| Differentially-protected steroidal triamines; scaffolds with potential for medicinal, supramolecular, and combinatorial chemistry. | |
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MedLine Citation:
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PMID: 15534710 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Cholic acid 2a has been converted into two new orthogonally-protected triamino scaffolds, 13 and 14. The synthesis proceeds via the bis-Boc-NH-substituted azide 10, for which an improved preparation is described. After removal of the Boc groups, the two axial amines are differentiated through a novel monoprotection employing 1-(2-nitrobenzenesulfonyloxy)-benzotriazole 29. Regioselectivity of > or 50 : 1 is achieved, presumably reflecting an exceptional sensitivity to steric hindrance. Protection of the remaining amino group as Boc or Alloc gives the scaffolds in approximately 40% overall yield from cholic acid. Scaffold 13 has been sequentially deprotected and derivatised with N-carbamoyl amino acids, to give a model for tripodal peptide libraries. |
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Authors:
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Vicente del Amo; Laura Siracusa; Theodoros Markidis; Beatriz Baragaña; Khadga M Bhattarai; Marta Galobardes; Gregorio Naredo; M Nieves Pérez-Payán; Anthony P Davis |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2004-10-15 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 2 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2004 Nov |
Date Detail:
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Created Date: 2004-11-09 Completed Date: 2006-06-22 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3320-8 Citation Subset: IM |
Affiliation:
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School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry Azides / chemistry Chemistry, Organic / methods* Cholic Acid / chemistry* Combinatorial Chemistry Techniques Molecular Structure Polyamines / chemical synthesis*, chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Azides; 0/Polyamines; 81-25-4/Cholic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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