Substituted Azetidines in Drug Discovery

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12 April 2022
Oleg Lukin
Senior Research Scientist

Azetidines are an important class of aza-heterocyclic compounds with remarkable biological activities [1]. Among those, azetidine-2-ones (β-lactams) have attracted the greatest interest owing to their key role in antibacterial activity [2]. Presently, ca. 60 approved and over 30 experimental drugs bear the moiety of azetidine-2-one [3]. Notably, the unit of azetidine in the majority of commercial drugs is usually condensed to a different cycle, as exemplified by Cefotiam 1 in Figure 1. A monocyclic azetidine-2-one, like the one present in Ezetimibe 2, is not commonly present in azetidine-based medications. Today the azetidine ring finds a wider application as a pharmacological tool in many bioactive compounds, usually in HTS [4] and the medicinal chemistry structure-activity studies [5]. For example, a combination of the azetidine ring with a quinolone nucleus yielded compounds of type 3 [6] (Figure 1) exhibiting superior antibacterial activity against quinolone-susceptible MRSA in comparison to clinically used fluoroquinolones, such as levofloxacin and gatifloxacin. Compound 4 gives an example of an easily accessible azetidine-based inhibitor of N-ribosyl hydrolases and phosphorylases with potential utility as a drug candidate [7].

Figure 1. Examples of important azetidine-based compounds

At Life Chemicals, we offer our proprietary collection of functionalized azetidines. These compounds are well suited for use in drug discovery and organic synthesis. Several representatives are shown below. 

The compound selection can be customized based on your requirements, cherry picking is available.

Please, contact us at for any additional information and price quotations.


  1. (a) Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988–4035. (b) Maetani, M.; Zoller, J.; Melillo, B.; Verho, O.; Kato, N.; Pu, J.; Comer, E.; Schreiber, S. L. J. Am. Chem. Soc. 2017, 139, 11300–11306.
  2. Singh, G. S.; D’ghooghe, M.; De Kimpe, N. In Comprehensive Heterocyclic Chemistry III, Eds. Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. Pergamon, Oxford, 2008. Vol. 2, p. 3.
  3.; accessed in May 2019.
  4. Lowe, J. T.; Lee IV, M. D.; Akella, L. B. et al. J. Org. Chem. 2012, 77, 7187–7211.
  5. For selected recent reports on bioactive compounds containing the azetidine ring, see: (a) Yu, L.-F.; Eaton, J. B.; Fedolak, A.; Zhang, H.-K.; Hanania, T.; Brunner, D.; Lukas, R. J.; Kozikowski, A. P. J. Med. Chem. 2012, 55, 9998–10009. (b) Han, Y.; Han, M.; Shin, D.; Song, C.; Hahn, H.-J. J. Med. Chem. 2012, 55, 8188–8192. (c) Honcharenko, D.; Barman, J.; Varghese, O. P.; Chattopadhyaya, J. Biochemistry 2007, 46, 5635. (d) Slade, J.; Bajwa, J.; Liu, H.; Parker, D.; Vivelo, J.; Chen, G. P.; Calienni, J.; Villhauer, E.; Prasad, K.; Repic, O.; Blacklock, T. J. Org. Process Res. Dev. 2007, 11, 825.
  6. Ikee, Y.; Hashimoto, K.; Nakashima, M.; Hayashi, K.; Sano, S.; Shiro, M.; Nagao, Y. Bioorg. Med. Chem. Lett. 2007, 17, 942.
  7. Evans, G. B.; Fumeaux, R. H.; Greatrex, B.; Murkin, A. S.; Schramm, V. L.; Tyler, P. C. J. Med. Chem. 2008, 51, 948.
12 April 2022, 16:35 Oleg Lukin Building Blocks

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