- N-methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT(1D) receptor agonist
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It has been observed that reported 5-HT(1D) receptor agonists have at least one heteroatom (N, O, or S) on the 5-substituent of the indole. This has led to the hypothesis that a 5-substituent capable of participating in hydrogen bonding is critical for conveying high affinity. This article describes the synthesis and biological evaluation of a new series of 5- alkyltryptamine analogues, which does not have a heteroatom in the 5- substituent group. In contrast to the hypothesis, 5-alkyltryptamines all exhibit high binding affinities for the human 5-HT(1D) receptor. The size of the lipophilic alkyl group at the 5-position of the indole has significant impact on the 5-HT(1D) binding affinity. Compounds with a tert-butyl group at the 5-position such as 9d, 10, and 11 were identified. These analogues display high binding affinity (K(i) 1 nM) and moderate receptor selectivity in comparison with known antimigraine agents such as sumatriptan, naratriptan, rizatriptan, and VML-251.
- Xu, Yao-Chang,Schaus, John M.,Walker, Clint,Krushinski, Joe,Adham, Nika,Zgombick, John M.,Liang, Sidney X.,Kohlman, Dan T.,Audia, James E.
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p. 526 - 531
(2007/10/03)
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- INTERMEDIATES TO TETRAHYDRO-BETA-CARBOLINES
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3-Ethanamine and 3-ethanamine related compounds are provided that are useful intermediates and have beneficial central nervous system activity.
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- METHOD FOR TREATING 5HT2B RECEPTOR RELATED CONDITIONS
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The present invention provides methods for binding a 5-HT 2B receptor in mammals using a both known and novel compounds. Further, the invention provides a method for treating or preventing 5-HT 2B related conditions. Finally, the invention provides an article of manufacture.
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- TETRAHYDRO-PYRIDO-INDOLE
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The present invention provides pentacyclic pyrido[3,4-b] indoles having useful central nervous system activity.
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- Tetrahydro-β-carbolines
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The present invention provides tetrahydro-betacarboline compounds having useful central nervous system activity.
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- Tetrahydro-pyrido-indole
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The present invention provides a new Pictet-Spengler process useful for preparing tetrahydro-beta-carboline compounds.
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- Formation of Head-to-Tail and Side-by-Side Aggregates of Photochromic Spiropyrans in Bilayer Membrane
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Aggregation phenomenon and thermal isomerization behaviors of photochromic spiropyran (SP) compounds in dioctadecyldimethylammonium (2C18N+2C1) bilayer membrane are reported.Spiropyran compounds having two alkyl chains form J-aggregate (head-to-tail) or H-aggregate (side-by-side) in the bilayer when they are converted to the photoinduced merocyanine form by UV light (PMC).The type of the aggregate depends on the chemical structure of this photochromic molecule.One type of PMC forms J-aggregate (J-PMC) at the mixing molar ratio of spiropyran to 2C18N+2C1 (R) ofmore than 0.01, and the other type forms H-aggregate (H-PMC) at R larger than 0.02.It is suggested in comparison with other isotropic media that an orientation effect of the anisotropic environment formed by the bilayer is essential for the controlled aggregate formation.J-PMC is stable in the bilayer regardless of the crystal liquid crystal phase change, and H-PMC, on the other hand, is formed only in the crystal (gel) phase.Aggregation retards the rate of the thermal isomerization (PMC-SP) to large extents, depending on the aggregation type.This paper reports, for the first time, the aggregation phenomenon of photochromic spiropyran compounds in the bilayer matrix.
- Seki, Takahiro,Ichimura, Kunihiro
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p. 3769 - 3775
(2007/10/02)
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