Thiazole alkaloid

Multicomponent reactions in alkaloid-based drug discovery 12KGS38. Muscarine, imidazole, oxazole, and thiazole alkaloids 13NPR869. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids 12CRV3193. 

Jin Z (2009) Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep 26 382-445... 

Lewis, J. R. 2001. Amaryllidaceae, muscarine, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids. Nature Product Reports, 18 95-128. 

Thiazole-containing pyridoacridines are a group of fused ring alkaloids having a pyrido[4,3,2-w, ]thiazolo[3,2-6]acridinium skeleton related to shermilamines, varamines and diplamine, which were discussed in the sulfide section [37]. The pyridoacridines have a characteristic UV absorption pattern [A.max(MeOH) 245, 307, and 361 nm], which is highly sensitive to the pH of the medium. 

Pyridoacridine alkaloids have been isolated from sponges ascidians, anemones, and a prosobranch. Two thiazole-containing compounds were obtained, namely kuanoniamine E, 429, and kuanoniamine E, 430 <2002JNP1198>. 

Thiazine containing alkaloids are relatively rare in Nature, but they range in structural complexity from simple monocyclic derivatives such as chondrine and benzothiazines such as the aplidinones, to more complex tri- and polycyclic compounds exemplified by ansafhiazin and the shermilamines. On the other hand, the simplest N,S-heterocycle - the 5-membered thiazole - is relatively common in Nature, and, for example, plays a vital role in the function of thiamine (vitamin Bi). Thiazole rings also occur in important biologically active natural products such as the epothilones (Figure 1). 

The structure of the un-named alkaloid (19) obtained from a Thermoac-tinomyces strain has been confirmed by a simple synthesis from tryptamine and the thiazole amino-acid (20), prepared from (+)-(5)-alanine (Scheme 2). ... 

---