Wanka, Lukas and Cabrele, Chiara and Vanejews, Maksims and Schreiner, Peter R. (2007) gamma-aminoadamantanecarboxylic acids through direct C-H bond amidations. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (9). pp. 1474-1490. ISSN 1434-193X, 1099-0690
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Utilizing bromine-free, direct C-H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or gamma-aminoadamantanecarboxylic acids after hydrolytic cleavage. These rigid analogues of gamma-aminobutyric acid (GABA) were protected at the C- and N-termini and we synthesized a number of peptides incorporating gamma-aminoadamantanecarboxylic acids in solution as well as via solid phase peptide synthesis. These peptides are promising scaffolds for applications in medicinal chemistry as well as in organocatalysis. ((c) Wiley-VCH Verlag GmbH & Co.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ADAMANTANE DERIVATIVES; SUBSTITUTED ADAMANTANES; ALIPHATIC-HYDROCARBONS; TRIFLUOROACETIC-ACID; 1-ADAMANTYL CHLORIDE; BETA-PEPTIDE; AMINO-ACIDS; IN-VITRO; OXIDATION; OLIGOMERS; amino acids; C-H activation; hydrocarbons; peptides; phase-transfer catalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Dr. Chiara Cabrele |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 21 Dec 2020 13:19 |
| Last Modified: | 21 Dec 2020 13:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/33074 |
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