Imidazole Derivatives as Important Building Blocks in Medicinal Chemistry and Technologies

Imidazole is an essential subunit in many natural compounds, marketed drugs, and synthetic materials [1]. Naturally occurring imidazoles are primarily represented by the so-called pyrrole-imidazole family of marine sponge alkaloids exhibiting an impressive diversity of structural motifs, all of which can be mapped back to their simplest member oroidine 1 (Fig.1) [2]. The imidazole ring is also present in the hormone histamine and amino acid histidine [3].

Applications of imidazoles in medicine are demonstrated by many commercialized drugs, such as tyrosine kinase inhibitor Nilotinib 3 and histamine receptor antagonist Cimetidine 2 (both depicted in Fig. 1) [4]. Different variations of synthetic pyrrole-imidazole polyamide arrays shown to be capable of detecting sequence-selective double-stranded DNA are now intensively investigated [5] as promising agents for the treatment of cancer and viral diseases. It should be pointed out that imidazoles are fundamental building blocks in many fields of technology. There are numerous reports on imidazole-based metal complexing agents [6], catalysts for ester hydrolysis [7], ionic liquids [8], and synthetic polymers [9]. Carboxyl-functionalized imidazoles were even used for metal nanoparticle surface engineering [10]. The imidazole-derived N-heterocyclic carbenes were employed as ligands to prepare catalysts for various metal-mediated reactions, e.g., olefin metathesis [11].

Figure 1. Examples of bioactive imidazole derivatives.

Life Chemicals is offering its proprietary collection of functionalized imidazoles. These compounds are well-suited as building blocks for drug discovery and organic synthesis. Several representatives are shown below:

Please, contact us at marketing@lifechemicals.com for any additional information and price quotations.

Visit our Website for a detailed product description, or place an order online on our E-commerce website.

Download SD files with compound structures directly from our Downloads section

The complete list of the related structures can be obtained upon request.

Further reading in our MedChem blog section dedicated to Building Blocks.

References

1. (a) Kerru, N.; Bhaskaruni, S. V. H. S.; Gummidi, L.; Maddila, S. N.; Maddila, S.; Jonnalagadda, S. B. Synth. Comm. 2019, 49, 2437-2459. (b) Xi, N.; Huang, Q.; Liu, L. in Comprehensive Heterocyclic Chemistry, 3rd edition, eds. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, and R. J.K. Taylor Pergamon, Oxford, 2008. Vol. 4, p. 143.
2. (a) Du, H.; He, Y.; Sivappa, R.; Lovely, C.J. Synlett 2006, 965. (b) Young, I. S.; Baran, P. S. Nat. Chem. 2009, 1, 193.
3. Berg, J.M.; Tymoczko, J.L.; Stryer, L. Biochemistry 5th ed. New York: W H Freeman; 2002.
4. According towww.drugbank.ca as of August 2019, 98 approved drugs are bearing the imidazole ring.
5. (a) Bando, T.; Sugiyama, H. Acc. Chem. Res. 2006, 39, 935. (b) Singh, I.; Wendeln, C.; Clark, A.W.; Cooper, J.M., Ravoo, B.J.; Burley, G.A. J. Am. Chem. Soc., 2013, 135, 3449.
6. Sun, D.; Yan, Z.-H.; Blatov, V.A.; Wang, L.; Sun, D.-F. Cryst. Growth & Design 2013, 13, 1277.
7. Orth, E.S.; Brandão, T.A.S.; Souza, B.S.; Pliego, J.R.; Vaz, B.G.; Eberlin, M.N.; Kirby, A.J.; Nome, F. J. Am. Chem. Soc. 2010, 132, 8513.
8. Green, M.D.; Long, T.E. J. Macromol. Sci. C: Polymer Rev. 2009, 49, 291.
9. Smith, T.W.; Zhao, M.; Yang, F.; Smith, D.; Cebe, P. Macromolecules, 2013, 46, 1133.
10. Bromberg, L.; Chen, L.; Chang, E.P.; Wang, S.; Hatton, A. Chem. Mater., 2010, 22, 5383.
11. Vougioukalakis, G.C.; Grubbs, R.H. Chem. Rev., 2010, 110, 1746.