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A convenient transesterification method for synthesis of AT2 receptor ligands with improved stability in human liver microsomes
Uppsala University, Science for Life Laboratory, SciLifeLab. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmacy. Uppsala University, Science for Life Laboratory, SciLifeLab.
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2018 (English)In: Bioorganic & Medicinal Chemistry Letters, ISSN 0960-894X, E-ISSN 1090-2120, Vol. 28, no 3, p. 519-522Article in journal (Refereed) Published
Abstract [en]

A series of AT2R ligands have been synthesized applying a quick, simple, and safetransesterification-type reaction whereby the sulfonyl carbamate alkyl tail ofthe selective AT2R antagonist C38 was varied. Furthermore, a limited number ofcompounds where acyl sulfonamides and sulfonyl ureas served as carboxylic acidbioisosteres were synthesized and evaluated. By reducing the size of the alkylchain of the sulfonyl carbamates, ligands 7a and 7b were identified withsignificantly improved in vitro metabolic stability in both human and mouse livermicrosomes as compared to C38 while retaining the AT2R binding affinity andAT2R/AT1R selectivity. Eight of the compounds synthesized exhibit an improvedstability in human microsomes as compared to C38.

Place, publisher, year, edition, pages
Elsevier, 2018. Vol. 28, no 3, p. 519-522
Keywords [en]
AT(2)R antagonists, Angiotensin II type 2 receptor antagonists, Liver microsomes, Sulfonyl carbamates, Transesterification
National Category
Organic Chemistry Medicinal Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-343592DOI: 10.1016/j.bmcl.2017.11.042ISI: 000424285600053PubMedID: 29279275OAI: oai:DiVA.org:uu-343592DiVA, id: diva2:1186364
Funder
Science for Life Laboratory - a national resource center for high-throughput molecular bioscienceAvailable from: 2018-02-28 Created: 2018-02-28 Last updated: 2018-04-04Bibliographically approved

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Wannberg, JohanIsaksson, RebeckaBacklund, MariaSävmarker, JonasHallberg, MathiasLarhed, Mats

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Wannberg, JohanIsaksson, RebeckaBremberg, UlfBacklund, MariaSävmarker, JonasHallberg, MathiasLarhed, Mats
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Science for Life Laboratory, SciLifeLabPreparative Medicinal ChemistryDepartment of PharmacyDepartment of Medicinal ChemistryDepartment of Pharmaceutical Biosciences
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Bioorganic & Medicinal Chemistry Letters
Organic ChemistryMedicinal Chemistry

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