We Prepared a Set of Functionalized 1,3-Thiazoles to Power Up Your Research

The structural unit of substituted 1,3-thiazole is ubiquitous in natural products and synthetic materials.¹

Thiazole-containing natural products isolated from cyanobacteria of different marine organisms include small linear peptides (e.g., nordysidenin 1 in Fig. 1), linear oligopeptides (so-called Apramidas), cyclic peptides (e.g., tenuecyclamide A 2 in Fig. 1), and alkaloids.² Moreover, a few macrocycles and cyclic lactones bearing the thiazole ring were found in some soil bacteria extracts.³

1,3-Thiazole is a privileged scaffold in drug discovery. Many thiazole-based compounds have anti-tumor, antifungal, and enzyme-inhibiting activities;⁴ some of them are presently approved drugs.⁵ 1,3-Thiazoles are also indispensable in organic synthesis as place-holding groups for the formyl functionality⁶ and chiral auxiliaries⁷ in asymmetric reactions.

1,3-Thiazole-derived fluorescent dyes, such as Thiazole Orange 3, have found important applications in cytometry as “light-up” probes for DNA. Technology benefits from thiazole-containing semiconducting conjugated polymers⁸ and catalysts, such as compound 4⁹ in Fig. 1. 

Figure 1. The occurrence of the thiazole ring in natural products and synthetic molecules

Life Chemicals offers diversely functionalized 1,3-thiazole building blocks. Some selected structures featuring a 1,3-thiazole ring are listed below. The full database of the functionalized 1,3-thiazoles is available upon request at orders@lifechemicals.com.

References:

1. Chen B.; Heal, W. 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. 635.
2. König, G.M.; Kehraus, S.; Seibert, S.F.; Abdel-Lateff, A.; Müller, D. ChemBioChem 2006, 7, 229.
3. Hofle, G.H.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem. Int. Ed. 1996, 35, 1567.
4. (a) Kumar, S.; Patil, M. T.; Kataria, R.; Salunke, D. B. Eds. Gupta, G. K.; Vinod, K. Chem. Drug Design 2016, 243-281. (b) Thorat, B. R.; Joshi, V.; Thorat, V. B. Heterocycl. Lett. 2016, 6, 389-409.
5. According to www.drugbank.ca as of September 2019 there are 28 thiazole-containing marketed drugs. These drugs include natural products, natural-product-based architectures, and purely synthetic compounds.
6. Dondoni, A.; Marra, A. Chem. Rev. 2004, 104, 2557.
7. Velazquez, F.; Olivo, H.F. Curr. Org. Chem. 2002, 6, 303.
8. (a) Subramaniyan, S.; Kim, F.S.; Ren, G.; Li, H.; Jenekhe, S.A. Macromolecules 2012, 45, 9029. (b) Hussain, S.; De, S.; Iyer, P.K. ACS Appl. Mater. Interfaces 2013, 5, 2234.
9. (a) Luo, Q.-L.; Tan, J.-P.; Li, Z.-F.; Nan, W.-H.; Xiao, D.-R. J. Org. Chem. 2012, 77, 8332. (b) Frija, L. M. T.; Pombeiro, A. J. L.; Kopylovich, M. N. Coord. Chem. Rev. 2016, 308, 32-55.