3764-94-1

Usage

Uses

Used in Pharmaceutical Research and Development:
5-Chlorotryptamine hydrochloride is utilized as a research chemical to investigate its pharmacological properties and potential therapeutic effects. Its role as a serotonin receptor agonist makes it a valuable tool for studying the central nervous system and the mechanisms underlying mood and behavior regulation.
Used in Treatment of Depression and Anxiety Disorders:
In the field of psychiatry, 5-chlorotryptamine hydrochloride is considered for its potential use in treating depression and anxiety disorders. Its agonistic action on serotonin receptors suggests that it may help alleviate symptoms associated with these conditions by modulating neurotransmitter activity in the brain.
Used in Neuroscientific Studies:
5-Chlorotryptamine hydrochloride serves as an important compound in neuroscientific research, where it is employed to explore the intricate workings of the serotonergic system. Understanding its effects can contribute to the development of new treatments for a range of neurological and psychiatric disorders.
Used in Drug Development for Mood Disorders:
5-CHLOROTRYPTAMINE HYDROCHLORIDE is also used in the development of new drugs targeting mood disorders. By examining the interactions of 5-chlorotryptamine hydrochloride with serotonin receptors, researchers can identify novel pathways and mechanisms that could be leveraged in the creation of more effective medications.
Used in Toxicological and Safety Assessments:
In the context of drug development, 5-chlorotryptamine hydrochloride is utilized in toxicological studies to assess the safety and potential side effects of this psychoactive substance. This ensures that any therapeutic use is balanced with an understanding of its risks.

InChI:InChI=1/C10H11ClN2/c11-8-1-2-10-9(5-8)7(3-4-12)6-13-10/h1-2,5-6,13H,3-4,12H2

Upstream product

• 98993-95-4 (E)-5-chloro-3-(2-nitroethenyl)-1H-indole 
• 103795-47-7 3-(2-aminoethyl)-5-chloro-1H-indole-2-carboxylic acid 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 151-56-4 ethyleneimine 
• 17422-32-1 5-chloro-1H-indole 
• 1016-35-9 2-(5-chloro-1H-indol-3-yl)-2-oxo-acetamide 
• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 55747-68-7 N-[2-(5-chloro-indol-3-yl)-ethyl]-phthalimide 
• 81630-83-3 2-(5-chloro-1H-indol-3-yl)acetonitrile 
• 98993-95-4 5-chloro-3-(2-nitrovinyl)indole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 54322-20-2 4-chloro-1-hydroxy-1-butanesulfonate sodium 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 

Downstream Products

• 174727-65-2 2-[5-Chloro-1-(2,5-dimethyl-benzyl)-1H-indol-3-yl]-ethylamine 
• 174727-67-4 2-[5-Chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-ethylamine 
• 79087-58-4 N-Acetyl-5-Chloro-Tryptamine 
• 22120-32-7 2-(5-chloro-1H-indol-3-yl)-N, N-dimethylethanamine 
• 859163-70-5 N-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-nitrobenzenesulfonylamide 
• 871586-85-5 2-acetyl-6-chloro-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid 
• 65285-58-7 vincantril 
• 859163-72-7 6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 859163-71-6 N-(1-benzyloxyallyl)-N-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-nitrobenzenesulfonylamide 
• 859163-73-8 1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone 
• 1054650-35-9 (3aS,4S,6R,6aR)-6-(6-{2-[5-Chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid cyclopropylamide 
• 1014700-18-5 C₁₈H₁₄ClF₃N₂O₂ 
• 1355077-82-5 C₂₆H₁₉Cl₂N₃O₂ 
• 1421696-99-2 6-chloro-9-tosyl-3,4-dihydro-β-carbolin 

Relevant academic research and scientific papers

Integrating carbon-halogen bond formation into medicinal plant metabolism

Halogenation, which was once considered a rare occurrence in nature, has now been observed in many natural product biosynthetic pathways. However, only a small fraction of halogenated compounds have been isolated from terrestrial plants. Given the impact that halogenation can have on the biological activity of natural products, we reasoned that the introduction of halides into medicinal plant metabolism would provide the opportunity to rationally bioengineer a broad variety of novel plant products with altered, and perhaps improved, pharmacological properties. Here we report that chlorination biosynthetic machinery from soil bacteria can be successfully introduced into the medicinal plant Catharanthus roseus (Madagascar periwinkle). These prokaryotic halogenases function within the context of the plant cell to generate chlorinated tryptophan, which is then shuttled into monoterpene indole alkaloid metabolism to yield chlorinated alkaloids. A new functional group-a halide-is thereby introduced into the complex metabolism of C. roseus, and is incorporated in a predictable and regioselective manner onto the plant alkaloid products. Medicinal plants, despite their genetic and developmental complexity, therefore seem to be a viable platform for synthetic biology efforts.

