کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1363888 | 981524 | 2008 | 11 صفحه PDF | دانلود رایگان |

A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a–g″ and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a–c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a–g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner–Wadsworth–Emmons olefination of aldehydes using thus obtained 5-aryl-3-diethoxyphosphoryl-3,4-dihydrofuran-2(5H)-ones 5a–g″ or 5-aryl-3-diethoxyphosphorylpyrrolidin-2-ones 9a–c. Furanones 6 and 11, as well as pyrrolidinones 10 and 12, were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Several of the obtained furanones proved to be very potent against all three cell lines with IC50 values lower than 6 μM. Structure–activity relationships of these compounds, as well as 5-alkyl or 5-arylmethyl-3-methylidenedihydrofuran-2(3H)-ones 13a–e, previously obtained in our laboratory, are discussed.
A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones and 5-aryl-3-methylidenepyrrolidi-2-nones were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates. Target compounds were evaluated for their cytotoxic activity against L-1210, HL-60 and NALM-6 cell lines.Figure optionsDownload as PowerPoint slide
Journal: Bioorganic & Medicinal Chemistry - Volume 16, Issue 9, 1 May 2008, Pages 4872–4882