Expedient on-resin synthesis of peptidic benzimidazoles
Copyright © 2018. Published by Elsevier Ltd..
The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles - an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2018 |
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| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:28 |
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| Enthalten in: |
Bioorganic & medicinal chemistry letters - 28(2018), 16 vom: 01. Sept., Seite 2679-2681 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Bird, Michael J [VerfasserIn] |
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| Links: |
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| Themen: |
Anthelmintics |
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| Anmerkungen: |
Date Completed 16.01.2019 Date Revised 09.01.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bmcl.2018.04.062 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM283865903 |
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| 500 | |a Date Revised 09.01.2021 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2018. Published by Elsevier Ltd. | ||
| 520 | |a The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles - an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, N.I.H., Extramural | |
| 650 | 4 | |a Anthelmintics | |
| 650 | 4 | |a Antifungals | |
| 650 | 4 | |a Antimicrobials | |
| 650 | 4 | |a Benzimidazoles | |
| 650 | 4 | |a Peptide benzimidazoles | |
| 650 | 4 | |a Peptide therapeutics | |
| 650 | 4 | |a SPPS | |
| 650 | 7 | |a Benzimidazoles |2 NLM | |
| 650 | 7 | |a Oligopeptides |2 NLM | |
| 650 | 7 | |a Resins, Synthetic |2 NLM | |
| 700 | 1 | |a Silvestri, Anthony P |e verfasserin |4 aut | |
| 700 | 1 | |a Dawson, Philip E |e verfasserin |4 aut | |
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