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Multicomponent Reac...
Multicomponent Reactions in 11C/12C Chemistry : – Targeting the Angiotensin II Subtype 2 Receptor
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- Stevens, Marc, 1984- (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Odell, Luke, Docent (thesis advisor)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Larhed, Mats, Professor (thesis advisor)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Antoni, Gunnar, Adjunct Professor (thesis advisor)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Estrada, Sergio, Forskare (thesis advisor)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Åberg, Ola, Forskare (thesis advisor)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Vasdev, Neil, Associate Professor (opponent)
- Harvard Medical School
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(creator_code:org_t)
- ISBN 9789155496364
- Uppsala : Acta Universitatis Upsaliensis, 2016
- English 93 s.
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Series: Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, 1651-6192 ; 219
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Abstract
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- Section 1 of this thesis contains an introduction to method development in organic synthesis, multicomponent reactions, sulfonyl azides, tracer development in 11C chemistry and the biological target.Section 2 describes the use of sulfonyl azides in carbonylative chemistry. Paper I covers development of a diazotransfer protocol. In total, 30 arylsulfonyl azides were synthesised from primary sulfonamides (20–90% yield). 15N mechanistic studies were carried out and in Paper II, the products were converted into sulfonamides, sulfonylureas and sulfonyl carbamates (19–90% yield). For ureas and carbamates, a two-chamber protocol was employed to release CO from Mo(CO)6. 15N mechanistic studies showed that the sulfonamides were formed by direct displacement of azide.Section 3 covers imaging and biological studies of the angiotensin II receptor subtype 2 (AT2R). In Paper III, 12 11C-sulfonyl carbamates were prepared in isolated radiochemical yields of 3–51% via Rh(I)-mediated carbonylation. The first non-peptide AT2R agonist, C21, was labelled (isolated RCY 24±10%, SA 34–51 GBq/µmol). C21 was tested in a prostate cancer assay, followed by biodistribution and small-animal PET studies. In Paper IV, a 11C-labelled AT2R ligand prepared via Pd(0)-mediated aminocarbonylation was used for autoradiography, biodistribution and small-animal PET studies. Section 4 describes the development of a multicomponent method for the synthesis of 3,4-dihydroquinazolinones (Paper V). 31 3,4-dihydroquinazolinones were synthesized via a cyclic iminium ion.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- carbonylation
- positron emission tomography
- multicomponent reactions
- AT2R
- 3
- 4-dihydroquinazolinone
- sulfonyl azides
- Farmaceutisk vetenskap
- Pharmaceutical Science
Publication and Content Type
- vet (subject category)
- dok (subject category)
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Stevens, Marc, 1 ...
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Odell, Luke, Doc ...
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Larhed, Mats, Pr ...
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Antoni, Gunnar, ...
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Estrada, Sergio, ...
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Åberg, Ola, Fors ...
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Vasdev, Neil, As ...
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NATURAL SCIENCES
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Uppsala University