Synthesis of N-Methyl-2-trichloroacetylpyrrole-A Key Building Block in Peptides That Bind DNA: Micro-, Semimicro-, and Macro-Scale Organic Lab Experiments

Autor:	Tyrone V. Arnold, Michael D. Mosher, Erik J. Verner, Nicholas R. Natale, Nicholas Vietri, Daniel Hamlin, Bradford J. Oliver, Robert B. Palmer
Rok vydání:	1996
Předmět:	Chemistry Biological activity General Chemistry Combinatorial chemistry Education Acylation chemistry.chemical_compound Netropsin Molecule Organic chemistry Microscale chemistry DNA Pyrrole Minor groove
Zdroj:	Journal of Chemical Education. 73:1036
ISSN:	1938-1328 0021-9584
Popis:	The search for more efficient anticancer and antiviral agents has included the preparation and testing of a wide variety of molecules that bind DNA. Of these, particular attention has been devoted to the synthesis of analogues of DNA minor-groove binders such as netropsin and distamycin. These compounds have been shown to exhibit biological activity through their strong interactions with the DNA minor groove, and a relationship between their structure and biological activity has emerged (1). The repeating pyrrole unit contained in these compounds can be prepared from N-methylpyrrole via a noncatalyzed Friedel-Crafts acylation. The reaction has been adapted for use in the undergraduate organic chemistry laboratory on three different scales: microscale, semimicroscale, and macroscale.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3554ae5c67fa672f8e9b29ef839daf89 https://doi.org/10.1021/ed073p1036 Zobrazit plný text záznamu