1,3-Diazetidin-2-Ones: Synthetic Approaches and Therapeutic Promise within the Aza-β-Lactam Family

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F25%3A00642307" target="_blank" >RIV/61389030:_____/25:00642307 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/25:73632453

Výsledek na webu

<a href="https://doi.org/10.1002/ejoc.202500747" target="_blank" >https://doi.org/10.1002/ejoc.202500747</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.202500747" target="_blank" >10.1002/ejoc.202500747</a>

Jazyk výsledku

angličtina

Název v původním jazyce

1,3-Diazetidin-2-Ones: Synthetic Approaches and Therapeutic Promise within the Aza-β-Lactam Family

Popis výsledku v původním jazyce

1,3-diazetidin-2-ones, overlooked members of the aza-beta-lactam family, are structurally distinct four-membered nitrogen-containing heterocycles with strong potential in medicinal chemistry, particularly as beta-lactamase inhibitors and antibiotic analogues. This review provides a comprehensive overview of their synthesis, structural diversity, and biological significance. The most established synthetic method is the [2 + 2] cycloaddition between C=N nucleophiles and isocyanates, though this approach is highly substrate dependent and frequently leads to side products or cycloreversion. Alternative strategies-including photochemical and organometallic methodologies-have been explored but remain limited in scope. As a result, access to 1,3-diazetidin-2-ones is significantly constrained, impeding wider investigation and application. In silico studies suggest favorable stability and reactivity profiles and indicate these compounds could circumvent beta-lactam resistance through hydrolysis-resistant enzyme intermediates. Several derivatives have demonstrated promising antibacterial, antifungal, antioxidant, and anticancer activities. Nevertheless, further synthetic innovation is essential to fully realize the therapeutic potential of this underexplored class of heterocycles.

Název v anglickém jazyce

1,3-Diazetidin-2-Ones: Synthetic Approaches and Therapeutic Promise within the Aza-β-Lactam Family

Popis výsledku anglicky

1,3-diazetidin-2-ones, overlooked members of the aza-beta-lactam family, are structurally distinct four-membered nitrogen-containing heterocycles with strong potential in medicinal chemistry, particularly as beta-lactamase inhibitors and antibiotic analogues. This review provides a comprehensive overview of their synthesis, structural diversity, and biological significance. The most established synthetic method is the [2 + 2] cycloaddition between C=N nucleophiles and isocyanates, though this approach is highly substrate dependent and frequently leads to side products or cycloreversion. Alternative strategies-including photochemical and organometallic methodologies-have been explored but remain limited in scope. As a result, access to 1,3-diazetidin-2-ones is significantly constrained, impeding wider investigation and application. In silico studies suggest favorable stability and reactivity profiles and indicate these compounds could circumvent beta-lactam resistance through hydrolysis-resistant enzyme intermediates. Several derivatives have demonstrated promising antibacterial, antifungal, antioxidant, and anticancer activities. Nevertheless, further synthetic innovation is essential to fully realize the therapeutic potential of this underexplored class of heterocycles.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EH23_020%2F0008497" target="_blank" >EH23_020/0008497: SMART rostlinné biotechnologie pro udržitelné zemědělství</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

1099-0690

Svazek periodika

28

Číslo periodika v rámci svazku

43

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

17

Strana od-do

e202500747

Kód UT WoS článku

001578383500001

EID výsledku v databázi Scopus

2-s2.0-105017091284