Potential anticancer activity of 16 azetidin-2-one derivatives was evaluated showing that compound [-(-methoxy-phenyl)-2-(-methyl-phenyl)-3-phenoxy-azetidin-2-one] presented cytotoxic activity in SiHa cells and B16F10 cells. The caspase-3 assay in B16F10 cells displayed that azetidin-2-one derivatives induce apoptosis. Microarray and molecular analysis showed that compound was involved on specific gene overexpression of cytoskeleton regulation and apoptosis due to the inhibition of some cell cycle genes. From the 16 derivatives, compound showed the highest selectivity to neoplastic cells, it was an inducer of apoptosis, and according to an analysis of chemical interactions with colchicine binding site of human α/β-tubulin, the mechanism of action could be a molecular interaction involving the amino acids outlining such binding site.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238468PMC
http://dx.doi.org/10.1021/acsmedchemlett.6b00313DOI Listing

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Article Synopsis
  • - Spiro-heterocycles are significant in medicinal chemistry due to their potential biological effects and therapeutic properties.
  • - Various synthetic methods have been developed over the years to create these spirocyclic compounds, such as spiro-azetidin-2-one and spiro-pyrrolidine.
  • - This review focuses on the key synthetic strategies for producing these spiro heterocycles, particularly those established in the last two decades.
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The application of hydrazones and hydrazide-hydrazones in the synthesis of bioactive azetidin-2-one derivatives: A mini review.

Biomed Pharmacother

July 2023

Chair and Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland. Electronic address:

The hydrazones and hydrazide-hydrazones beside possessing crucial bioactivity can serve as useful intermediates in the synthesis of heterocyclic systems like 1,3-benzothiazin-4-one, 1,3-thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives. The azetidin-2-one derivatives show mainly antibacterial, antitubercular and antifungal activity as well as anti-inflammatory, antioxidant, anticonvulsant and antidepressant activity and activity against Parkinson's disease. This review is focused on the literature reports which consider the synthesis and biological properties of azetidin-2-one derivatives.

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By exploiting the ample biological potential of 1,3,4-oxadiazole/thiadiazole ring, 4-substitutedphenyl-1,3,4-oxadiazol/Thiadiazol-2-yl)-4-(4-substitutedphenyl) azetidin-2-one derivatives were prepared. Various substituted azetidin-2-one derivatives have been identified as immunostimulating and antimicrobial, as well as their antioxidant activity. 2-amino 1,3,4 oxadiazole/thiadiazole conjugates were synthesized by mixing semi/thio carbazides and sodium acetate with water and stirring well, followed by adding aldehydes in methanol at room temperature.

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Monocyclic ß-lactams (azetidin-2-ones) exhibit a wide range of biological activities, the most important of which are antibacterial, anticancer, and cholesterol absorption inhibitory activities. The synthesis of decorated monocyclic ß-lactams is challenging because their ring is highly constrained and consequently reactive, which is also an important determinant of their biological activity. We present the optimized synthesis of orthogonally protected 3-amino-4-substituted monocyclic ß-lactams.

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Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), a contemporary coronavirus, has impacted global economic activity and has a high transmission rate. As a result of the virus's severe medical effects, developing effective vaccinations is vital. Plant-derived metabolites have been discovered as potential SARS-CoV-2 inhibitors.

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