Band 24, Heft 2

The compound ZKY-1 with a D-π-A structure was designed and synthesized in four steps. It undergoes complexation with a tetravalent zirconium ion and the complex can be used for the detection of phosphorylated proteins. The detection limit is estimated to be 100 n m in vitro . The successful detection of phosphorylated proteins in placental tissue samples indicates that this probe holds great potential for clinical diagnosis.

An efficient protocol was developed for the synthesis of 1,2,4-oxadiazinan-5-one derivatives via [3+3] cycloaddition of in situ generated aza-oxyallyl cations with nitrones. This method provides high yields of the heterocyclic products, excellent regioselectivity and broad substrate scope.

1,8-Naphthyridine derivatives are important heterocyclic compounds. A facile and efficient one-pot procedure for the synthesis of 5-(6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5,12-dihydrobenzo[ b ]pyrimido[5,4- g ][1,8]naphthyridine-2,4 (1 H ,3 H )-dione ( 3 ) via a three-component reaction of barbituric acid, 2-chloro-3-formylquinoline and ammonia under basic conditions is described.

A fast (15 min) and efficient cascade reaction of salicylaldehydes and 1,3-dimethylbarbituric acid in the presence of p -TsOH as a catalyst furnishes substituted 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2 H -chromeno[2,3- d ]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1 H ,3 H ,5 H )-triones 1a–h , containing both chromeno[2,3- d ]pyrimidine and hexahydropyrimidine-2,4,6-trione pharmacologically active fragments, in 95–99% yields. This new procedure is characterized by the use of inexpensive reagents and a simple workup.

Novel push-pull fluorescent dyes, 7-(diethylamino)furo[3,2- c ]coumarin and 7-(diethylamino)thieno[3,2- c ]coumarin derivatives, were designed and synthesized using formyl derivatives of furo- and thieno[3,2- c ]coumarins as key intermediates. Electron absorption and emission spectra of the dyes were recorded in different solvents. The longest-wave bands in the electron absorption spectra of the dyes are suggested to be of push-pull nature.

The pH fluorescent probe 7-hydroxy-4-methyl-8-(((2-(1-phenyl-1 H -phenanthro[9,10- d ]imidazol-2-yl)phenyl)imino)methyl)-2 H -chromen-2-one (PICO) contains a donor–π–acceptor (D–π–A) conjugated system. The ‘off−on’ probe PICO has a pKa value of 8.01 and its fluorescence intensity is enhanced with increasing pH.

Reactions of ethyl 4-aryl-2,4-dioxobutanoates 1a–c at ambient temperature with diaminomaleonitrile in glacial acetic acid and with malononitrile in ethanol/H 2 O (1:1) led to the formation of 5-(2-aryl-2-oxoethyl)-6-oxo-1,6-dihydropyrazine-2,3-dicarbontrile 2a–c and ethyl 5-amino-4,6-dicyanobiphenyl-3-carboxylate derivatives 3a–c , respectively.

An efficient and simple one-pot protocol has been developed for synthesis of substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and 6a–g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker’s yeast ( Saccharomyces cerevisiae ). The reaction is enhanced by ultrasonication.

New 1-aryl-4-[(aziridine-1-yl)diarylmethyl]-5-methyl-1 H -1,2,3-triazole derivatives 7a–i were synthesized by a one-pot reaction of diaryl-(1-aryl-5-methyl- 1H -1,2,3-triazol-4-yl)methanols 6a–i derived from 1-aryl-5-methyl-1 H -1,2,3-triazole-4-carboxylic acids 4a–c . Structures of compounds 7a–i were confirmed by analysis of proton nuclear magnetic resonance ( 1 H NMR) and carbon-13 nuclear magnetic resonance ( 13 C NMR), mass spectrometry (MS) and infrared (IR) data. The structure of compound 7f was studied by X-ray diffraction analysis. The anticancer activities of compounds 7a–i against human leukemia HL-60 cells and human hepatoma G2 cells were evaluated. Some of the compounds are highly active.

The title compounds were synthesized and characterized by IR, 1 H NMR, 13 C NMR and HRMS data. Their antimicrobial activities against bacterial strains Escherichia coli and fungal strains Aspergillus niger were evaluated.

Sixteen flavonoid triazolyl glycosides 4–19 were synthesized in good yields via Cu(I)-catalyzed azide-alkyne cycloadditions of terminal alkynes of flavonoids 1–3 with acetylated sugar azides followed by deacetylation with sodium methoxide in anhydrous methanol. The antiproliferative activity of the synthesized compounds against three human cancer cell lines (Hela, HCC1954 and SK-OV-3) in vitro was evaluated. Flavonoids 1 , 2 and flavonoid triazolyl glycosides 7 , 12 , 17 exhibit potent antiproliferative activity against these cancer cell lines.