Stereoselective synthesis and Cytoselective toxicity of Monoterpene-fused 2-Imino-1,3-Thiazines

Z. Szakonyi, I. Zupkó, Reijo Sillanpää, F. Fülöp

Research output: Article

7 Citations (Scopus)

Abstract

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

Original languageEnglish
Pages (from-to)15918-15937
Number of pages20
JournalMolecules
Volume19
Issue number10
DOIs
Publication statusPublished - okt. 1 2014

Fingerprint

Thiazines
thiazine (trademark)
Monoterpenes
Oxazines
toxicity
Amino Alcohols
Toxicity
Microwaves
alcohols
synthesis
products
Cycloparaffins
Isothiocyanates
microwaves
Thiourea
Microwave irradiation
thioureas
cultured cells
adducts
closures

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Stereoselective synthesis and Cytoselective toxicity of Monoterpene-fused 2-Imino-1,3-Thiazines. / Szakonyi, Z.; Zupkó, I.; Sillanpää, Reijo; Fülöp, F.

In: Molecules, Vol. 19, No. 10, 01.10.2014, p. 15918-15937.

Research output: Article

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