Psilocin analogs. III. Synthesis of 5‐methoxy‐ and 5‐hydroxy‐1,2,3,4‐tetrahydro‐9<i>H</i>‐pyrido[3,4‐<i>b</i>]indoles

Repke, David B.; Ferguson, Wilfred J.

doi:10.1002/jhet.5570190428

Cited by 33 publications

(17 citation statements)

References 26 publications

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“…In general, few of the compounds displayed higher affinity for 5-HT 2C receptors versus 5-HT 2A receptors. However, limited bulk at the 5-position resulted in compounds (i.e., 25,26) with up to 20-fold 5-HT 2C selectivity.…”

Section: -Ht 2c Binding 20mentioning

confidence: 98%

Binding of β-Carbolines at 5-HT 2 serotonin receptors

Grella

Teitler

Smith

et al. 2003

Bioorganic & Medicinal Chemistry Letters

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Section: -Ht 2c Binding 20mentioning

confidence: 98%

Binding of β-Carbolines at 5-HT 2 serotonin receptors

Grella

Teitler

Smith

et al. 2003

Bioorganic & Medicinal Chemistry Letters

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“…Following the early work of Flaugh et al [48], most syntheses are based on classic procedures [49][50][51]. The best route to 5-methoxyindole (4) is probably via the Repke-Ferguson [55] modification of the Leimgruber-Batcho reaction [56], Fig. 5-Methoxytryptamine (3a) can be prepared by the Grandberg-Bobrova [52] modification of the Fischer indole synthesis, but has problems with further alkylation [53,54].…”

Section: Indole Benzo[b]thiophene Benzo[b]furan Benzimidazoles Inmentioning

confidence: 99%

Synthesis of Compounds as Melatonin Agonists and Antagonists

Garratt¹,

Tsotinis

2007

MRMC

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The functions of melatonin, the hormone of the pineal gland, are of considerable current interest. Synthetic melatonin analogues as agonists and antagonists have been explored in some detail and the molecule can be considered as consisting of an indole core, acting mainly as a spacer, and the 5-methoxyl and 3-amidoethyl side chains acting as the functional components, as originally proposed by Heward and Hadley. This review focuses on the synthetic routes to these melatonin analogues, first of the core, then of the substituents that have been attached to the core, and finally those compounds with restricted conformations and those that are chiral. The importance of the various factors involved in the activity of the compounds as agonist or antagonists is indicated, as is the difference in activity of enantiomers.

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“…One of the synthetic routes for the production of 5-methoxyindole (4) is via the Leimgruber-Batcho reaction [33], modified by Repke and Ferguson [34] (Figure 2). A successful side chain functionalization was reported by Ates-Alagoz et al [35] using the Vilsmeier-Haack formylation reaction of 5-methoxyindole (4).…”

Section: Indole and Bioisosteric Derivativesmentioning

confidence: 99%

Synthetic Melatonin Receptor Agonists and Antagonists

Tsotinis¹,

Papanastasiou²

2020

Melatonin - The Hormone of Darkness and Its Therapeutic Potential and Perspectives

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The functions of the pineal hormone melatonin are of intense and continuous interest. Synthetic melatonin receptor analogues, as agonists and antagonists, have been explored, and the molecule can be viewed as consisting of an indole nucleus, acting mainly as a spacer, and the C5-OMe and the C3-ethylamido side chains, acting as pharmacophoric components. The present chapter focuses on the synthetic routes towards these melatonin derivatives, first the aromatic nucleus, then the functionalities that have been introduced to the nucleus, and finally those analogues with restrained conformations and those that are optically active. The importance of the various parameters involved in the agonist and antagonist profile of the compounds is indicated, as is the difference in the action of the chiral melatoninergics.

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Psilocin analogs. III. Synthesis of 5‐methoxy‐ and 5‐hydroxy‐1,2,3,4‐tetrahydro‐9H‐pyrido[3,4‐b]indoles

Abstract: A number of tetrahydro‐β‐carbolines were prepared with oxygen substituents at C‐5. This class of compounds represents a hybrid between two naturally occurring groups of hallucinogenic molecules, the 4‐hydroxytryptamines and the 6‐ and 7‐oxygenated β‐carbolines.

Cited by 33 publications

References 26 publications

Binding of β-Carbolines at 5-HT 2 serotonin receptors

Binding of β-Carbolines at 5-HT 2 serotonin receptors

Synthesis of Compounds as Melatonin Agonists and Antagonists

Synthetic Melatonin Receptor Agonists and Antagonists

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