Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT2A receptor
Graphical abstract
The synthesis and 5-HT2A receptor affinities of a series of methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives are reported. Molecular modeling techniques are used to elucidate probable binding modes for the compounds.
Section snippets
Acknowledgments
This work was supported by United States Public Health Service Grant R01-MH57969 (RBW), R01-MH57635 (BLR), K02-MH01366 (BLR) and R01-MH61887 (BLR), U19-MH82441 (BLR) and the NIMH Psychoactive Drug Screening Program (BLR).
References and notes (21)
- et al.
Bioorg. Med. Chem. Lett.
(2001) - et al.
Eur. J. Pharmacol.
(1999) - et al.
J. Pharmacol. Sci.
(2006) - et al.
Bioorg. Med. Chem. Lett.
(2001) - et al.
Neuropharmacology
(2006) - et al.
Methods Neurosci.
(1995) - et al.
J. Mol. Biol.
(1993) - et al.
J. Mol. Biol.
(1995) - et al.
J. Mol. Biol.
(1997) - et al.
Curr. Top. Med. Chem.
(2002)
Cited by (10)
Addressing polar solvent challenges in the heterogenization of palladium catalysed Hayashi-Miyaura reaction on polymer support
2023, Reactive and Functional PolymersMild Three-Step Consecutive C-H Activations
2022, Organic Letters(4-Phenoxyphenyl)tetrazolecarboxamides and related compounds as dual inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL)
2013, European Journal of Medicinal ChemistryCitation Excerpt :The preparation of the oxazolidinone substituted target compound 19 started from 4-phenoxybenzaldehyde, which was first converted to the acetonitrile 17 by reaction with trimethylsilyl cyanide (Scheme 2) [18]. Reduction of this intermediate by LiAlH4 [19] led to the 2-aminoethanol 18. Formation of the oxazolidinone ring was finally achieved using trichloromethyl chloroformate [20].
9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT<inf>2A</inf> and H<inf>1</inf> receptor binding sites
2010, Bioorganic and Medicinal Chemistry LettersMolecular basis for cis-urocanic acid as a 5-HT<inf>2A</inf> receptor agonist
2009, Bioorganic and Medicinal Chemistry Letters