768
O. Mesenzani et al. / Bioorg. Med. Chem. Lett. 21 (2011) 764–768
Figure 7. FACS analysis of the selected compounds. Cells were stained propidium iodide to investigate DNA content. Data are representative of at least 6 cytofluorimeter
analysis in two experimental days.
10. The ynone intermediate 14, was already synthesized by reacting the
Acknowledgments
corresponding acetylene derivative with p-anisaldehyde, followed by alcohol
oxidation, but it has never been reported its biological evaluation see: Kerr, D.
Financial support from Università degli Studi del Piemonte
Orientale and M.I.U.R. PRIN 2008 Italy, is gratefully acknowledged.
J.; Hamel, E.; Jung, M. K.; Flynn, B. L. Bioorg. Med. Chem. 2007, 15, 3290.
11. Giustiniano, M.; Pirali, T.; Massarotti, A.; Biletta, B.; Novellino, E.; Campiglia, P.;
Sorba, G.; Tron, G. C. Synthesis 2010, 23, 4107.
12. Synthetic procedure for compound 18d: equimolar amounts of 5-isocyano-2-
References and notes
methoxyphenol,
3,4,5-trimethoxybenzaldehyde,
benzylamine
and
trimethylsilylazide were dissolved in dry methanol (2 M) under a nitrogen
atmosphere. The resulting solution was stirred at room temperature for three
days. The solid formed was filtered off and washed with cold methanol to give
16d as a yellow solid (75%). The obtained tetrazole intermediate was then
stirred in methanol under a hydrogen atmosphere in the presence of Pd/C 10%
heating at 60 °C for 24 h. The crude reaction was filtered through a Celite pad
and evaporated to give the free amine 17d as a yellow oil (65%) which was
enough pure for the following step. The amine was dissolved in CH2Cl2/DMF
3:1 and 4-formyl-1-methylpyridinium benzenesulfonate (1.2 equiv) was
added. The reaction mixture was stirred at room temperature for 8 h, then
treated with triethylamine (1.0 equiv) and stirred for 15–20 min. The reaction
was finally quenched with a cold saturated aqueous solution of oxalic acid and
stirred overnight. The reaction was then diluted with water and CH2Cl2. After
extraction with CH2Cl2 (3Â) the combined organic phases were washed with
brine (1Â), dried over sodium sulfate, filtered, and evaporated under reduced
pressure. The carbonyl compound was purified by column chromatography
using PE/EtOAc as eluent to give 18d as a yellow solid (46%): IR (KBr) 1643,
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;
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