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• W2022128141 abstract "It has been observed that reported 5-HT1D 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-HT1D receptor. The size of the lipophilic alkyl group at the 5-position of the indole has significant impact on the 5-HT1D 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 (Ki < 1 nM) and moderate receptor selectivity in comparison with known antimigraine agents such as sumatriptan, naratriptan, rizatriptan, and VML-251." @default.
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• W2022128141 date "1999-01-27" @default.
• W2022128141 modified "2023-10-13" @default.
• W2022128141 title "<i>N</i>-Methyl-5-<i>tert</i>-butyltryptamine: A Novel, Highly Potent 5-HT_1D Receptor Agonist" @default.
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• W2022128141 doi "https://doi.org/10.1021/jm9805945" @default.
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