Synthesis of pyrrole-imidazole polyamide oligomers based on a copper-catalyzed cross-coupling strategy

[Display omitted] Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2017-05, Vol.27 (10), p.2197-2200
Main Authors: Shiga, Naoki, Takayanagi, Shihori, Muramoto, Risa, Murakami, Tasuku, Qin, Rui, Suzuki, Yuta, Shinohara, Ken-ichi, Kaneda, Atsushi, Nemoto, Tetsuhiro
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Binding Sites
Catalysis
Copper
Copper - chemistry
Cross-coupling
DNA - chemistry
DNA - metabolism
Imidazoles - chemistry
Nylons - chemistry
Polyamides
Pyrroles - chemistry
Synthetic methods
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Summary:[Display omitted] Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling strategy. All four patterns of dimer fragments could be synthesized using a Cu-catalyzed Ullmann-type cross-coupling with easily prepared monomer units. Moreover, we demonstrated that pyrrole dimer, trimer, and tetramer building blocks for Py-Im polyamide synthesis were accessible by combining site selective iodination of the pyrrole/pyrrole coupling adduct.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.03.052