Halogen substituents on the aromatic moiety of the tetracaine scaffold improve potency of cyclic nucleotide-gated channel block
| Autor: | Evan P. Jackson, Kenneth Melich, Adriana L. Andrade, Jeffrey W. Karpen, Elysia Cuellar, Sarah R. Kirk |
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| Rok vydání: | 2011 |
| Předmět: |
Tetracaine
Chemistry Stereochemistry Organic Chemistry Clinical Biochemistry Cyclic-Nucleotide Gated Channel Cyclic Nucleotide-Gated Cation Channels Pharmaceutical Science Ring (chemistry) Biochemistry Article Retinal rods Halogens Drug Discovery Halogen medicine Molecular Medicine Potency Aromatic moiety Molecular Biology Ion channel medicine.drug |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 21:6417-6419 |
| ISSN: | 0960-894X |
| Popis: | A series of new tetracaine derivatives with substituents on the aromatic ring was prepared and evaluated for block of retinal rod cyclic nucleotide-gated (CNG) channels. Aromatic substitutions had little effect starting with the basic tetracaine scaffold, but electron-withdrawing substituents significantly improved the blocking potency of an octyl-tail derivative of tetracaine. In particular, halogen substitutions at either the 2- or 3-position on the ring resulted in compounds that were up to eight-fold more potent than the parent octyl-tail derivative and up to 50-fold more potent than tetracaine. |
| Databáze: | OpenAIRE |
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