Synthesis of novel Imidazolidinone Peptidomimetics

Synthesis of novel Imidazolidinone Peptidomimetics

Krake, Susann H.; Bergmeier, Stephen C.

Abstract:

Type 1 peptidomimetics are compounds that closely resemble peptides and their activity, but contain variations along the peptide backbone to enhance their stability towards metabolism. Compound 1 contains four such variations, as can be seen by comparison with the corresponding amino acid chain FGGF (Figure 1). The aim of this project is the development of a synthetic route to obtain a new class of peptidomimetics with scaffold A, containing both imidazolidinones and hydroxyethylene isosteres. The key step in the synthesis is the ring opening and rearrangement of fused ring aziridine 2 with an !-aminoamide (Scheme 1).

Type 1 peptidomimetics are compounds that closely resemble peptides and their activity, but contain variations along the peptide backbone to enhance their stability towards metabolism. Compound 1 contains four such variations, as can be seen by comparison with the corresponding amino acid chain FGGF (Figure 1). The aim of this project is the development of a synthetic route to obtain a new class of peptidomimetics with scaffold A, containing both imidazolidinones and hydroxyethylene isosteres. The key step in the synthesis is the ring opening and rearrangement of fused ring aziridine 2 with an !-aminoamide (Scheme 1).

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013820225615

Referências bibliográficas

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• [2] 2852-2859.
• [3] 2 Orac, C. M.; Zhou, S.; Means, J. A.; Boehm, D.; Bergmeier, S.
• [4] C.; Hines, J. V., J. Med. Chem. 2011, 54, 6786-6795.
• [5] 3 Maciagiewicz, I. M.; Fang, F.; Roberts, D. A.; Zhou, S.; Hines, J.
• [6] V.; Bergmeier, S. C., Synthesis-Stuttgart 2012, 44, 551-560.

Como citar:

Krake, Susann H.; Bergmeier, Stephen C.; "Synthesis of novel Imidazolidinone Peptidomimetics", p-193-193. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013820225615