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

1-BENZYLSPIRO[PIPERIDINE-4,1′-PYRIDO[3,4-b]indole] ‘co-potentiators’ for minimal function CFTR mutants

We previously identified a spiro [piperidine-4,1-pyrido [3,4-b]indole] class of co-potentiators that function in synergy with existing CFTR potentiators such as VX-770 or GLGP1837 to restore channel activity of a defined subset of minimal function cystic fibrosis transmembrane conductance regulator (CFTR) mutants. Here, structure-activity studies were conducted to improve their potency over the previously identified compound, 20 (originally termed CP-A01). Targeted synthesis of 37 spiro [piperidine-4,1-pyrido [3,4-b]indoles] was generally accomplished using versatile two or three step reaction protocols with each step having high efficiency. Structure-activity relationship studies established that analog 2i, with 6′-methoxyindole and 2,4,5-trifluorobenzyl substituents, had the greatest potency for activation of N1303K-CFTR, with EC50 ～600 nM representing an ～17-fold improvement over the original compound identified in a small molecule screen.

Anti-cancer indole alkaloid compound, preparation method and application thereof

The invention relates to an anti-cancer compound, which is an indole alkaloid series compound and has a general formula (I). Indole alkaloids have a very good inhibitory effect on multiple solid tumors, such as human breast cancer cells, and further have an inhibitory effect on tumor growth. The compound has an inhibitory effect on the growth of cancer cells, but has no inhibitory effect on the growth of normal cells. The compound can be used alone or in combination with other drugs.

Design, synthesis and biological evaluation of tryptamine salicylic acid derivatives as potential antitumor agents

A series of tryptamine salicylic acid derivatives were synthesized and their antiproliferative activity against MGC-803, MCF-7, HepG2, A549 and HeLa cell lines was evaluated. The structure-activity relationship (SAR) study revealed that different substitutions of the C5 and C3′-C5′ positions have certain effects on the anti-proliferation activity. The growth assay revealed that N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide (E20) showed the most potent and broad-spectrum anticancer inhibition of all the cell lines evaluated, and was only more potent than 5-Fu for the gastric cancer cell line. Preliminary studies indicated that compound E20 could inhibit colony formation and migration of MGC-803 cells. The flow cytometry (FCM) results showed that compound E20 arrested the cell cycle in the G2/M phase and induced apoptosis of MGC-803 cells in a concentration-dependent manner. In addition, the western blot results showed that E20 can down-regulate the expression of hexokinase 2. Our studies suggest that the framework of N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide may be consider as a new type of chemical for designing effective anti-cancer drugs targeting gastric cancer cells.

Facile in Vitro Biocatalytic Production of Diverse Tryptamines

Tryptamines are a medicinally important class of small molecules that serve as precursors to more complex, clinically used indole alkaloid natural products. Typically, tryptamine analogues are prepared from indoles through multistep synthetic routes. In the natural world, the desirable tryptamine synthon is produced in a single step by l-tryptophan decarboxylases (TDCs). However, no TDCs are known to combine high activity and substrate promiscuity, which might enable a practical biocatalytic route to tryptamine analogues. We have now identified the TDC from Ruminococcus gnavus as the first highly active and promiscuous member of this enzyme family. RgnTDC performs up to 96 000 turnovers and readily accommodates tryptophan analogues with substituents at the 4, 5, 6, and 7 positions, as well as alternative heterocycles, thus enabling the facile biocatalytic synthesis of >20 tryptamine analogues. We demonstrate the utility of this enzyme in a two-step biocatalytic sequence with an engineered tryptophan synthase to afford an efficient, cost-effective route to tryptamines from commercially available indole starting materials.

Indole derivative and uses thereof

The present invention relates to an indole derivative and uses thereof, wherein the compound and the pharmaceutical composition comprising the compound can be used for antagonizing orexin receptors. The present invention further relates to a method for preparing the compound and the pharmaceutical composition, and uses of the compound and the pharmaceutical composition in treatment or prevention of diseases associated with orexin receptors.

Directed evolution of RebH for catalyst-controlled halogenation of indole C-H bonds

RebH variants capable of chlorinating substituted indoles ortho-, meta-, and para-to the indole nitrogen were evolved by directly screening for altered selectivity on deuterium-substituted probe substrates using mass spectrometry. This systematic approach allowed for rapid accumulation of beneficial mutations using simple adaptive walks and should prove generally useful for altering and optimizing the selectivity of C-H functionalization catalysts. Analysis of the beneficial mutations showed that structure-guided selection of active site residues for targeted mutagenesis can be complicated either by activity/selectivity tradeoffs that reduce the possibility of detecting such mutations or by epistatic effects that actually eliminate the benefits of a mutation in certain contexts. As a corollary to this finding, the precise manner in which the beneficial mutations identified led to the observed changes in RebH selectivity is not clear. Docking simulations suggest that tryptamine binds to these variants as tryptophan does to native halogenases, but structural studies will be required to confirm these models and shed light on how particular mutations impact tryptamine binding. Similar directed evolution efforts on other enzymes or artificial metalloenzymes could enable a wide range of C-H functionalization reactions.

Synthesis and structureactivity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands

5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structureactivity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the Ki of 23.4 and 20.5nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

The discovery of tetrahydro-β-carbolines as inhibitors of the kinesin Eg5

A series of tetrahydro-β-carbolines were identified by HTS as inhibitors of the kinesin Eg5. Molecular modeling and medicinal chemistry techniques were employed to explore the SAR for this series with a focus of removing potential metabolic liabilities and improving cellular potency.