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71. 3,4-Disubstituted oxazolidin-2-ones as constrained ceramide analogs with anticancer activities. Bioorganic & Medicinal Chemistry 19 (2011) 6174–6181

조회 수 52 추천 수 0 2012.01.27 21:49:50
aziridine *.239.207.96

  Alok Singh, Hyun-Joon Ha, Jungchan Park, Jun Hee Kim, Won Koo Lee

 

 Heterocyclic analogs of ceramide as 3-alkanoyl or benzoyl-4-(1-hydroxy-2-enyl)-oxazolidin-2-ones were
designed by binding of primary alcohol and amide in sphinogosine backbone as a carbamate. They were
synthesized by addition of acyl halide to the common ring 4-(1-t-butyldimethylsilyloxyhexadec-2-enyl)-
oxazolidin-2-one which was elaborated from chiral aziridine-2-carboxylate including stereoselective
reduction and ring opening reactions as key steps. Other analogs with different carbon frame at C4
position which is corresponding to the sphingoid backbone were prepared from 3-cyclopentanecarbonyl-
4-(1-t-butyldimethylsilyloxybut-2-enyl)-oxazolidin-2-one and straight and cyclic alkenes by cross
metathesis. All compounds were tested as antileukemic drugs against human leukemia HL-60 cells. Many
of them including propionyl, cyclopentanoyl and p-nitrobenzoyl-4-(1-hydroxyhexadec-2-enyl)-oxazolidin-
2-ones showed better antileukemic activities than natural C2-ceramide with good correlation
between cell death and DNA fragmentation. There is a drastic change of the activities by the carbon chain
lengths at C4 position. Cytotoxicity was induced by caspase activation without significant accumulation
of endogenous ceramide concentration or any perturbation of ceramide metabolism.

 

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