Expand Your Building Block Collection with Our Functionalized 1,3-Oxazoles

Although the parent 1,3-oxazole¹ is not naturally occurring, a large number of substituted oxazole-containing natural products have been isolated, mostly from marine microorganisms.² Many of these natural products are structurally complex (for example, cyclic peptide Leucamide A 1³ (depicted in Fig. 1) and of considerable biological interest. Attempts at the total synthesis⁴ of naturally occurring derivatives have recently driven many of the discoveries of original oxazole chemistry.

On account of their versatile biological activities, oxazoles have found their use in medicine.⁵ Besides a few commercialized drugs, such as Oxaprozin 2 and Sulfamoxole 3 (Fig. 1), there are ca. 30 exploratory and advanced drug candidates containing the oxazole fragment.⁶ In organic chemistry oxazoles and their derivatives have been used as azadienes in Diels–Alder reactions⁷ and as ligands for asymmetric catalysts (e.g., compound 4 in Fig. 1).⁸

Figure 1. On the relevance of the 1,3-oxazole fragment

We offer diversely functionalized 1,3-oxazoles for your research. Several representative title structures available from Life Chemicals are listed below. The full list of the functionalized 1,3-oxazoles is available upon request at orders@lifechemicals.com.

 References:

1. (a) Yeh, V.; Iyengar, R. 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. 487. (b) Slobodyanyuk, E. Yu.; Volochnyuk, D. M. Chem. Heterocycl. Compounds 2019, 55, 202-204.
2. Jin, Z. Nat. Prod. Rep. 2011, 28, 1143.
3. König, G. M.; Kehraus, S.; Seibert, S. F.; Abdel-Lateff, A.; Müller, D. ChemBioChem 2006, 7, 229.
4. Wang, B.; Hansen, T.M.; Weyer, L.; Wu, D.; Wang, T.; Christmann, M.; Lu, Y.; Ying, L.; Engler, M. M.; Cink, R.D.; Lee, C.-S.; Ahmed, F.; Forsyth, C. J. J. Am. Chem. Soc. 2011, 133, 1506 and references therein.
5. (a) Joshi, S.; Bisht, A. S.; Juyal, D. Pharma Innovation 2017, 6, 109-117. (b) Downer-Riley, N. K.; Jackson, Y. A. Curr. Top. Med. Chem. 2016, 16, 3617-3626.
6. www.drugbank.ca; accessed on July 2019.
7. Suárez-Moreno, G.V.; González-Zamora, E.; Méndez, F. Org. Lett. 2011, 13, 6358 and references therein.
8. Dounay, A.B.; Overman, L.E.; Wrobleski, A.D. J. Am. Chem. Soc. 2005, 127, 10186.