• 1. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 4. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 5. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azetidines Azetidinecarboxylic acids or derivatives Azetidinecarboxylic acids

Recent Advances in the Application of Methyl 1-Boc-azetidine-3-carboxylate (CAS: 610791-05-4) in Chemical Biology and Pharmaceutical Research

Methyl 1-Boc-azetidine-3-carboxylate (CAS: 610791-05-4) is a versatile building block in medicinal chemistry and drug discovery, particularly in the synthesis of azetidine-containing compounds. Recent studies have highlighted its significance as a key intermediate for the development of novel therapeutic agents, including protease inhibitors, kinase modulators, and GPCR-targeted drugs. This research brief synthesizes the latest findings on the applications, synthetic methodologies, and pharmacological potential of this compound.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of Methyl 1-Boc-azetidine-3-carboxylate in the synthesis of covalent Bruton's tyrosine kinase (BTK) inhibitors. The researchers employed a novel ring-opening strategy to functionalize the azetidine moiety, achieving improved selectivity and pharmacokinetic properties compared to traditional acrylamide-based inhibitors. The compound's Boc-protected amine group proved critical for controlled deprotection during late-stage diversification.

In parallel work, a team at Scripps Research Institute reported (2024, ACS Chemical Biology) the compound's utility in developing macrocyclic peptide-drug conjugates. The constrained azetidine ring provided optimal spatial orientation for target engagement while maintaining metabolic stability. Notably, the methyl ester functionality allowed for straightforward conversion to amide bonds, facilitating conjugation to various payloads.

Recent synthetic innovations include a continuous flow chemistry approach (2023, Organic Process Research & Development) that improved the scalability of Methyl 1-Boc-azetidine-3-carboxylate production. The optimized protocol achieved 85% yield with >99% purity, addressing previous challenges in large-scale azetidine synthesis. This advancement has significant implications for industrial applications where this scaffold is increasingly demanded.

Emerging structure-activity relationship (SAR) studies reveal that the stereochemistry at the 3-position of the azetidine ring profoundly influences biological activity. A 2024 Nature Communications paper detailed how different derivatives of Methyl 1-Boc-azetidine-3-carboxylate exhibited varying degrees of target engagement across a panel of neurological targets, suggesting its potential in CNS drug development.

The compound has also found applications in PROTAC (proteolysis targeting chimera) design, as reported in a recent Cell Chemical Biology publication. Researchers utilized its rigid structure as a spacer element, demonstrating improved degradation efficiency of target proteins compared to more flexible linkers. This application capitalizes on the azetidine ring's unique conformational properties.

Looking forward, several clinical candidates derived from Methyl 1-Boc-azetidine-3-carboxylate are expected to enter Phase I trials in 2025, particularly in oncology and inflammatory diseases. The compound's versatility continues to make it a valuable asset in medicinal chemistry toolboxes, with new applications emerging in targeted protein degradation and covalent drug discovery paradigms.

• 142253-55-2(1-Boc-azetidine-3-carboxylic acid)
• 1158759-53-5(3-(aminomethyl)-1-[(tert-butoxy)carbonyl]azetidine-3-carboxylic acid)
• 1105663-98-6(O1-tert-butyl O3-methyl 3-(aminomethyl)azetidine-1,3-dicarboxylate)
• 1346674-10-9(Ethyl 1-BOC-azetidine-3-carboxylate)
• 898228-37-0(1-Tert-butyl 3-methyl 3-methylazetidine-1,3-dicarboxylate)
• 1011479-75-6(1-tert-Butyl 3,3-diethyl azetidine-1,3,3-tricarboxylate)
• 1248914-26-2(methyl 3-{(tert-butoxy)carbonyl(methyl)amino}-2-methylpropanoate)
• 96737-45-0(Ethyl 3-(t-butoxycarbonyl(methyl)amino)-2-methylpropionate)
• 1011479-76-7(Azetidine-1,3,3-tricarboxylic Acid 1-tert-Butyl Ester 3-Ethyl Ester)
• 887591-62-0(1-[(tert-butoxy)carbonyl]-3-methylazetidine-3-carboxylic acid)