Synthesis and biological evaluation of 4-nitroindole derivatives as 5-HT2A receptor antagonists

[Display omitted] A novel series of 4-nitroindole sulfonamides containing a methyleneamino-N,N-dimethylformamidine were prepared. The binding of these compounds to 5-HT2A and 5-HT2C was evaluated, and most of the compounds showed IC50 values of less than 1μM, and exhibited high selectivity for the 5...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2015-03, Vol.23 (6), p.1313-1320
Hauptverfasser:	Hayat, Faisal, Viswanath, Ambily Nath Indu, Pae, Ae Nim, Rhim, Hyewhon, Park, Woo-Kyu, Choo, Hea-Young Park
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Nitroindole 5-HT2A 5-HT2C 5-HT6 receptor Dose-Response Relationship, Drug Humans Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Methyleneamino-N,N-dimethylformamidine group Molecular Structure Nitro Compounds - chemical synthesis Nitro Compounds - chemistry Nitro Compounds - pharmacology Receptor, Serotonin, 5-HT2A - metabolism Recombinant Proteins - metabolism Serotonin 5-HT2 Receptor Antagonists - chemical synthesis Serotonin 5-HT2 Receptor Antagonists - chemistry Serotonin 5-HT2 Receptor Antagonists - pharmacology Structure-Activity Relationship Sulfonamides
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Zusammenfassung:	[Display omitted] A novel series of 4-nitroindole sulfonamides containing a methyleneamino-N,N-dimethylformamidine were prepared. The binding of these compounds to 5-HT2A and 5-HT2C was evaluated, and most of the compounds showed IC50 values of less than 1μM, and exhibited high selectivity for the 5-HT2C receptor. However, little selectivity was observed in the functional assay for 5-HT6 receptors. The computational modeling studies further validated the biological results and also demonstrated a reasonable correlation between the activity of compounds and the mode of superimposition with specified pharmacophoric features.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2015.01.032