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Review
. 2012 Jun 25;17(7):7612-28.
doi: 10.3390/molecules17077612.

Thiadiazines, N,N-heterocycles of biological relevance

Hortensia Rodríguez  1 , Margarita Suárez, Fernando Albericio
Affiliations
Review

Thiadiazines, N,N-heterocycles of biological relevance

Hortensia Rodríguez et al. Molecules. .

Abstract

The 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold has found many applications in recent years. This review is aimed at highlighting the most important aspects of these compounds: synthesis, spectroscopic characterization and biological activities. How the chemical nature of N-substituents influences the overall activity and cytotoxicity profile will also be discussed.

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Figures

Figure 1
Figure 1
The 3,5-dimethyltetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold.
Figure 2
Figure 2
THTT structures.
Scheme 1
Scheme 1
Synthesis of mono-THTT scaffold.
Scheme 2
Scheme 2
Solid phase synthesis of mono-THTT scaffolds.
Scheme 3
Scheme 3
Synthesis of bis-THTTs scaffold.
Scheme 4
Scheme 4
Synthesis of spermidyl linked bis-THTT scaffold.
Scheme 5
Scheme 5
Proposed mechanisms for the THTT ring formation.
Figure 3
Figure 3
THTT derivatives characterized by NMR studies.
Figure 4
Figure 4
Mono-THTT derivatives tested against T. cruzi and T. vaginalis.
Figure 5
Figure 5
THTT derivatives with anti-amastigote activity.
Figure 6
Figure 6
Bis-THTT derivatives with antiprotozoal activity.
Figure 7
Figure 7
The promising THTT derivatives 21 and 22 for a future anticancer study.
Figure 8
Figure 8
THTT derivatives with antuberculosis activity.
Figure 9
Figure 9
THTT derivatives with antibacterial and antifungal activity.
Figure 10
Figure 10
THTT derivatives of β-alanine with antifungal activity (against C. albicans and F. oxysporum).
Figure 11
Figure 11
THTT derivative with antimicrobial activity against S. aureus, B. subtilis, E. coli and P. aeruginosa.
Figure 12
Figure 12
3-Substituted-5-(2-hydroxyethyl)-THTT derivatives.
Figure 13
Figure 13
THTT derivative of glycine with antifungal activity.
Figure 14
Figure 14
3,3'-ethylenebis(5-alkyl)-THTTs (37) tested as antifungal compounds.
Figure 15
Figure 15
2,3-bis(5-Alkyl-2-thiono-1,3,5-thiadiazin-3-yl)propionic acids 40 and their corresponding N,N-dimethylpropionamides 41 tested as antibacterial and antifungal compounds.
Figure 16
Figure 16
3-Phenyl-5-(substituted)-THTT derivatives 42 and 43, and others THTT derivatives (44 and 45) tested as antibacterial and antifungal compounds.
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