Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 13, Issue 14, Pages 4434-4442Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2005.04.047
Keywords
fancy bioisosteres; dopamine; D3; palladium catalyzed cross coupling
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Structural variations of the lead compound FAUC 88 led to dopaminergic enynes with an extended pi-system when Pd-catalyzed cross coupling reactions were employed for the key reaction steps. The dienyne 9b displayed substantial affinity for the dopamine receptor subtype D3 and remarkable selectivity over D4. Compared to FAUC 88, the novel fancy bioisostere 9b displayed reduced ligand efficacy. DFT-based conformational analysis of the test compound 9b, including the calculation of diagnostic magnetic shielding properties and their comparison with experimentally derived NMR data, indicated a clear energetic preference for the s-trans geometry of the diene substructure. (c) 2005 Elsevier Ltd. All rights reserved.
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