77716-13-3Relevant academic research and scientific papers
Highly efficient synthesis of DNA-binding polyamides using a convergent fragment-based approach
Fallows, Andrew J.,Singh, Ishwar,Dondi, Ruggero,Cullis, Paul M.,Burley, Glenn A.
supporting information, p. 4654 - 4657 (2015/01/08)
Two advances in the synthesis of hairpin pyrrole-imidazole polyamides (PAs) are described. First, the application of a convergent synthetic strategy is shown, involving the Boc-based solid phase synthesis of a C-terminal fragment and the solution phase synthesis of the N-terminal fragment. Second a new hybrid resin is developed that allows for the preparation of hairpin PAs lacking a C-terminal β-alanine tail. Both methods are compatible with a range of coupling reagents and provide a facile, modular route to prepare PA libraries in high yield and crude purity.
Synthesis and evaluation of a netropsin-proximicin-hybrid library for DNA binding and cytotoxicity
Wolter, Falko E.,Molinari, Lise,Socher, Elke R.,Schneider, Kathrin,Nicholson, Graeme,Beil, Winfried,Seitz, Oliver,Suessmuth, Roderich D.
scheme or table, p. 3811 - 3815 (2010/03/25)
The proximicins A-C (1-3) are novel naturally occurring γ-peptides with a hitherto unknown 2,4-disubstituted furan amino acid as a core structure. They show a moderate cytotoxic activity and induce upregulation of cell cycle regulating proteins (p53 and p21) and lead to cell cycle arrest in G0/G1-phase. Hybrid molecules combining structural motifs of the proximicins and of netropsin (4), a structurally related natural product, seem to have similar effects. Herein we describe the synthesis of a netropsin-proximicin-hybrid library and its evaluation regarding cytotoxicity and minor groove binding activity.
Proximicins A, B, and C - Antitumor furan analogues of netropsin from the marine actinomycete Verrucosispora induce upregulation of p53 and the cyclin kinase inhibitor p21
Schneider, Kathrin,Keller, Simone,Wolter, Falko E.,Roeglin, Lars,Beil, Winfried,Seitz, Oliver,Nicholson, Graeme,Bruntner, Christina,Riedlinger, Julia,Fiedler, Hans-Peter,Suessmuth, Roderich D.
supporting information; scheme or table, p. 3258 - 3261 (2009/02/08)
Drugs from the sea: Three new netropsin-type antibiotics (1-3) with a hitherto unknown furan core structure have been isolated from marine actinomycete strains and their structures elucidated by means of mass spectrometry and 2D NMR spectroscopy. The compounds show antitumor activity and, in contrast to netropsin, they induce upregulation of p53 and the cyclin kinase inhibitor p21. (Chemical Equation Presented)
Design, synthesis, DNA binding, and biological activity of a series of DNA minor-groove-binding intercalating drugs
Bailly,Pommery,Houssin,Henichart
, p. 910 - 917 (2007/10/02)
A group of pseudopeptides, molecular combination of the natural antitumor agents distamycin or netropsin and the anilinoacridine chromophore (which is related to the synthetic antileukemic drug amsacrine) has been synthesized. Their DNA binding properties were determined and discussed in terms of their structural differences and in relation to their observed base-dependent binding. Binding data are consistent with a model in which the acridine nucleus occupies an intercalation site and the netropsin or distamycin residue resides in the DNA minor groove. Cytostatic and cytotoxic activities against a murine cell line are reported, as well as significant differences in the inhibition of DNA synthesis.
Novel Efficient Total Synthesis of Antiviral Antibiotic Distamycin A
Grehn, Leif,Ragnarsson, Ulf
, p. 3492 - 3497 (2007/10/02)
In connection with an attempt to design a flexible synthesis of analogues of distamycin A (14) for a structure-activity study, by starting from 4-amino>-1-methylpyrrole-2-carboxylic acid (3) and the corresponding formyl derivative (9), the distamycin A precursor 12 was prepared.The versatility of 12 is demonstrated by direct attachment, after activation, of preformed β-aminopropionamidine dihydrobromide to give 14 in fair yield.We conclude that N- and/or ring-substituted derivatives of 3 and 9 may lead to the corresponding analogues of 12 and thus serve as useful precursors, to which the amino amidine or derivatives thereof can be attached.After hydrogenation of the corresponding nitro compound, 3 and 9 were prepared with (tert-butyloxy)carbonyl fluoride and formic anhydride, respectively.Amide bond formations were accomplished with carbodiimides, occasionally via intermediary active esters (8,13).
