Intepirdine

Base Information

• Chemical Name: Intepirdine
• CAS No.: 607742-69-8
• Molecular Formula: C19H19N3O2S
• Molecular Weight: 353.445
• European Community (EC) Number: 629-854-8
• UNII: 2IOB2M82HY
• ChEMBL ID: CHEMBL1083390
• DSSTox Substance ID: DTXSID30976249
• Metabolomics Workbench ID: 153626
• NCI Thesaurus Code: C166572
• Nikkaji Number: J3.226.664I
• Pharos Ligand ID: 3Z4F9SYYGSU1
• Wikidata: Q855449
• Wikipedia: Intepirdine
• Mol file: 607742-69-8.mol

Synonyms:3-benzenesulfonyl-8-piperazin-1-ylquinoline;GSK-742457;intepirdine;RVT-101;SB 742457;SB-742457;SB742457

Chemical Property of Intepirdine

Chemical Property:

• Boiling Point: 608.3±45.0 °C(Predicted)
• PKA: 8?+-.0.10(Predicted)
• PSA: 70.68000
• Density: 1.292
• LogP: 3.95180
• Solubility.: insoluble in H2O; ≥17.65 mg/mL in DMSO; ≥2.13 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 353.11979803
• Heavy Atom Count: 25
• Complexity: 535

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-(Phenylsulfonyl)-8-(piperazin-1-yl)quinoline 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC=CC3=CC(=CN=C32)S(=O)(=O)C4=CC=CC=C4
• Recent ClinicalTrials: Study Evaluating Intepirdine (RVT-101) on Gait and Balance in Subjects With Dementia
• Recent EU Clinical Trials: A Long-Term Extension Study of the Safety and Tolerability of RVT-101 in Subjects with Dementia with Lewy Bodies (DLB)
• Description: SB-742457 is an orally bioavailable antagonist of the serotonin (5-HT) receptor subtype 5-HT6 (Ki = 1.4 nM). SB-742457 (1 μM) also binds to 5-HT1B, 5-HT2A, 5-HT2B, and 5-HT2C receptors with high affinity. SB-742457 reduces 5-HT6 activation of Gs-mediated cAMP production in a concentration-dependent manner with an EC50 value of 21 nM in NG108-15 neuroblastoma cells. In vivo, SB-742457 (1.5 mg/kg, p.o.) reverses deficits in novel object recognition induced by scopolamine in rats. It also reverses age-induced impairments in spatial memory acquisition and retention in rats in the Morris water maze. SB-742457 (3.0 mg/kg, i.p.) reduces the number of licking bouts by 24% compared with control in rats trained to lick a glucose solution, indicating a role in satiety and obesity management.
• Uses: SB 742457 is a selective 5-HT6 receptor antagonist which is known to be involved in improving cognitive function.

Technology Process of Intepirdine

There total 8 articles about Intepirdine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

piperazine (110-85-0) + 8-fluoro-3-(phenylsulfonyl)quinoline (866782-60-7) → 3-(phenylsulfonyl)-8-(piperazin-1-yl)quinoline (607742-69-8)

Guidance literature:

With potassium phosphate; In N,N-dimethyl-formamide; at 110 ℃; for 8h;

DOI:10.1021/acs.joc.8b00888

Reference yield: 75.0%

piperazine (110-85-0) + 8-iodo-3-(phenylsulfonyl)quinoline (607743-09-9) → 3-(phenylsulfonyl)-8-(piperazin-1-yl)quinoline (607742-69-8)

Guidance literature:

With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 40 ℃; for 16.5h;

Reference yield: 68.0%

piperazine (110-85-0) + 8-chloro-3-(phenylsulfonyl)quinoline (1429304-29-9) → 3-(phenylsulfonyl)-8-(piperazin-1-yl)quinoline (607742-69-8)

Guidance literature:

With palladium diacetate; sodium t-butanolate; ruphos; In 1,4-dioxane; at 90 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201305369

upstream raw materials:

piperazine

8-iodo-3-(phenylsulfonyl)quinoline

8-fluoro-3-(phenylsulfonyl)quinoline

8-chloro-3-(phenylsulfonyl)quinoline

Downstream raw materials:

8-{4-[(4-fluorophenyl)sulfonyl]piperazin-1-yl}-3-(phenylsulfonyl)quinoline

8-{4-[(2-fluorophenyl)sulfonyl]piperazin-1-yl}-3-(phenylsulfonyl)quinoline

(¹¹C)LuPET

Refernces

• 1、 Colomb, Julie,Becker, Guillaume,Fieux, Sylvain,Zimmer, Luc,Billard, Thierry. "Syntheses, radiolabelings, and in vitro evaluations of fluorinated pet radioligands of 5-HT6 serotoninergic receptors". . p. 3884 - 3890. Retrieved 2014/05/20.
• 2、 -. "NOVEL CHEMICAL PROCESS FOR THE SYNTHESIS OF QUINOLINE COMPOUNDS". Page/Page column 14-16. . Retrieved 2008/06/13.