Bioactive Compounds and Materials Based on Functionalized 1,3,4-Oxadiazoles

It is generally known that 1,3,4-oxadiazole is one of the most versatile heterocyclic compounds [1]. A number of the 1,3,4-oxadiazoles have shown a very broad spectrum of biological activity [2], e.g., anti-cancer activity [3], inhibitors of various enzymes [4], herbicides [5], antifungal activity [6], etc.

The already launched drug Raltegravir 1 [7], the drug candidate at the late-stage of clinical development, Zbotentan 2 [8], and the marketed herbicide Methoxydiazone 3 (Fig. 1) bearing a structural unit of 1,3,4-oxadiazole do nicely illustrate the potential of the heterocycle in drug discovery and agriculture.

Furthermore, the 1,3,4-oxadiazoles have also been widely used to create novel materials. For example, there are 1,3,4-oxadiazole-based heat-resistant polymers [9], electron-transporting and blue-light-emitting polymers (e.g., polymer 4 in Fig. 1) [10], dendrimers [11], extremely effective laser dyes [12], and metallo-mesogens [13].

Additionally, the 1,3,4-oxadiazoles have been used in organic synthesis for the generation of carbenes to react with electrophilic functionalities [14]. Yet another promising synthetic application of the 1,3,4-oxadiazoles is their tandem intramolecular [4+2]/[3+2] cycloaddition cascade [15].

Figure 1. Examples of 1,3,4-oxadiazole-based bioactive compounds and materials

These low-molecular-weight reagents are well suited for application in drug discovery and organic synthesis, with some of their representatives being shown below.

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References

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2. Yogesh, M.; Senthilkumar, G. P. World J. Pharmaceut. Res. 2019, 8, 1406-1428.
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5. Das, A.C.; Debnath, A.; Mukherjee, D. Chemosphere 2003, 53, 217.
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8. James, N. D.; Growcott, J. W. Drugs Future 2009, 34, 624.
9. Hill, J. in Comprehensive Heterocyclic Chemistry, 2nd edition, eds. A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 4, p. 268.
10. Ding, J.; Day, M.; Robertson, G.; Roovers, J. Macromolecules 2002, 35, 3474.
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13. Wen, C.-R.; Wang, Y.-J.; Wang, H.-C.; Sheu, H.-S.; Lee, G.-H.; Lai, C.K. Chem. Mater. 2005, 17, 1646.
14. Warkentin, J.; Acc. Chem. Res. 2009, 42, 205.
15. Elliott, G.I.; Fuchs, J.R.; Blagg, B.S.J.; Ishikawa, H.; Tao, H.; Yuan, Z.-Q.; Boger, D.L. J. Am. Chem. Soc. 2006, 128, 10589.