Synthesis and NMR characterization of selectively 15N-labelled trans- and cis-butenediamido-linked bis-netropsins
✍ Scribed by Bertrand Plouvler; Malvinder P. Singh; J. William Lown
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- French
- Weight
- 766 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
The synthesis of specifically 15N labelled trans-and cis-isomers of bis-netropsins derived from P-butene-1,4-dicarboxylate as the central linker, namely the (9and (Z)-forms of N-[2-
yl]-2-butenediamide (18 8 28) are described. A highly convergent synthetic route was adopted for the preparation of the trenederivative starting from N-methyl-4-nitro-2-trichloroacetylpyrrole and fumaroyl chloride. The most efficient methods of coupling aminopyrrole intermediates with activated carboxylic acid derivatives were utilized and the 15N-labelled moieties were incorporated in the later stages of the synthesis. The preparation of the cisderivative, starting with maleic anhydride, required a modification of the above strategy due to the nature of products formed upon initial coupling with aminopyrrole derivatives. lHand lCN-NMR were used to fully characterize the final products. The 'H NMR experiment allowed the assignment of an intramolecular hydrogen bond for the cis bis-netropsin 28.