- 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities
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A series of novel ligands for the serotonin 5-HT2A/C receptor subtype bearing the 2-phenylethylamine pharmacophore was synthesized and assayed for its 5-HT2A receptor binding affinity. As the 4′-arylsubstituted 2-(2,5-dimethoxyphenyl
- Trachsel, Daniel,Nichols, David E.,Kidd, Stephanie,Hadorn, Marcel,Baumberger, Franz
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experimental part
p. 692 - 704
(2010/04/23)
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- Compounds with medicinal effects due to interaction with the glucocorticoid receptor
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The invention provides for compounds having the structure according to the formula I
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Page/Page column 15
(2010/11/27)
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- HYDROXY-BIPHENYL-CARBALDEHYDE OXIME DERIVATIVES AND THEIR USE AS ESTROGENIC AGENTS
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This invention provides estrogen receptor modulators having the structure formula (I): wherein R1 to R6 and R8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.
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- ERβ ligands. Part 2: Synthesis and structure-activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives
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A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-β (ERβ). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radioligand binding assay of between 8-35nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERβ selective, respectively).
- Yang, Cuijian,Edsall Jr., Richard,Harris, Heather A.,Zhang, Xiaochun,Manas, Eric S.,Mewshaw, Richard E.
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p. 2553 - 2570
(2007/10/03)
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- A Fluorescent Self-Amplifying Wavelength-Responsive Sensory Polymer for Fluoride Ions
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A glowing response: Novel fluoride-selective sensors, utilizing fluoride-induced lactonization to highly fluorescent coumarin derivatives, are reported. The incorporation of this sensory system into a conjugated polymer amplifies the fluorescence response
- Kim, Tae-Hyun,Swager, Timothy M.
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p. 4803 - 4806
(2007/10/03)
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- 1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character
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Certain phenylethylamines, such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; 1a), are high-affinity 5-HT2 agonists. Previous structure - affinity studies have concluded that both the 2,5-dimethoxy substitution pattern and the nature of substituents at the 4-position are important determinants of high affinity. We recently demonstrated that replacement of the bromo group of DOB with a 3-(phenyl)propyl substituent results in retention of affinity and that, counter to established structure - affinity relationships, the 2,5-dimethoxy substitution pattern is no longer a requirement for the binding. The present investigation extends these findings by examining a series of analogues, 3, lacking a 5-methoxy group. It was additionally found that shifting the phenylalkyl substituent from the 4- to the 5-position (e.g., 4i) also results in retention of affinity. For example, 1-(2-methoxy-5-(3-phenylpropyl)-2-aminopropane (6; the α-methyl derivative of 4i) binds at 5-HT2A receptors with high affinity (Ki = 13 nM) and possesses 5-HT2A antagonist character. Thus, not only is the 2,5-dimethoxy substitution pattern not a requirement for the binding of certain phenylethylamines at 5-HT2A receptors, the presence of a 4-position substituent (previously thought to serve as a modulator of affinity of DOB-like agents) is also not required. Striking differences in the 5-HT2A binding requirements of the present compounds as compared to DOB-like agents suggest multiple substituent-dependent modes of binding.
- Rangisetty,Dukat,Dowd,Herrick-Davis,DuPre,Gadepalli,Teitler,Kelley,Sharif,Glennon
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p. 3283 - 3291
(2007/10/03)
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- 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists
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Phenylalkylamines such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; 1a) and its corresponding iodo derivative DOI (2) are commonly used 5-HT2 serotonin agonists. Previous studies have established that the 2,5-dimethoxy substitution p
- Dowd,Herrick-Davis,Egan,DuPre,Smith,Teitler,Glennon
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p. 3074 - 3084
(2007/10/03)
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- Trisubstituted biphenyls
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Antihypertensive and antiatherosclerotic trisubstituted biphenyls of the formula STR1 in which R1 represents a carboxyl radical or represents a C1 -C8 -alkoxycarbonyl radical, R2 represents straight-chain or bra
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