102392-05-2

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-
• Synonyms: 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-;N-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-phthaliMide;2-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)isoindoline-1,3-dione;2-{4-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-butyl}-isoindole-1,3-dione
• CAS NO: 102392-05-2
• Molecular Formula: C₂₃H₂₇N₃O₃
• Molecular Weight: 393.47878
• Mol File: 102392-05-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-(102392-05-2)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-(102392-05-2)

Safety Data

• Hazardous Substances Data: 102392-05-2(Hazardous Substances Data)

Usage

Molecular structure

The compound is a derivative of isoindole-1,3(2H)-dione with a piperazine group and a 2-methoxyphenyl group attached to it.

Pharmaceutical use

The compound is commonly used as a pharmaceutical ingredient due to its potential medical applications.

Potential therapeutic applications

It has been studied for its potential use in the treatment of various medical conditions, including mental health and neurological disorders.

Drug development

The compound may also have applications in the development of new drugs for other therapeutic areas.

Complex structure

The compound has a complex structure which makes it a valuable target for further research and development in the pharmaceutical industry.

Upstream product

• 136918-14-4 phthalimide 
• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 1074-82-4 potassium phtalimide 
• 5464-78-8 1-(2-methoxyphenyl)piperazine hydrochloride 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 

Downstream Products

• 1257244-86-2 sodium N-{4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl}dithiocarbamate 

Relevant articles and documents

Synthesis, preclinical evaluation and molecular modelling of macrocyclic appended 1-(2-methoxyphenyl)piperazine for 5-HT1A neuroreceptor imaging

5-HT1A receptors are known to be implicit in a number of neuropsychiatric fluctuations related to mood and anxiety. Their visualization in the human brain using PET, SPECT or MRI is of great importance in the management and treatment of neurolo

High Affinity Dopamine D3 Receptor (D3R)-Selective Antagonists Attenuate Heroin Self-Administration in Wild-Type but not D3R Knockout Mice

The dopamine D3 receptor (D3R) is a promising target for the development of pharmacotherapeutics to treat substance use disorders. Several D3R-selective antagonists are effective in animal models of drug abuse, especially

Synthesis and radiolabelling of [123I]-4-iodo-N-(4-(4-(2-methoxyphenyl)-piperazin-1-yl) butyl)-benzamide, a potential dopamine D3 antagonist for SPECT studies

Schizophrenia is a devastating mental disorder characterized by relapsing psychotic episodes accompanied with emotional, professional and social decline. The classical dopamine hypothesis of schizophrenia postulates that hyperactivity of dopaminergic neur

Synthesis and radiolabelling of [123I]-4-iodo-N-(4-(4-(2-methoxyphenyl)-piperazin-1-yl) butyl)-benzamide, a potential dopamine D3 antagonist for SPECT studies

Schizophrenia is a devastating mental disorder characterized by relapsing psychotic episodes accompanied with emotional, professional and social decline. The classical dopamine hypothesis of schizophrenia postulates that hyperactivity of dopaminergic neur

Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides

We describe the incorporation of the well-investigated class of photochromic dithienylethenes (DTEs) and fulgides into known dopamine receptor ligands such as 1,4-disubstituted aromatic and hydroxybenzoxazinone piperazines as well as aminoindanes. Subtype

Design and synthesis of new potent 5-HT7 receptor ligands as a candidate for the treatment of central nervous system diseases

Owing to their multifunctional pharmacological profiles (including dual 5-HT1A/5-HT7 action), arylpiperazine derivatives are widely used for treating central nervous system diseases including the depression or neuropathic pain. Herein we describe the design, synthesis and evaluation of biological activity of novel 5-HT7 ligands derived of 2,4,6-triamino-1,3,5-triazine. The studied compounds showed affinity and high selectively towards 5-HT7 receptor with the two most active compounds 34 (Ki = 61 nM), 22 (Ki = 109 nM) showing good metabolic stability and moderate affinity to CYP3A4 isoenzyme. Compound 22 had high hepatotoxicity at a concentration below 50 μM, while compound 34 showed low hepatotoxicity even at a concentration above 50 μM.

Synthesis, in silico, and in vitro studies of novel dopamine D2 and D3 receptor ligands

Dopamine is an important neurotransmitter in the human brain and its altered concentrations can lead to various neurological diseases. We studied the binding of novel compounds at the dopamine D2 (D2R) and D3 (D3/sub

The one-pot synthesis of butyl-1H-indol-3-alkylcarboxylic acid derivatives in ionic liquid as potent dual-acting agent for management of BPH

Based on the SAR of both α1-AR antagonists and 5α-reductase (5AR) inhibitors, the dual-acting agent 4-(1-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)-1H-indol-3-yl)butanoic acid 4aaa was designed against BPH and synthesized by two steps of N-alkylation. One-pot protocol towards 4aaa was newly developed. With IL [C6min]Br as solvent, the yield of 4aaa was increased to 75.1% from 16.0% and the reaction time was shortened in 1.5 h from 48 h. 25 derivatives structurally based on arylpiperazine and indolyl butyric acid with alkyl linker were prepared. The protocol was futher extended to get another 14 derivatives wherein O-alkylation was involved, and applied to the synthesis of biologically efficient molecules DPQ and Aripiprazole. Expectedly, compound 4aaa exhibited dual inhibition of α1-AR and 5α-reductase, and exhibited no obvious cytotoxicity against human cells. The pharmacokinetic properties of 4aaa was also determined.

Design, synthesis, and evaluation of N-(4-(4-phenyl piperazin-1-yl)butyl)-4-(thiophen-3-yl)benzamides as selective dopamine D3 receptor ligands

As part of our on-going effort to explore the role of dopamine receptors in drug addiction and identify potential novel therapies for this condition, we have a identified a series of N-(4-(4-phenyl piperazin-1-yl)butyl)-4-(thiophen-3-yl)benzamide D3 ligands. Members of this class are highly selective for D3 versus D2, and we have identified two compounds (13g and 13r) whose rat in vivo IV pharmacokinetic properties that indicate that they are suitable for assessment in in vivo efficacy models of substance use disorders.

Benzyl Phenylsemicarbazides: A Chemistry-Driven Approach Leading to G Protein-Biased Dopamine D4 Receptor Agonists with High Subtype Selectivity

Many subtype-selective dopamine receptor ligands developed for the D2-D4 family incorporate a 1-arylpiperazine-derived primary recognition motif, which is connected to a lipophilic moiety occupying an extended binding pocket (EBP) of the receptor via an aliphatic linker of variable lengths. The evaluation of a novel group of dopamine receptor ligands now showed that highly subtype-selective ligands [up to Ki(D4.4) = 0.25 nM, D2L/D4.4 = 320, D3/D4.4 = 710 for APH199 (17)] can be obtained by choosing a relatively large and conformationally flexible 1-benzyl-1-phenylsemicarbazide substructure to fill the EBP. The novel chemotype APH199 (17) was found to act as a full agonist at the D4 receptor showing significant bias toward G protein activation over β-arrestin recruitment in comparison to quinpirole.