180161-14-2

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a key intermediate in the synthesis of new drug candidates due to its potential biological activity and unique structural features.
Used in Anticancer Drug Development:
In the pharmaceutical industry, 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a precursor for the development of novel anticancer drugs, leveraging its potential to target and inhibit specific cancer-related pathways.
Used in Antimicrobial Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is utilized as a component in the creation of new antimicrobial agents, capitalizing on its ability to combat resistant microbial strains.
Used in Neurological Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is employed as a building block for the development of neurological drugs, aiming to address various neurological disorders and conditions by modulating specific neurotransmitter systems or receptors.
Used in Biological Research:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a chemical tool in biological research to probe and understand complex biological systems, offering insights into the mechanisms of disease and potential therapeutic targets.
The diverse potential applications of 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE make it a compound of significant interest to researchers in the pharmaceutical and biomedical fields, as it holds promise for advancing the development of innovative treatments and diagnostic tools.

Upstream product

• 399-51-9 6-fluoro-1H-indole 
• 41979-39-9 4-piperidone hydrochloride 
• 41661-47-6 piperidin-4-one 
• 255724-71-1 5-fluoro-2-iodoaniline 
• 255724-68-6 2-ethynyl-5-fluoroaniline 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 

Downstream Products

• 76315-55-4 6-fluoro-3-(piperidin-4-yl)-1H-indole 
• 180160-70-7 7-chloro-3-(piperidin-4-yl)-1H-indole 
• 223521-24-2 N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)eth-1-yl)-3-(4-(6-fluoroindol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl)propanamide 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of novel histamine H 1 antagonists: Indolylpiperidinyl benzoic acid derivatives

A series of indolylpiperidinyl derivatives were prepared and evaluated for their activity as histamine H1 antagonists. Structure-activity relationship studies were directed toward improving in vivo activity and pharmacokinetic profile of our first lead (1). Substitution of fluorine in position 6 on the indolyl ring led to higher in vivo activity in the inhibition of histamine-induced cutaneous vascular permeability assay but lower selectivity toward 5HT2 receptor. Extensive optimization was carried out within this series and a number of histamine H1 antagonists showing potency and long duration of action in vivo and low brain penetration or cardiotoxic potential were identified. Within this novel series, indolylpiperidines 15, 20, 48, 51 and 52 exhibited a long half-life in rat and have been selected for further preclinical evaluation.

Studies toward the discovery of the next generation of antidepressants. Part 2: Incorporating a 5-HT1A antagonist component into a class of serotonin reuptake inhibitors

The design and synthesis of a novel series of indole derivatives (9) having dual 5-HT transporter reuptake and 5-HT1A antagonist activity are described.

PHARMACEUTICAL COMPOUNDS

A pharmaceutical compound of the formula in which R1 is hydrogen, C1-4 alkyl, C1-4 alkoxy or halo, and R2 is hydrogen, C1-4 alkyl or C1-4 alkoxy; or a salt thereof.

3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists

The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.

Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction

A rearrangement reaction involving the indole nucleus was investigated using stereochemical markers and low-temperature NMR experiments. Treatment of(3S,4S)-3-hydroxy-4-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with diethylaminosulfur trifluoride gave stereospecifically (3S,4S)-4-fluoro-3-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with complete regioselectivity. The initial formation of a reactive spirocyclopropyl-3H-indole intermediate is believed to be responsible for the stereo- and regiochemical outcome of the reaction.

Benzothiadiazinyl-indole derivatives and their use as serotonin receptor ligands

Compounds having the formula: in which n is 1 or 2, m is 1 or 2, p is 1 to 6, q is 0 or 1 to 3, R1and R2are each hydrogen or C1-4alkyl, R3, R4and R5are each hydrogen, C1-4alkyl, optionally substituted phenyl or optionally substituted phenyl-C1-4alkyl, or R3and R4together form an alkylene link of formula -(CH2)3- or -(CH2)4-, or R4and R5together with the carbon atom to which they are attached form a C3-6cycloalkyl group, R6is C1-4alkyl, C1-4alkoxy, carboxy, hydroxy, cyano, halo, trifluoromethyl, nitro or amino, the dotted line represents an optional double bond, and the fluorine atom is attached at the 6 or 7-position; and salts and esters thereof, are binding to the 5-HT serotonin receptor and are useful in the treatment of CNS disorders.

1H-2,1,3-benzothiadiazine-2,2-dioxide compounds or derivatives thereof

A pharmaceutical compound having the formula: STR1 in which n is 1 or 2, m is 1 or 2, p is 1 to 6, q is 0 or 1 to 3, R1 and R2 are each hydrogen or C1-4 alkyl, R3, R4 and R5 are each hydrogen, C1-4 alkyl, optionally substituted phenyl or optionally substituted phenyl-C1-4 alkyl, or R3 and R4 together form an alkylene link of formula --(CH2)3 -- or --(CH2)4 --, or R4 and R5 together with the carbon atom to which they are attached form a C3-6 cycloalkyl group, R6 is C1-4 alkyl, C1-4 alkoxy, carboxy, hydroxy, cyano, halo, trifluoromethyl, nitro or amino, the dotted line represents an optional double bond, and the fluorine atom is attached at the 6 or 7-position; and salts and esters thereof.

1H-indole and benzo(b)thiophene derivatives with 4-(1,2,3,6-tetra:hydro:pyridinyl)- and 4-piperidinyl-groups bound to the heterocyclic ring as inhibitors of serotonin reuptake

The pharmaceutical use of novel compounds of formula I: where Z is a structure of formula A-B is -C=CH- or -C(R5)-CH2-; X is S or NR4; R1is H, halo, formyl, C1-C4alkyl, C1-C4alkoxy, thienylmethyloxy, 4,5-dihydrothiazol-2-yl, cyano, nitro, carboxamido, trifluoromethyl or hydroxy; R2is H or halo; R3is H, C1-C4alkyl, (C1-C4alkylene)-aryl, or -CH2-Y-NR7R8; R4is H, C1-C4alkyl, C1-C5acyl, or phenylsulfonyl; R5is H or OH; R6is H or methyl; Y is -CH2- or -C(O)-; R7is pyridinyl; and R8is H or -C(O)-(C3-C6cycloalkyl); and pharmaceutically acceptable salts thereof.