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An Expeditious Library Synthesis of N-Monoalkylated Aminopiperidines and –pyrrolidines
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2004 Inngår i: European Journal of Organic Chemistry, ISSN 1434-193x, nr 12, s. 2723-2737Artikkel i tidsskrift (Fagfellevurdert) Published
sted, utgiver, år, opplag, sider
2004. nr 12, s. 2723-2737
Identifikatorer
URN: urn:nbn:se:su:diva-25315OAI: oai:DiVA.org:su-25315DiVA, id: diva2:199461
Merknad
Part of urn:nbn:se:su:diva-8038Tilgjengelig fra: 2008-09-11 Laget: 2008-08-25bibliografisk kontrollert
Inngår i avhandling
1. Design and Synthesis of Amine Building Blocks and Protease Inhibitors
Åpne denne publikasjonen i ny fane eller vindu >>Design and Synthesis of Amine Building Blocks and Protease Inhibitors
2008 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The first part of this thesis addresses the design and synthesis of amine building blocks accomplished by applying two different synthetic procedures, both of which were developed using solid-phase chemistry. Chapter 1 presents the first of these methods, entailing a practical solid-phase parallel synthesis route to N-monoalkylated aminopiperidines and aminopyrrolidines achieved by selective reductive alkylation of primary and/or secondary amines. Solid-phase NMR spectroscopy was used to monitor the reactions for which a new pulse sequence was developed. The second method, reported in Chapter 2, involves a novel approach to the synthesis of secondary amines starting from reactive alkyl halides and azides. The convenient solid-phase protocol that was devised made use of the Staudinger reaction in order to accomplish highly efficient alkylations of N-alkyl phosphimines or N-aryl phosphimines with reactive alkyl halides.

The second part of the thesis describes the design and synthesis of three classes of protease inhibitors targeting the cysteine proteases cathepsins S and K, and the serine protease hepatitis C virus (HCV) NS3 protease. Chapter 4 covers the design, solid-phase synthesis, and structure-activity relationships of 4-amidofurane-3-one P1-containing inhibitors of cathepsin S and the effects of P3 sulfonamide groups on the potency and selectivity towards related cathepsin proteases. This work resulted in the discovery of highly potent and selective inhibitors of cathepsin S. Two parallel solid-phase approaches to the synthesis of a series of aminoethylamide inhibitors of cathepsin K are presented in Chapter 5. Finally, Chapter 6 reports peptide-based HCV NS3 protease inhibitors containing a non-electrophilic allylic alcohol moiety as P1 group and also outlines efforts to incorporate this new template into low-molecular-weight drug-like molecules.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2008. s. 77
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-8038 (URN)978-91-7155-690-5 (ISBN)
Disputas
2008-10-03, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2008-09-11 Laget: 2008-08-25 Sist oppdatert: 2010-01-15bibliografisk kontrollert

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