- Synthesis of enantiopure dehydropiperidinones from α-amino acids and alkynes via azetidin-3-ones
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Chiral dehydropiperidinones were synthesized in enantiopure form from α-amino acids and alkynes via azetidin-3-ones.
- Ishida, Naoki,Yuhki, Tatsuya,Murakami, Masahiro
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supporting information; experimental part
p. 3898 - 3901
(2012/09/22)
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- Synthesis of cyclo-β-tripeptides and their biological in vitro evaluation as antiproliferatives against the growth of human cancer cell lines
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A number of cyclo-β-tripeptides and their linear precursors were subjected to primary biological evaluation for cancer-cell growth inhibition (one-dose, three-cell essay), and the five most active ones were then tested in the anti-tumor screen of the National Cancer Institute (Bethesda, USA) with 60 human cancer cell lines. Growth inhibition values GI50 in the one-digit micromolar, and in one case in the nanomolar range were obtained. The effects show selectivities for certain types of cancer cells and for certain cell lines within these types; the screen includes leukemia, non-small-cell lung, colon, and central-nervous-system (CNS) cancer, melanoma, ovarian, renal, prostate, and breast cancer cell lines. The synthesis and full characterization of two new cyclo-β-peptides, (β3-HSer(OBn))3 (11) and (β3-HMet)3 (12) are described. Other cyclo-β-peptides included in this investigation are (βAsp(Bn))3 (13), (β-HGlu(Bn))3 (14), and (β-HAla)3 (16), compounds which had been previously prepared by us. Strongest activities were measured with the cyclo-β-peptides bearing benzyl-ester or benzyl-ether groups in the side chains. The cytotoxic activity of the compounds included in this investigation is much lower (LC50 > 100 μM) than their antiproliferative activity (GI50).
- Gademann, Karl,Seebach, Dieter
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p. 2924 - 2937
(2007/10/03)
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- The synthesis of di(hydroxyalkyl) substituted bicyclic guanidines
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The synthesis of the enantiomerically pure bicyclic guanidines 3a and 3b is described.The convergent strategy is based on methodology developed by Schmidtchen.The therefore required amine components 6 and 9 obtained from methionine and L-glutamic acid, respectively.
- Madder, A.,Muenster, I.,Rolle, U.,Clercq, P. J. De
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p. 613 - 622
(2007/10/03)
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- Synthesis of a Chiral Di(hydroxyalkyl) Substituted Bicyclic Guanidine
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Schmidtchen's methodology is used successfully for the synthesis of the chiral disubstituted bicyclic guanidinium salt 2.The two therefore required primary amine compounds 6 and 9 are obtained from L-methionine and L-glutamic acid, respectively.
- Muenster, Ingo,Rolle, Ulrike,Madder, Annemieke,Clerq, Pierre J. De
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p. 2673 - 2674
(2007/10/03)
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