105431-72-9

Basic information

• Product Name: 1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE
• Synonyms: LINOPIRDINE DIHYDROCHLORIDE;1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE;LINOPIRDINE (DUP996);Linopirdine2HCl;DuP 996, 1,3-Dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-2H-indol-2-one;1-Phenyl-3,3-bis(4-pyridinylmethyl)-2,3-dihydro-1H-indole-2-one;1-phenyl-3,3-bis(pyridin-4-ylmethyl)indolin-2-one;linopiridine
• CAS NO: 105431-72-9
• Molecular Formula: C₂₆H₂₁N₃O
• Molecular Weight: 391.47
• Product Categories: Potassium channel;Pharmaceuticals;DuP 996
• Mol File: 105431-72-9.mol

Chemical Properties

• Melting Point: 186-186.5 °C
• Boiling Point: 655.9 ºC at 760 mmHg
• Flash Point: 350.5 ºC
• Appearance: white to off-white/
• Density: 1.255 g/cm³
• Vapor Pressure: 4.45E-17mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: >10mg/mL
• PKA: 6.01±0.10(Predicted)
• CAS DataBase Reference: 1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE(105431-72-9)
• EPA Substance Registry System: 1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE(105431-72-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 105431-72-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE is used as a therapeutic agent for Alzheimer's disease treatment, acting as a cognition enhancer. It is believed to improve cognitive function by modulating neurotransmitter release and synaptic activity, which can be beneficial for patients suffering from cognitive decline associated with Alzheimer's disease.
Used in Research and Development:
In the field of research and development, 1,3-DIHYDRO-1-PHENYL-3,3-BIS(4-PYRIDINYLMETHYL)-2H-INDOL-2-ONE DIHYDROCHLORIDE can be utilized as a chemical probe or a lead compound for the development of new drugs targeting various neurological and cognitive disorders. Its unique structure and properties make it a valuable tool for understanding the underlying mechanisms of these conditions and for designing more effective treatments.

Biological Activity

Blocker of KCNQ voltage-gated potassium channels; blocks KCNQ2+3/M-currents (IC 50 = 4-7 μ M) and KCNQ1 homomeric channels (IC 50 = 8.9 μ M). Augments hippocampal ACh release and is a cognitive enhancer following oral administration in vivo .

InChI:InChI=1/C26H21N3O/c30-25-26(18-20-10-14-27-15-11-20,19-21-12-16-28-17-13-21)23-8-4-5-9-24(23)29(25)22-6-2-1-3-7-22/h1-17H,18-19H2

Upstream product

• 54751-01-8 4-(bromomethyl)pyridine 
• 30095-98-8 methyl (2-nitrophenyl)acetate 
• 98-80-6 phenylboronic acid 
• 154479-63-7 1,3-dihydro-3-(4-pyridinylmethylene)-1-phenyl-2H-indole-2-one 
• 149196-87-2 1,3-Dihydro-3-hydroxy-1-phenyl-3-(4-pyridinylmethyl)-2H-indol-2-one Acetate Ester 
• 105431-71-8 1,3-dihydro-3-hydroxy-1-phenyl-3-(pyridinylmethyl)-2H-indol-2-one 
• 154479-62-6 3-(4-pyridinylmethylene)-1-phenyl-2H-indolin-2-one 
• 122-39-4 diphenylamine 
• 75385-92-1 (N,N-diphenylcarbamoyl) formyl chloride 
• 723-89-7 1-phenyl-indole-2,3-dione 
• 3335-98-6 1-phenyl-1,3-dihydro-indol-2-one 
• 1822-51-1 4-picolylchloride hydrochloride 
• 105431-73-0 1,3-dihydro-1-phenyl-3-(4-pyridinylmethyl)-2H-indol-2-one 

Relevant articles and documents

Microwave-assisted rapid synthesis of neurotransmitter release enhancer linopiridine and its new analogues

A neurotransmitter release enhancer linopiridine and its new analogues have been synthesized rapidly in yields from the 1:2 coupling of oxiindole with 4-picolyl chloride hydrochloride on the surface of basic alumina doped with 37% KF under microwave irradiation in solvent-free conditions.

PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles

An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C?N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.

On the Mechanism of the Reduction of 1-Phenyl-3-(4-pyridinylmethylene)-2-oxindole with Sodium Borohydride in Methanol

Sodium borohydride reduction of 1-phenyl-3-(4-pyridinylmethylene)-2-oxindole 1 in methanol gives a high yield of the oxindole 2, a precursor to linopirdine.The reduction is accelerated by methanol and the major by-products during this reduction are the di

Method of treating neurological dysfunction using neutrotransmitter enhancers

This disclosure relates to a method of treating a neurological dysfunction in a mammal using a combination of at least one neurotransmitter enhancer and at least one serotonin receptor antagonist.

α,α-disubstituted aromatics and heteroaromatics as cognition enhancers

Cognitive defeciencies or neurological dysfunction in mammals are treated with α,α-disubstituted aromatic or heteroaromatic compounds. The compounds have the formula: STR1 or a salt thereof wherein X and Y are taken together to form a saturated or unsaturated carbocyclic or heterocyclic first ring and the shown carbon in said ring is α to at least one additional aromatic ring or heteroaromatic ring fused to the first ring; one of Het1 is 2, 3 or 4-pyridyl or 2, 4, or 5-pyrimidinyl and the other is selected from (a) 2, 3, or 4-pyridyl, (b) 2, 4, or 5-pyrimidinyl, (c) 2-pyrazinyl, (d) 3, or 4-pyridazinyl, (e) 3, or 4-pyrazolyl, (f) 2, or 3-tetrahydrofuranyl, and (g) 3-thienyl.

Process for preparing 3,3-disubstituted indolines

Processes for preparing 3,3-disubstituted indolines, particularly 3,3-dipyridine substituted indolines useful to treat cognitive or neurological dysfunction in a mammal, are provided.