Evaluation of isotryptamine derivatives at 5-HT2 serotonin receptors

Chang-Fong, Jean; Addo, James K.; Dukat, Małgorzata; Smith, Carol; Mitchell, Nicholas A.; Herrick‐Davis, Katharine; Teitler, Milt; Glennon, Richard A.

doi:10.1016/s0960-894x(01)00713-2

Cited by 34 publications

(11 citation statements)

References 7 publications

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“…18,19 Reaction of the indenyl anion with benzyl chloride afforded nearly equal mixture of products 9 and 10 (Scheme 1). Treatment of the mixture with NaH and reaction with N,N-dimethylaminoethyl chloride can, in theory, result in the formation of three products (i.e., [11][12][13]. Such results have been reported for related compounds.…”

supporting

confidence: 53%

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Binding of isotryptamines and indenes at h5-HT6 serotonin receptors

Kolanoś

Siripurapu

Pullagurla

et al. 2005

Bioorganic & Medicinal Chemistry Letters

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supporting

confidence: 53%

“…Two strategies were employed to address this issue. First, because isotryptamines have been shown to mimic tryptamines at certain 5-HT receptors, 13,14 an isotryptamine analog of 4 (i.e., 5) was examined. Second, the indole nitrogen atom of 4 was replaced by an sp 2 -hybridized carbon atom to afford indene analog 6.…”

mentioning

confidence: 99%

Binding of isotryptamines and indenes at h5-HT6 serotonin receptors

Kolanoś

Siripurapu

Pullagurla

et al. 2005

Bioorganic & Medicinal Chemistry Letters

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“…Agents with high affinity for 5-HT 2C receptors typically possess high affinity for 5-HT 2A receptors and rarely display >10-fold selectivity [15]. While Serotonin (7), the endogenous ligand of the 5-HT receptors, shows some functional selectivity for the 5-HT 2B receptor (Fig.…”

Section: Biased Screening and Discovery Of Pyrroloindolementioning

confidence: 99%

5-HT2C Receptor Agonists for the Treatment of Obesity. Biological and Chemical Adventures

Adams¹,

Bénardeau²,

Bickerdike³

et al. 2004

Chimia

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Obesity is a major risk factor in the development of conditions such as hypertension, hyperglycemia, dyslipidemia, coronary artery disease and cancer. There is increasing evidence suggesting an important role for the 5-HT 2C receptor in appetite control. Collaboration between F. Hoffmann-La Roche Ltd and Vernalis Research Ltd has allowed rapid construction of a solid structure-activity relationship around a pyrroloindole core. A one-pot Sonogashira reaction followed by nucleophilic double cyclisation allows an elegant and expedient route to this central motif. Introduction of a (2S)-aminopropyl group in place of the aminoethyl endogenous ligand side-chain enhanced the affinity at the 5-HT 2C receptor and reduced affinity towards monoamine oxidase enzymes (MAO). Sulfamidate reagents were found to be very effective for the introduction of the 2-aminopropyl moiety in a stereoselective manner. The substitution at position 5 (indole numbering) was found to be crucial for both affinity and selectivity. Pyrroloindoles bearing an alkoxyether in this position exhibit promising pharmacokinetic parameters in rodent and significant reduction of food intake, after per os application.

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“…On the basis of the documented biological properties such as an inhibition of protein kinase C [24], 5-HT 2A , 5-HT 2C agonist [25,26], and antibacterial and antifungal activities [27] of heterocyclic compounds containing the 1,2,3,4-tetrahydropyrazino[1,2-a] indole scaffolds, we became interested in the synthesis of novel fused heterocycles encompassing fused bioactive indole as well as piperazine moieties.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Ugi‐Azide Four‐Component Approach for the Preparation of Novel 1‐(1H‐tetrazol‐5‐yl)‐10‐chloro‐1,2,3,4‐tetrahydropyrazino[1,2‐a] Indoles

Salahi

Ghandi

Abbasi

2019

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The synthesis of novel 1-(1H-tetrazol-5-yl)-10-chloro-1,2,3,4-tetrahydropyrazino[1,2-a] indole derivatives starting from the initially prepared 1-(2-bromoethyl)-3-chloro-1H-indole-2-carbaldehyde is described. A variety of likely biologically relevant pyrazino[1,2-a] indole-based 1,5-disubstituted tetrazoles was obtained in moderate to high yields via an Ugi-azide reaction. These reactions presumably proceed by the imine formation, intramolecular cyclization to iminium ion, and nucleophilic addition tandem reactions, respectively.

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Evaluation of isotryptamine derivatives at 5-HT2 serotonin receptors

Cited by 34 publications

References 7 publications

Binding of isotryptamines and indenes at h5-HT6 serotonin receptors

Binding of isotryptamines and indenes at h5-HT6 serotonin receptors

5-HT2C Receptor Agonists for the Treatment of Obesity. Biological and Chemical Adventures

An Efficient Ugi‐Azide Four‐Component Approach for the Preparation of Novel 1‐(1H‐tetrazol‐5‐yl)‐10‐chloro‐1,2,3,4‐tetrahydropyrazino[1,2‐a] Indoles

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