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

作者：Szakonyi Zsolt^*; Zupko Istvan; Sillanpaa Reijo; Fueloep Ferenc

来源：Molecules, 2014, 19(10): 15918-15937.

DOI：10.3390/molecules191015918

• monoterpene
• 1,3-amino alcohol
• stereoselective
• CDI
• 1,3-thiazine
• antiproliferative

Starting from pinane-, apopinane- and carane-based 1,3-amino alcohols obtained from monoterpene-based beta-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 gamma-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).

• 出版日期2014-10