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Synthesis of novel thymine-β-lactam hybrids and evaluation of their anti-tumor activity

Nicola Piens (UGent) , Rob De Vreese (UGent) , Nympha De Neve (UGent) , Kristof Van Hecke (UGent) , Jan Balzarini, Norbert De Kimpe (UGent) and Matthias D'hooghe (UGent)
(2014) SYNTHESIS-STUTTGART. 46(18). p.2436-2444
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Abstract
Trimethylene-tethered thymine-beta-lactam and thyminebis-beta-lactam chimeras were prepared as novel classes of hybrid systems through selective mono-or bis-N-alkylation of thymine with cis-1-(3-bromopropyl)-beta-lactams. In addition, acidic methanolysis of the beta-lactam nucleus in these systems provided an entry into the class of thymine-beta-amino ester hybrids. A selection of the newly synthesized hybrid compounds was assessed for their antiviral activity, cytotoxicity, and cytostatic activity, revealing a significant cytostatic effect of one of the derivatives against murine leukemia and human T-lymphocyte tumor cells.
Keywords
NATURAL-PRODUCTS, RECENT PROGRESS, NUCLEOSIDE CHIMERA, MEDICINAL CHEMISTRY, CONJUGATES SYNTHESIS, SYNTHON METHOD, STEREOSELECTIVE-SYNTHESIS, ASYMMETRIC-SYNTHESIS, BUILDING-BLOCKS, VITRO ANTIMALARIAL EVALUATION, antitumor agents, thymine, acidic methanolysis, beta-lactams, molecular hybridization

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Chicago
Piens, Nicola, Rob De Vreese, Nympha De Neve, Kristof Van Hecke, Jan Balzarini, Norbert De Kimpe, and Matthias D’hooghe. 2014. “Synthesis of Novel Thymine-β-lactam Hybrids and Evaluation of Their Anti-tumor Activity.” Synthesis-stuttgart 46 (18): 2436–2444.
APA
Piens, N., De Vreese, R., De Neve, N., Van Hecke, K., Balzarini, J., De Kimpe, N., & D’hooghe, M. (2014). Synthesis of novel thymine-β-lactam hybrids and evaluation of their anti-tumor activity. SYNTHESIS-STUTTGART, 46(18), 2436–2444.
Vancouver
1.
Piens N, De Vreese R, De Neve N, Van Hecke K, Balzarini J, De Kimpe N, et al. Synthesis of novel thymine-β-lactam hybrids and evaluation of their anti-tumor activity. SYNTHESIS-STUTTGART. 2014;46(18):2436–44.
MLA
Piens, Nicola, Rob De Vreese, Nympha De Neve, et al. “Synthesis of Novel Thymine-β-lactam Hybrids and Evaluation of Their Anti-tumor Activity.” SYNTHESIS-STUTTGART 46.18 (2014): 2436–2444. Print.
@article{4443131,
  abstract     = {Trimethylene-tethered thymine-beta-lactam and thyminebis-beta-lactam chimeras were prepared as novel classes of hybrid systems through selective mono-or bis-N-alkylation of thymine with cis-1-(3-bromopropyl)-beta-lactams. In addition, acidic methanolysis of the beta-lactam nucleus in these systems provided an entry into the class of thymine-beta-amino ester hybrids. A selection of the newly synthesized hybrid compounds was assessed for their antiviral activity, cytotoxicity, and cytostatic activity, revealing a significant cytostatic effect of one of the derivatives against murine leukemia and human T-lymphocyte tumor cells.},
  author       = {Piens, Nicola and De Vreese, Rob and De Neve, Nympha and Van Hecke, Kristof and Balzarini, Jan and De Kimpe, Norbert and D'hooghe, Matthias},
  issn         = {0039-7881},
  journal      = {SYNTHESIS-STUTTGART},
  keywords     = {NATURAL-PRODUCTS,RECENT PROGRESS,NUCLEOSIDE CHIMERA,MEDICINAL CHEMISTRY,CONJUGATES SYNTHESIS,SYNTHON METHOD,STEREOSELECTIVE-SYNTHESIS,ASYMMETRIC-SYNTHESIS,BUILDING-BLOCKS,VITRO ANTIMALARIAL EVALUATION,antitumor agents,thymine,acidic methanolysis,beta-lactams,molecular hybridization},
  language     = {eng},
  number       = {18},
  pages        = {2436--2444},
  title        = {Synthesis of novel thymine-β-lactam hybrids and evaluation of their anti-tumor activity},
  url          = {http://dx.doi.org/10.1055/s-0033-1338647},
  volume       = {46},
  year         = {2014},
}

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