple handles for further chemical modifications, making it an attractive scaffold for drug discovery programs.

In recent years, there has been growing interest in exploring the pharmacological potential of piperidine derivatives, particularly those with halogenated side chains. The bromine atom in Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate serves as a versatile handle for cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are widely employed in the construction of complex molecular architectures. These reactions are pivotal in the synthesis of novel drug candidates and have been extensively utilized in the development of small-molecule inhibitors targeting various disease pathways.

One of the most compelling aspects of Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate is its utility as a building block in the synthesis of G-protein coupled receptor (GPCR) modulators. GPCRs are integral membrane proteins that play a crucial role in cellular signaling and are implicated in numerous physiological processes. Modulating GPCR activity has emerged as a promising strategy for treating a wide range of disorders, including cardiovascular diseases, neurological disorders, and cancer. The piperidine core is a common pharmacophore in GPCR ligands, and modifications to this core can significantly alter receptor binding affinity and selectivity.

Recent studies have demonstrated that derivatives of piperidine can exhibit potent activity against various GPCRs by interacting with specific amino acid residues within the binding pocket. For instance, Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate has been investigated as a potential lead compound for developing novel antipsychotic agents. The combination of the tert-butyl group and the 2-bromoethyl side chain may confer favorable pharmacokinetic properties, such as improved solubility and metabolic stability, which are essential for successful drug development.

The synthesis of Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate typically involves multi-step organic transformations starting from commercially available precursors. Key steps include nucleophilic substitution reactions to introduce the bromoethyl group onto the piperidine ring, followed by protection-deprotection strategies to install the tert-butyl moiety at the appropriate position. Advanced synthetic techniques, such as transition-metal-catalyzed cross-coupling reactions, have been employed to achieve high yields and enantioselectivity in these processes.

The pharmaceutical industry has shown considerable interest in exploring the therapeutic potential of compounds like Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate. Preclinical studies have highlighted its ability to modulate neuronal signaling pathways, making it a candidate for treating conditions such as schizophrenia and depression. The unique structural features of this compound allow it to interact with multiple targets within neuronal circuits, potentially leading to synergistic effects that enhance therapeutic outcomes.

In addition to its applications in central nervous system (CNS) drug discovery, Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate has also been explored for its anti-inflammatory properties. Piperidine derivatives have been shown to inhibit inflammatory pathways by modulating key enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX). The presence of both bromine and tert-butyl groups may enhance binding affinity to these enzymes, leading to more potent anti-inflammatory effects.

The development of novel synthetic methodologies is crucial for optimizing the production of compounds like Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate. Continuous-flow chemistry has emerged as a powerful tool for improving reaction efficiency and scalability. By employing flow reactors, researchers can achieve higher reaction rates, better control over reaction conditions, and reduced byproduct formation. These advancements have significantly accelerated the synthesis process for complex molecules used in drug discovery.

The safety profile of Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate is another critical consideration in its application to pharmaceutical research. Extensive toxicological studies are conducted to assess its potential adverse effects on human health. These studies include evaluations of acute toxicity, chronic toxicity, genotoxicity, and carcinogenicity. Ensuring that compounds meet stringent safety standards is essential for their progression from preclinical to clinical development.

In conclusion, Tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate (CAS No. 169457-73-2) represents a promising candidate for further exploration in medicinal chemistry. Its unique structural features make it a versatile intermediate for synthesizing pharmacologically active agents targeting various diseases. Ongoing research continues to uncover new applications for this compound, highlighting its significance in advancing therapeutic strategies across multiple therapeutic areas.

• 2137707-25-4(tert-butyl 4-2-(bromomethyl)spiro3.3heptan-2-ylpiperidine-1-carboxylate)
• 193629-40-2(tert-butyl 3-(5-bromopentyl)piperidine-1-carboxylate)
• 1002359-91-2((R)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate)
• 210564-54-8(tert-Butyl 3-(2-bromoethyl)piperidine-1-carboxylate)
• 164149-27-3(tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylate)
• 158407-04-6(Tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate)
• 2172461-47-9(tert-butyl 1-(bromomethyl)-8-azaspiro4.5decane-8-carboxylate)
• 1363383-33-8(tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate)
• 142355-81-5(1-Boc-4-(4-Bromo-Butyl)-Piperidine)
• 193629-30-0(tert-Butyl 3-(3-bromopropyl)piperidine-1-carboxylate)