2-Azetidinone

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Cat Number

INT930212

CAS Number

930-21-2

For research use only. We do not supply to patients.

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Product Detail Description Scientific Support Customer Q&A

CAS Number

930-21-2

Storage

2-8℃

Synonyms

AZETIDIN-2-ONE

Molecular Formula

C3H5NO

Molecular Weight

71.08

Smiles

N1CCC1=O

Appearance

Clear colorless liquid

Melting Point

75℃

Boiling Point

106℃

Relative Density

1.03

General Description

2-Azetidinone (also known as beta-propiolactam) is the simplest four-membered lactam — a beta-lactam ring consisting of a nitrogen atom and three carbon atoms in a cyclic amide configuration. As the unsubstituted parent of the beta-lactam antibiotic family (penicillins, cephalosporins, carbapenems), 2-azetidinone serves as the fundamental building block for understanding beta-lactam chemistry and as a precursor for the synthesis of more complex beta-lactam derivatives.

Mechanism of Action

2-Azetidinone functions as the basic beta-lactam scaffold in medicinal chemistry. The strained four-membered ring (which confers the characteristic biological activity of beta-lactam antibiotics) is the key structural feature. The amide nitrogen and carbonyl of the azetidinone ring are the pharmacophoric elements that inhibit bacterial D,D-transpeptidases (penicillin-binding proteins, PBPs) by forming a stable acyl-enzyme complex, preventing bacterial cell wall cross-linking. The ring strain (~20 kcal/mol) drives the reaction with the enzyme active site serine.

Application

2-Azetidinone is used as a research intermediate in beta-lactam antibiotic synthesis, including the synthesis of monocyclic beta-lactam (aztreonam) analogs, penem derivatives, and carbapenem precursors. The beta-lactam ring is the defining structural feature of one of the most important antibiotic classes in clinical use. Modified azetidinone derivatives are also being investigated as serine protease inhibitors and in the development of anti-inflammatory agents.

2-Azetidinone (β-lactam) is a four-membered heterocyclic core structure of numerous antibiotics including penicillins and cephalosporins. Recent research has revealed its broad pharmacological potential beyond antibacterial activity. The Staudinger ketene-imine cycloaddition is the primary synthetic method. Substitutions at different positions generate diverse activities: C3 and C4 modifications yield cholesterol absorption inhibitors, anti-inflammatory, antitumor, anti-HIV, and antiparkinsonian agents; N1-activation produces enzyme inhibitors targeting human leukocyte elastase, tryptase, thrombin, and HCMV protease. Additional derivatives exhibit antitubercular, antidiabetic (PPAR agonists), vasopressin V1a antagonist, and anticonvulsant activities. The 2-azetidinone scaffold offers high structural versatility and multiple target interactions, making it a privileged structure in medicinal chemistry with promising applications in cardiovascular diseases, inflammation, oncology, and neurological disorders.

Fig. 1 Synthesis of 2-Azetidinone derivatives. (Mehta P D.; et al. 2010)

References

Mehta P D, et al. 2-Azetidinone–a new profile of various pharmacological activities. European journal of medicinal chemistry, 2010, 45(12): 5541-5560.

What is the recommended storage condition for 2-Azetidinone?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 2-Azetidinone?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What analytical characterization data is available for 2-Azetidinone?

Standard analytical data including HPLC purity profile, NMR confirmation, and physical specifications are included in the COA. Additional characterization data can be arranged upon request.

What functional groups in 2-Azetidinone are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Is 2-Azetidinone manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.