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New proline mimetics: Synthesis of thrombin inhibitors incorporating cyclopentane- and cyclopentenedicarboxylic acid templates in the P2 position. Binding conformation investigated by X-ray crystallography
AstraZeneca, Dept Med Chem, S-43183 Molndal, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden.
AstraZeneca, Dept Med Chem, S-43183 Molndal, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
AstraZeneca, Dept Med Chem, S-43183 Molndal, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden.
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2000 (English)In: Journal of Medicinal Chemistry, ISSN 0022-2623, Vol. 43, no 9, 1705-1713 p.Article in journal (Refereed) Published
Abstract [en]

With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).

Place, publisher, year, edition, pages
2000. Vol. 43, no 9, 1705-1713 p.
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Engineering and Technology
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URN: urn:nbn:se:liu:diva-49760OAI: oai:DiVA.org:liu-49760DiVA: diva2:270656
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2011-01-14

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Kvarnström, Ingemar

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