(1R,2S,5R)-7-Oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
[CAS# 1192651-49-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: (1R,2S,5R)-7-Oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• Synonyms: (2S,5R)-7-oxo-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• Molecular Formula: C₁₄H₁₇N₃O₃
• Molecular Weight: 275.30
• CAS Registry Number: 1192651-49-2
• EC Number: 812-287-7
• SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OCC3=CC=CC=C3)C(=O)N

Properties

• Solubility: Very slightly soluble (0.44 g/L) (25 °C), Calc.^*
• Density: 1.36±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.643, Calc.^*
• Boiling Point: 543.6±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 282.6±24.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H228-H315-H319
• Safety Statements: P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313
• Transport Information: UN 1325

Discovery and Applications

The compound (1R,2S,5R)-7-oxo-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is a synthetic derivative of the diazabicyclooctane (DABCO) family, which is known for its rigid and unique bicyclic structure. This particular compound has a benzyl ether (benzyloxy) group and a carboxamide functional group on the diazabicyclooctane backbone. The discovery of this compound stems from research efforts aimed at developing novel scaffolds for pharmaceutical applications, taking advantage of the unique structural features of DABCO derivatives to create compounds with enhanced biological activity and chemical stability.

The main application of (1R,2S,5R)-7-oxo-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is in the development of antibacterial agents. The rigid DABCO framework combined with the carboxamide and benzyloxy functional groups contributes to its ability to inhibit bacterial enzymes and disrupt bacterial cell wall synthesis. This makes it a potential candidate for the treatment of bacterial infections, especially those caused by drug-resistant strains.

The compound can be used as a scaffold for the design of enzyme inhibitors, especially for enzymes involved in disease pathways. The DABCO core provides a stable platform, while the carboxamide and benzyloxy groups can be modified to interact with specific active sites of enzymes. This application is valuable in drug discovery and development of inhibitors that can modulate enzyme activity in diseases such as cancer, diabetes, and neurodegenerative diseases.

In drug development, (1R,2S,5R)-7-oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is explored for its potential as a lead compound or intermediate in the synthesis of novel therapeutic agents. Its unique structure allows for the attachment of various functional groups, enabling the creation of a variety of chemical libraries for screening biological targets. This versatility helps identify new drugs with improved pharmacological properties.

The compound is used in structural biology studies to investigate protein-ligand interactions. Its well-defined structure and functional group allow it to interact with proteins in a predictable manner, making it a useful tool for elucidating binding mechanisms and guiding the design of new ligands and inhibitors. This application is essential for understanding the molecular basis of protein function and rational drug design.

In organic synthesis, (1R,2S,5R)-7-oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is used as a building block for the construction of complex molecules. Its rigid and versatile structure allows the introduction of a variety of substituents, facilitating the synthesis of a wide range of chemical entities, thus supporting the development of new synthetic methods and the exploration of new chemical space.

The compound's potential to interact with biomolecules also makes it valuable in chemical biology studies. It can be used as a probe to study cellular processes, understand disease mechanisms, and identify potential therapeutic targets. Its ability to interact with proteins and other biomacromolecules provides insights into molecular recognition and signal transduction pathways.

References

2016. Manufacturing Route to Avibactam. Synfacts.
DOI: 10.1055/s-0036-1589739

2016. Avibactam. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0210