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Synthesis of a targeted library and thrombin inhibitors using organometallic chemistry
Linköping University, Department of Physics, Chemistry and Biology. Linköping University, The Institute of Technology.
2002 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

The use of organometallic chemistry in the pursuit of novel scaffolds is outline d. A 4-phenyl- 2-carboxy-piperazine targeted combinatorial chemistry library has been synthesized aimed at the early lead discovery phase. This was done using a scaffold that was synthesized by palladium-catalyzed aromatic amination chemistry and subsequently derivatized with 8 electrophiles and I O nucleophiles. Furthermore, ring-closing metathesis chemistry reactions were employed to synthesize the scaffolds cyclopent-2-ene-l, 2-dicarboxylic acid 1-methyl ester and cyclohex-2-ene-1, 2-dicarboxylic acid 1-methyl ester. These were used as proline isosteres in the synthesis of thrombin inhibitors based on the D-Phe-Pro-Arg motif. The scaffolds were derivatized with para-amidino benzylamine and several secondary anilines. A structure-activity relationship study is also described that was based on crystallographic results for one of the inhibitors co-crystallized with thrombin.

Place, publisher, year, edition, pages
Linköping: Linköpings universitet , 2002. , p. 26
Series
Linköping Studies in Science and Technology. Thesis, ISSN 0280-7971 ; 977
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:liu:diva-145980Local ID: LiU-TEK-LIC-2002:50ISBN: 9173734535 (print)OAI: oai:DiVA.org:liu-145980DiVA, id: diva2:1193692
Available from: 2018-03-27 Created: 2018-03-27 Last updated: 2018-10-04Bibliographically approved

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Thorstensson, Fredrik

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