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Chow, Shiao
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Publications (4 of 4) Show all publications
Chow, S. Y., Odell, L. R. & Eriksson, J. (2016). Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation. European Journal of Organic Chemistry (36), 5980-5989
Open this publication in new window or tab >>Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 36, p. 5980-5989Article in journal (Refereed) Published
Abstract [en]

A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

Keywords
Radical reactions, Carbon isotopes, Carbon monoxide, Xenon, Radical initiator, Reductive dehalogenation, Radiochemistry, Carbonylation
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-316439 (URN)10.1002/ejoc.201601106 (DOI)000392534600010 ()
Funder
Carl Tryggers foundation , CTS13:333/14:356
Available from: 2017-03-01 Created: 2017-03-01 Last updated: 2018-01-13Bibliographically approved
Chow, S., Stevens, M. & Odell, L. (2016). Sulfonyl Azides as Precursors in Ligand-free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides. Journal of Organic Chemistry, 81(7), 2681-2691
Open this publication in new window or tab >>Sulfonyl Azides as Precursors in Ligand-free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
2016 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 81, no 7, p. 2681-2691Article in journal (Refereed) Published
Abstract [en]

An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)(6), were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.

National Category
Natural Sciences
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-281023 (URN)10.1021/acs.joc.5b02755 (DOI)000373520200001 ()26967791 (PubMedID)
Funder
Knut and Alice Wallenberg FoundationCarl Tryggers foundation
Available from: 2016-03-16 Created: 2016-03-16 Last updated: 2017-11-30Bibliographically approved
Stevens, M., Chow, C., Estrada, S., Eriksson, J., Asplund, V., Orlova, A., . . . Odell, L. (2016). Synthesis of 11C-labelled Sulfonyl Carbamates via a Multicomponent Reaction Employing Sulfonyl Azides, Alcohols and [11C]CO. ChemistryOpen, 58(3), 566-573
Open this publication in new window or tab >>Synthesis of 11C-labelled Sulfonyl Carbamates via a Multicomponent Reaction Employing Sulfonyl Azides, Alcohols and [11C]CO
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2016 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 58, no 3, p. 566-573Article in journal (Refereed) Accepted
Abstract [en]

Herein we describe the development of new methodologyfocusing on 11C-labelling of sulfonyl carbamates in a multicomponentreaction comprising a sulfonyl azide, an alkyl alcohol and [11C]CO. Anumber of 11C-labelled sulfonyl carbamates were synthesised andisolated, and the developed methodology was then applied in thepreparation of a biologically active molecule. The target compoundwas obtained in 18±8% isolated radiochemical yield and wasevaluated for binding properties in a tumor cell assay, as well asundergoing in vivo biodistribution and imaging studies. Thisrepresents the first successful radiolabelling of C21, a non-peptideangiotensin II receptor subtype 2 agonist currently in clinical trials.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-296406 (URN)
Available from: 2016-06-16 Created: 2016-06-16 Last updated: 2017-11-28
Stevens, M. Y., Chow, S. Y., Estrada, S., Eriksson, J., Asplund, V., Orlova, A., . . . Odell, L. R. (2016). Synthesis of C-11-labeled Sulfonyl Carbamates through a Multicomponent Reaction Employing Sulfonyl Azides, Alcohols, and [C-11]CO. ChemistryOpen, 5(6), 566-573
Open this publication in new window or tab >>Synthesis of C-11-labeled Sulfonyl Carbamates through a Multicomponent Reaction Employing Sulfonyl Azides, Alcohols, and [C-11]CO
Show others...
2016 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 5, no 6, p. 566-573Article in journal (Refereed) Published
Abstract [en]

We describe the development of a new methodology focusing on C-11-labeling of sulfonyl carbamates in a multicomponent reaction comprised of a sulfonyl azide, an alkyl alcohol, and [C-11] CO. A number of C-11-labeled sulfonyl carbamates were synthesized and isolated, and the developed methodology was then applied in the preparation of a biologically active molecule. The target compound was obtained in 24 +/- 10% isolated radiochemical yield and was evaluated for binding properties in a tumor cell assay; in vivo biodistribution and imaging studies were also performed. This represents the first successful radiolabeling of a non-peptide angiotensin II receptor subtype 2 agonist, C21, currently in clinical trials for the treatment of idiopathic pulmonary fibrosis.

Keywords
AT(2)R agonists, multicomponent reactions, radiochemistry, sulfonyl azides, sulfonyl carbamates
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-316971 (URN)10.1002/open.201600091 (DOI)000393071500012 ()28032026 (PubMedID)
Funder
Carl Tryggers foundation , CTS13:333 CTS14:356Swedish Cancer Society, 2014/474Swedish Research Council, 2015-02509
Available from: 2017-03-08 Created: 2017-03-08 Last updated: 2018-01-13Bibliographically approved
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