KW - C-nucleosides: thiazofurin analogues

This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value.

Various laboratory methods exist for the of thiazoles.

T1 - Synthesis of new 1,4-dihydropyridine derivatives containing thiazolyl substituents

The reactivity of a thiazole can be summarized as follows:


Rambaldi, “Novel thiazole derivatives: A patent review (2008 - 2012.

De Aquino TM, Liesen AP, da Silva REA, Lima VT, Carvalho CS, de Faria AR, et al. Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids. Bioorg Med Chem 2008;16:446-56.

T1 - Thiazole C-nucleosides. III. Synthesis of pyranose analogues of tiazofurin

(3 H )-thiazoles in excellent yields

Starting from -alanine, bacillamide C (3), was obtained in 22% overall yield []. The key intermediate, thiazole 35, , was synthesized using Hantzsch reaction.

Etude du mécanisme de la reaction de hantzsch des thiazoles

When a base is added in solution, a drastic change of absorption and of fluorescence is observed. The lactone ring-opening process leads to deprotonated 4-hydroxythiazoles, which, due to their electronically altered π-systems, display fluorescence in the orange to red region of the visible spectrum. Derivatives ,, and, which form pyridinium ions and compounds , which contain an additional aza-nitrogen in the neighboring pyridine ring, show a strong green fluorescence upon the addition of acids­. A geometry change is discussed as a reason for this unusual shift.

Define thiazole | Dictionary and Thesaurus

During 2009, six reports related to the synthesis of largazole and/or analogs were published [–]. A significant increase in potency with a pyridine substitution of the thiazole was reported. In addition, it was demonstrated that the methyl substituent of the thiazoline ring is nonessential for the dramatic potency of the natural product. In contrast, substitution of the thiazoline by thiazol, diminishes the activity [].

Thiazole - Infogalactic: the planetary knowledge core

Recently, the first total synthesis and a revised configurational assignment of bisebromoamide were reported []. The authors synthesized the originally proposed structure (26), , but, neither NMR spectra nor optical rotation for the obtained compound were identical with those of the natural product. The authors elected to synthesize the epimer with R-configuration of the stereogenic center at the thiazoline ring of the proposed structure (41), , from different fragments as is shown in the retrosynthetic analysis. The spectral data and optical rotation for 41 were identical to those of the natural product leading to a revision of the reported stereochemistry of bisebromoamide.

a Hantzsch reaction to generate the thiazole, ..

The cytotoxic thiazoline, apratoxin A (37), , was synthesized in 18 steps and 18% overall yield. In addition, an oxazoline analogue (38) and 34-epiapratoxin A (39) were obtained []. The synthetic strategy to obtain apratoxin A involves the preparation of fragment 40 through a stereoselective route based in three asymmetric reactions. Thiazoline formation was successfully accomplished from a Cys amide using Ph3PO/Tf2O and macrolactamization was performed between N-methylisoleucine and proline residues using HATU.

Significance of Thiazole-based Heterocycles for Bioactive ..

A thiazole Ugi multicomponent reaction and an aminolisis reaction were used to obtain racemic Bacillamide C, []. Additionally, several analogs of this natural product and a fluoro derivative of neobacillamide (4), , were synthesized.