Search

Novel thiopyrano[2,3-d]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5H)furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5H)furanone was studied by DFT at the M06-2X/6-31+G(d,p) level. The stereo- and regioselectivities of cycloaddition were confirmed by NMR spectra and single-crystal X-ray diffraction analyses.

The screening of the in vitro anticancer activity of the synthesized compounds shows that compounds (IVa), (VIIIb), (VIIId) are the most active compounds against different cell lines.

Poly( N -methacryloyl- l -leucine) (PNML) coatings were successfully fabricated via polymerization from peroxide initiator grafted to premodified glass substrate. Chemical composition and thickness of PNML coatings were determined using time of flight-secondary ion mass spectrometry (TOF- SIMS) and ellipsometry, respectively. PNML coatings exhibit thermal response of the wettability, between 4 and 28 °C, which indicates a transition between hydrated loose coils and hydrophobic collapsed chains. Morphology of the PNML coating was observed with the AFM, transforming with increasing temperature from initially relatively smooth surface to rough and more structured surface. Protein adsorption observed by fluorescence microscopy for model proteins (bovine serum albumin and lentil lectin labeled with fluorescein isothiocyanate) at transition from 5 to 25 °C, showed high affinity of PNML coating to proteins at all investigated temperatures and pH. Thus, PNML coating have significant potential for medical and biotechnological applications as protein capture agents or functional replacements of antibodies (“plastic antibodies”). The high proliferation growth of the human embryonic kidney cell (HEK 293) onto PNML coating was demonstrated, indicating its excellent cytocompatibility.

A new approach to the synthesis of new heterocyclic compounds with triazine and 4-thiazolidone fragments in one molecule is developed. The synthesis methods comprise [2+3]-cyclocondensation reactions essential in the preparative synthesis of 4-thiazolidone derivatives. The reactions of S,N-nucleophiles with C2-cyclization agents for the synthesis of a number of biologically active 2-triazin-4-thiazolidones were investigated. The interaction of thiosemicarbazone of sym-triazine with derivatives of α-halogencarboxylic acids and maleic anhydride resulted in correspondent (2-[2-(4,6-dichloro-1,3,5-triazin-2-yl)hydrazino]-5-(3,4,5- R-p-phenyl-methyliden)-1,3-thiazol-4-ones obtained in the one-step synthesis. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:392–396, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20631