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196965-14-7

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Novel and selective 5-HT(2C/2B) receptor antagonists as potential anxiolytic agents: Synthesis, quantitative structure - Activity relationships, and molecular modeling of substituted 1-(3- pyridylcarbamoyl)indolines
The synthesis, biological activity, and molecular modeling of a novel series of substituted 1-(3-pyridylcarbamoyl)indolines are reported. These compounds are isosteres of the previously published indole urea 1 (SB- 206553) and illustrate the use of aromatic disubstitution as a replacement for fused five-membered rings in the context of 5-HT(2C/2B) receptor antagonists. By targeting a region of space previously identified as sterically allowed at the 5-HT(2C) receptor but disallowed at the 5-HT(2A) receptor, we have identified a number of compounds which are the most potent and selective 5-HT(2C/2B) receptor antagonists yet reported. 46 (SB-221284) was selected on the basis of its overall biological profile for further evaluation as a novel, potential nonsedating anxiolytic agent. A CoMFA analysis of these compounds produced a model with good predictive value and in addition good qualitative agreement with both our 5-HT(2C) receptor model and our proposed binding mode for this class of ligands within that model.
Bromidge, Steven M.,Dabbs, Steven,Davies, David T.,Duckworth, D. Malcolm,Forbes, Ian T.,Ham, Peter,Jones, Graham E.,King, Frank D.,Saunders, Damian V.,Starr, Susannah,Thewlis, Kevin M.,Wyman, Paul A.,Blaney, Frank E.,Naylor, Christopher B.,Bailey, Fiona,Blackburn, Thomas P.,Holland, Vicky,Kennett, Guy A.,Riley, Graham J.,Wood, Martyn D.
p. 1598 - 1612
(2007/10/03)

6-chloro-5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]-5-pyridyl]carbamoyl]- indoline (SB-242084): The first selective and brain penetrant 5-HT(2C) receptor antagonist
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Bromidge,Duckworth,Forbes,Ham,King,Thewlis,Blaney,Naylor,Blackburn,Kennett,Wood,Clarke
p. 3494 - 3496
(2007/10/03)

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Chemical Properties

Boiling Point: 536.2oC at 760 mmHg
Flash Point:278.1oC
Density: 1.43g/cm3
Solubility:DMSO: ~14 mg/mL, soluble
Storage Temp.:Store at +4°C
Vapor Pressure: 1.43E-11mmHg at 25°C
PSA: 70.53000
LogP: 4.55490

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