77716-16-6Relevant articles and documents
Synthesis of distamycin a polyamides targeting G-quadruplex DNA
Moore, Michael J. B.,Cuenca, Francisco,Searcey, Mark,Neidle, Stephen
, p. 3479 - 3488 (2008/09/17)
A number of amide-linked oligopyrroles based on distamycin molecules have been synthesized by solid-state methods, and their interactions with a human intramolecular G-quadruplex have been measured by a melting procedure. Several of these molecules show an enhanced ratio of quadruplex vs. duplex DNA binding compared to distamycin itself, including one with a 2,5-disubstituted pyrrole group. Quadruplex affinity increases with the number of pyrrole groups, and it is suggested that this is consistent with a mixed groove/G-quartet stacking binding mode. The Royal Society of Chemistry 2006.
Method for the synthesis of pyrrole and imidazole carboxamides on a solid support
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, (2008/06/13)
The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.
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).
