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 firstname.lastname@example.org.
- 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.
- König, G.M.; Kehraus, S.; Seibert, S.F.; Abdel-Lateff, A.; Müller, D. ChemBioChem 2006, 7, 229.
- Hofle, G.H.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem. Int. Ed. 1996, 35, 1567.
- (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.
- 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.
- Dondoni, A.; Marra, A. Chem. Rev. 2004, 104, 2557.
- Velazquez, F.; Olivo, H.F. Curr. Org. Chem. 2002, 6, 303.
- (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.
- (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.