C-Substituted Azepanes for Novel Organic Synthesis and Drug Discovery Research

Our Unique Building Blocks to Perform Far and Wide
12 November 2020
Oleg Lukin
Senior Research Scientist

On account of their continuing pharmacological significance azepane ring containing structures attract considerable attention in organic synthesis and drug discovery.1-2

There are several naturally occurring azepane derivatives possessing a number of biological activities. For example, azepane ring containing metabolite (-)-balanol 13 (Figure 1) showed the potency as an ATP-competitive inhibitor of the protein kinase. This natural compound has since been used as a scaffold for development of a series of analogues as potential antitumor agents.4 Presently there are 5 approved and ca. 20 experimental drugs that have the azepane substructure.5 Among them, Tolazamide 2 is an oral blood glucose lowering drug used for people with type 2 diabetes. Another azepane containing marketed drug Azelastine 3 represents an example of a potent, second-generation, selective histamine antagonist.

Noteworthy, substituted azepanes have flexible ring structures and this conformational diversity is often decisive for their bioactivity.6 Therefore, the ability to introduce specific substituents into the azepane ring to bias it to one major conformation is important for effective drug design.

Examples of bioactive azepane-ring containing compounds

Figure 1. Examples of bioactive azepane-ring containing compounds

The full list of the functionalized azepanes offered by Life Chemicals can be obtained upon request at orders@lifechemicals.com. Please see some representative compounds below:

Representative functionalized azepanes by Life Chemicals


  1. (a) Barbero, A.; Diez-Varga, A.; Pulido, F. J.; González-Ortega, A.Org. Lett. 2016, 18, 1972–1975. (b) Zhou, J.; Yeung, Y.-Y. Org. Lett. 2014, 16, 2134–2137.
  2. Bremner, J. B.;Samosorn, S. In Comprehensive Heterocyclic Chemistry III, Eds. Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. Pergamon, Oxford, 2008. Vol. 13, p. 1.
  3. Kulanthaivel, P.; Hallock, Y.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452.
  4. Breitenlechner, C. B.; Friebe, W. G.; Brunet, E.; Werner, G.; Graul, K.; Thomas, U.; Kunkele, K. P.; Schafer, W.; Gassel, M. Bossemeyer, D.; Huber, R.; Engh, R. A.; Masjost, B.; J. Med. Chem. 2005, 48, 163.
  5. www.drugbank.ca; accessed in March 2019.
  6. (a) Patel, A. R.; Liu, F. Tetrahedron 2013, 69, 744–752. (b) Patel, A. R.; Ball, G.; Hunter, L.; Liu, F. Org. Biomol.
12 November 2020, 12:19 Oleg Lukin Building Blocks

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