874908-41-5Relevant academic research and scientific papers
Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides
Abu-Zaied,El-Telbani,Elgemeie,Nawwar
experimental part, p. 229 - 235 (2011/02/27)
A facile, convenient and high yielding synthesis of novel thioglycosides incorporating 1,3,4-oxadiazole, triazole and or triazine moieties from readily available starting materials has been described. The key step of this protocol is the formation of 3-isobutyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3) via condensation between methyl iso-butyl ketone and phenylhydrazine followed by application of Vilsmeier-Haack reaction. 3 was converted either to 1,3,4-oxadiazole derivative or condensed with O-aminothiols to give the bases 8, 19 and 20 in good yields, respectively. The aglycons 8, 19, and 20 were coupled with different activated halosugars in the presence of basic medium. Pharmacological evaluation of compounds 8, 14, 16 and 22 in vitro against 2-cell lines MCF-7 (breast) and HEPG2 (liver) revealed them to possess high anti-tumor activities with IC50 values ranging from 2.67-20.25 (μg/mL) for breast cell line (MCF-7) and 4.62-43.6 (μg/mL) for liver cell line (HEPG2). None of the tested compounds exhibited any toxicity in doses up to 500 mg kg-1 of the animal body weight.
Vilsmeier formylation of hydrazones and semicarbazones derived from alkyl, benzyl, and cycloalkyl methyl ketones
Lebedev,Lebedeva,Sheludyakov,Kovaleva,Ustinova,Kozhevnikov
, p. 412 - 416 (2007/10/03)
Formylation of ten accessible phenylhydrazones and semicarbazones derived from alkyl, benzyl, and cycloalkyl methyl ketones with the complex of POCl 3 with dimethylformamide was studied. Depending on the electronic and steric structure of the substrates, the reaction yields 1-phenyl- or 1-unsubstituted 3,4-dialkyl-, 3-alkyl-4-aryl-, or 3-alkyl-4-formylpyrazoles. These compounds can be readily oxidized into the corresponding carboxylic acids. 2005 Pleiades Publishing, Inc.
