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Synthesis of 2-(2-Aminopyrimidine)-2,2-difluoroethanols as Potential Bioisosters of Salicylidene Acylhydrazides
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2010 (English)In: Molecules, ISSN 1420-3049, Vol. 15, no 6, 4207-12 p.Article in journal (Refereed) Published
Abstract [en]

Salicylidene acylhydrazides are inhibitors of type III secretion in several Gramnegative pathogens. To further develop the salicylidene acylhydrazides, scaffold hopping was applied to replace the core fragment of the compounds. The novel 2-(2-aminopyrimidine)-2,2-difluoroethanol scaffold was identified as a possible analog to thesalicylidene acylhydrazide core structure. The synthesis of a library of 2-(2-aminopyrimidine)-2,2-difluoro-ethanols is described in this paper.

Place, publisher, year, edition, pages
2010. Vol. 15, no 6, 4207-12 p.
Keyword [en]
scaffold hopping, Reformatsky reaction, salicylidene acylhydrazide, type III secretion
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-34860DOI: 10.3390/molecules15064423ISI: 000279207300043OAI: oai:DiVA.org:umu-34860DiVA: diva2:326141
Available from: 2010-06-22 Created: 2010-06-22 Last updated: 2014-03-10Bibliographically approved
In thesis
1. Statistical molecular design, QSAR modeling, and scaffold hopping – Development of type III secretion inhibitors in Gram negative bacteria
Open this publication in new window or tab >>Statistical molecular design, QSAR modeling, and scaffold hopping – Development of type III secretion inhibitors in Gram negative bacteria
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Type III secretion is a virulence system utilized by several clinically important Gram-negative pathogens. Computational methods have been used to develop two classes of type III secretion inhibitors, the salicylidene acylhydrazides and the acetylated salicylanilides. For these classes of compounds, quantitative structure-activity relationship models have been constructed with data from focused libraries obtained by statistical molecular design. The models have been validated and shown to provide useful predictions of untested compounds belonging to these classes. Scaffold hopping of the salicylidene acylhydrazides have resulted in a number of synthetic targets that might mimic the scaffold of the compounds. The synthesis of two libraries of analogs to two of these scaffolds and the biological evaluation of them is presented.

Place, publisher, year, edition, pages
Umeå: VMC-KBC, 2010. 65 p.
Keyword
Statistical molecular design, QSAR, synthesis, type III secretion, virulence, scaffold hopping
National Category
Organic Chemistry
Research subject
läkemedelskemi
Identifiers
urn:nbn:se:umu:diva-32506 (URN)978-91-7264-976-7 (ISBN)
Public defence
2010-04-16, KB3B1, Umeå Universitet, kemiska Institutionen, Linaeus v., KBC, 10:00 (Swedish)
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Available from: 2010-03-18 Created: 2010-03-15 Last updated: 2014-03-10Bibliographically approved

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Öberg, Christopher TElofsson, Mikael

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