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Molecules 2014, 19(10), 15918-15937; doi:10.3390/molecules191015918

Stereoselective Synthesis and Cytoselective Toxicity of Monoterpene-Fused 2-Imino-1,3-thiazines

1
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary
2
Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
3
Department of Chemistry, University of Jyväskylä, P.O. Box 35, 40351 Jyväskylä, Finland
4
Stereochemistry Research Group of the Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary
*
Authors to whom correspondence should be addressed.
Received: 27 August 2014 / Revised: 22 September 2014 / Accepted: 24 September 2014 / Published: 2 October 2014
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Abstract

Starting from pinane-, apopinane- and carane-based 1,3-amino alcohols obtained from monoterpene-based β-amino acids, a library of monoterpene-fused 2-imino-1,3-thiazines as main products and 2-thioxo-1,3-oxazines as side-products were prepared via two- or three-step syntheses. When thiourea adducts prepared from 1,3-amino alcohols and aryl isothiocyanates were reacted with CDI under mild conditions, O-imidazolylcarbonyl intermediates were isolated which could be transformed to the desired 1,3-thiazines under microwave conditions. 1,3-Thiazines and 2-thioxo-1,3-oxazine side-products could also be prepared in one-step reactions through the application of CDI and microwave irradiation. The ring-closure process was extended to cycloalkane-based γ-hydroxythioureas. The carane- and apopinane-based derivatives exhibited marked antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, A2780, MCF7 and A431). View Full-Text
Keywords: monoterpene; 1,3-amino alcohol; stereoselective; CDI; 1,3-thiazine; antiproliferative monoterpene; 1,3-amino alcohol; stereoselective; CDI; 1,3-thiazine; antiproliferative
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Szakonyi, Z.; Zupkó, I.; Sillanpää, R.; Fülöp, F. Stereoselective Synthesis and Cytoselective Toxicity of Monoterpene-Fused 2-Imino-1,3-thiazines. Molecules 2014, 19, 15918-15937.

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