17403-05-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole is used as a pharmacological agent for its potential as a serotonin receptor agonist, which may have implications in the treatment of various disorders related to serotonin dysregulation.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole serves as a subject of study for understanding its interactions with biological targets and its potential to be developed into a therapeutic agent.
Used in Drug Development:
3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole is utilized in drug development processes to explore its efficacy and safety as a potential new medication, with a focus on its ability to modulate serotonin receptor activity.

Upstream product

• 120-72-9 indole 
• 3612-20-2 1-phenylmethyl-4-piperidone 

Downstream Products

• 179234-89-0 3-(1-benzylpiperidin-4-yl)-1H-indole 
• 56361-85-4 (4-(1H-indol-3-yl)piperidin-1-yl)(phenyl)methanone 
• 17403-09-7 3-(4-piperidinyl)-1H-indole 
• 52157-72-9 3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1-methyl-indole 

Relevant academic research and scientific papers

Synthesis, pharmacological and structural studies of 5-substituted-3-(1-arylmethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as multi-target ligands of aminergic GPCRs

Schizophrenia is a complex disease with not fully understood pathomechanism, involving many neurotransmitters and their receptors. This is why it is best treated with multi-target drugs, such as second generation antipsychotics. Here we present 5-substitu

Exploring the 3-piperidin-4-yl-1H-indole scaffold as a novel antimalarial chemotype

A series of 3-piperidin-4-yl-1H-indoles with building block diversity was synthesized based on a hit derived from an HTS whole-cell screen against Plasmodium falciparum. Thirty-eight compounds were obtained following a three-step synthetic approach and evaluated for anti-parasitic activity. The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. Nevertheless, we were able to identify a new compound (10d) with lead-like properties (MW = 305; cLogP = 2.42), showing antimalarial activity against drug-resistant and sensitive strains (EC50 values ～ 3 μM), selectivity for malaria parasite and no cross-resistance with chloroquine, thus representing a potential new chemotype for further optimization towards novel and affordable antimalarial drugs.

Synthesis and biological evaluation of novel pyrrolidine-2,5-dione derivatives as potential antidepressant agents. Part 1

A series of 3-(1H-indol-3-yl)pyrrolidine-2,5-dione derivatives was synthesized and their biological activity was evaluated. The chemical structures of the newly prepared compounds were confirmed by 1H NMR, 13C NMR and ESI-HRMS spectra data. All tested compounds proved to be potent 5-HT1A receptor and serotonin transporter protein (SERT) ligands. Among them, compounds 15, 18, 19 and 30 showed significant affinity for 5-HT1A and SERT. Computer docking simulations carried out for compounds 15, 31 and 32 to models of 5-HT1A receptor and SERT confirm the results of biological tests. Due to high affinity for the 5-HT1A receptor and moderate affinity for SERT, compounds 31, 32, 35, and 37 were evaluated for their affinity for D2L, 5-HT6, 5-HT 7 and 5-HT2A receptors. In vivo tests, in turn, resulted in determining the functional activity of compounds 15, 18, 19 and 30 to the 5-HT1A receptor. The results of these tests indicate that all of the ligands possess properties characteristic of 5-HT1A receptor agonists.

N1-arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives are potent and selective 5-HT6 receptor antagonists

The development of a series of N1-sulfonyl-3-(1,2,3,6- tetrahydropyridin-4-yl)indole 5-HT6 antagonists is described. Two analogs, 15g and 15y, had 0.4 and 3.0 nM affinity, and antagonized the production of adenylate cyclase at sub-nanomolar concentrations. A series of N1-arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)indole derivatives was designed and synthesized. These compounds were shown to have high affinity for the 5-HT6 receptor. Two analogs, 4-[3-(1,2,3,6-tetrahydropyridin- 4-yl)-1H-indole-1-sulfonyl]-phenylamine 15g and 4-[3-(1,2,3,6-tetrahydropyridin- 4-yl)-5-methoxy-1H-indole-1-sulfonyl]-phenylamine 15y, had 0.4 and 3.0 nM affinity, respectively, and antagonized the production of adenylate cyclase at sub-nanomolar concentrations.

Compounds and methods

A method of treating a CCR5-mediated disease state in mammals which comprises administering to a mammal in need of such treatment, an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof.

3-(Tetrahydropyridinyl)indoles

Substituted indoles have been condensed with N-benzyl-4-piperidone to give 3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles. Under basic conditions, 5-, 6-, and 7- (but not 4-) substituted indoles give reasonable yields of the product. For condensation with 4-substituted indoles, acidic conditions and the presence of at least a 3-fold excess of N-benzyl-4-piperidone are beneficial. Under basic conditions, the condensation of indoles with N-substituted-3-piperidones is highly regioselective with the regioselectivity depending on the nature of the N-substituent. 4-Substituted indoles do not react with N-substituted-3-piperidones under basic conditions but give a single product under acidic conditions.