Selective functionalization of the 1H-imidazo[1,2-b]pyrazole scaffold. A new potential non-classical isostere of indole and a precursor of push-pull dyes
This journal is © The Royal Society of Chemistry..
We report the selective functionalization of the 1H-imidazo[1,2-b]pyrazole scaffold using a Br/Mg-exchange, as well as regioselective magnesiations and zincations with TMP-bases (TMP = 2,2,6,6-tetramethylpiperidyl), followed by trapping reactions with various electrophiles. In addition, we report a fragmentation of the pyrazole ring, giving access to push-pull dyes with a proaromatic (1,3-dihydro-2H-imidazol-2-ylidene)malononitrile core. These functionalization methods were used in the synthesis of an isostere of the indolyl drug pruvanserin. Comparative assays between the original drug and the isostere showed that a substitution of the indole ring with a 1H-imidazo[1,2-b]pyrazole results in a significantly improved solubility in aqueous media.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:12 |
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| Enthalten in: |
Chemical science - 12(2021), 39 vom: 13. Okt., Seite 12993-13000 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Schwärzer, Kuno [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 03.04.2024 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d1sc04155j |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM332835707 |
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| 245 | 1 | 0 | |a Selective functionalization of the 1H-imidazo[1,2-b]pyrazole scaffold. A new potential non-classical isostere of indole and a precursor of push-pull dyes |
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| 500 | |a published: Electronic-eCollection | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a This journal is © The Royal Society of Chemistry. | ||
| 520 | |a We report the selective functionalization of the 1H-imidazo[1,2-b]pyrazole scaffold using a Br/Mg-exchange, as well as regioselective magnesiations and zincations with TMP-bases (TMP = 2,2,6,6-tetramethylpiperidyl), followed by trapping reactions with various electrophiles. In addition, we report a fragmentation of the pyrazole ring, giving access to push-pull dyes with a proaromatic (1,3-dihydro-2H-imidazol-2-ylidene)malononitrile core. These functionalization methods were used in the synthesis of an isostere of the indolyl drug pruvanserin. Comparative assays between the original drug and the isostere showed that a substitution of the indole ring with a 1H-imidazo[1,2-b]pyrazole results in a significantly improved solubility in aqueous media | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Rout, Saroj K |e verfasserin |4 aut | |
| 700 | 1 | |a Bessinger, Derya |e verfasserin |4 aut | |
| 700 | 1 | |a Lima, Fabio |e verfasserin |4 aut | |
| 700 | 1 | |a Brocklehurst, Cara E |e verfasserin |4 aut | |
| 700 | 1 | |a Karaghiosoff, Konstantin |e verfasserin |4 aut | |
| 700 | 1 | |a Bein, Thomas |e verfasserin |4 aut | |
| 700 | 1 | |a Knochel, Paul |e verfasserin |4 aut | |
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