Synthesis of the calcilytic ligand NPS 2143
(R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessme...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.154 |
| _version_ | 1818675442670895104 |
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| author | Henrik Johansson Thomas Cailly Alex Rojas Bie Thomsen Hans Bräuner-Osborne Daniel Sejer Pedersen |
| author_facet | Henrik Johansson Thomas Cailly Alex Rojas Bie Thomsen Hans Bräuner-Osborne Daniel Sejer Pedersen |
| author_sort | Henrik Johansson |
| collection | DOAJ |
| description | (R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent optical purity (er > 99:1) as demonstrated by chiral HPLC and the pharmacological profile for (R)-3 is in full accordance with that reported in the literature. |
| first_indexed | 2024-12-17T08:27:39Z |
| format | Article |
| id | doaj.art-ccfa7cc8e54a496682b57ba096ed7e10 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T08:27:39Z |
| publishDate | 2013-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ccfa7cc8e54a496682b57ba096ed7e102022-12-21T21:56:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-07-01911383138710.3762/bjoc.9.1541860-5397-9-154Synthesis of the calcilytic ligand NPS 2143Henrik Johansson0Thomas Cailly1Alex Rojas Bie Thomsen2Hans Bräuner-Osborne3Daniel Sejer Pedersen4Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, DenmarkDepartment of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, DenmarkDepartment of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, DenmarkDepartment of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, DenmarkDepartment of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark(R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent optical purity (er > 99:1) as demonstrated by chiral HPLC and the pharmacological profile for (R)-3 is in full accordance with that reported in the literature.https://doi.org/10.3762/bjoc.9.154epoxidesGPCRNPS 2143nucleophilic aromatic substitutionpyrylium chemistry |
| spellingShingle | Henrik Johansson Thomas Cailly Alex Rojas Bie Thomsen Hans Bräuner-Osborne Daniel Sejer Pedersen Synthesis of the calcilytic ligand NPS 2143 Beilstein Journal of Organic Chemistry epoxides GPCR NPS 2143 nucleophilic aromatic substitution pyrylium chemistry |
| title | Synthesis of the calcilytic ligand NPS 2143 |
| title_full | Synthesis of the calcilytic ligand NPS 2143 |
| title_fullStr | Synthesis of the calcilytic ligand NPS 2143 |
| title_full_unstemmed | Synthesis of the calcilytic ligand NPS 2143 |
| title_short | Synthesis of the calcilytic ligand NPS 2143 |
| title_sort | synthesis of the calcilytic ligand nps 2143 |
| topic | epoxides GPCR NPS 2143 nucleophilic aromatic substitution pyrylium chemistry |
| url | https://doi.org/10.3762/bjoc.9.154 |
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