178928-58-0

Basic information

• Product Name: Benzonitrile, 3-(1-piperazinyl)- (9CI)
• Synonyms: Benzonitrile, 3-(1-piperazinyl)- (9CI);3-PIPERAZIN-1-YLBENZONITRILE;1-(3-Cyanophenyl)piperazine ,97%;3-(1-Piperazinyl)benzonitrile
• CAS NO: 178928-58-0
• Molecular Formula: C₁₁H₁₃N₃
• Molecular Weight: 187.24102
• Product Categories: PIPERIDINE;pharmacetical
• Mol File: 178928-58-0.mol

Chemical Properties

• Boiling Point: 364.7 °C at 760 mmHg
• Flash Point: 174.3 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: Benzonitrile, 3-(1-piperazinyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 3-(1-piperazinyl)- (9CI)(178928-58-0)
• EPA Substance Registry System: Benzonitrile, 3-(1-piperazinyl)- (9CI)(178928-58-0)

Safety Data

• Hazardous Substances Data: 178928-58-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Benzonitrile, 3-(1-piperazinyl)(9CI) is used as a building block for the synthesis of various drug molecules in the pharmaceutical industry. Its unique structure and potential bioactive properties make it a valuable component in the development of new medications.
Used in Drug Synthesis:
Benzonitrile, 3-(1-piperazinyl)(9CI) is used as a key intermediate in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can contribute to the desired pharmacological properties of the final drug product.
Used in Medicinal Chemistry:
Benzonitrile, 3-(1-piperazinyl)(9CI) is utilized in medicinal chemistry for the design and optimization of drug candidates. Its incorporation into molecular structures can enhance the potency, selectivity, and pharmacokinetic properties of the resulting compounds.
Used in Drug Discovery:
Benzonitrile, 3-(1-piperazinyl)(9CI) is employed in drug discovery processes to identify novel therapeutic agents with potential applications in various disease areas. Its unique chemical properties and structural features make it a promising candidate for the development of innovative medications.

InChI:InChI=1/C11H13N3/c12-9-10-2-1-3-11(8-10)14-6-4-13-5-7-14/h1-3,8,13H,4-7H2

Upstream product

• 110-85-0 piperazine 
• 403-54-3 m-Fluorobenzonitrile 
• 69113-59-3 3-iodobenzonitrile 
• 6952-59-6 3-cyanobromobenzene 
• 2237-30-1 m-cyanoaniline 
• 67-68-5 dimethyl sulfoxide 
• 807624-20-0 1,1-dimethylethyl 4-(3-cyanophenyl)piperazine-1-carboxylate 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 898532-77-9 N-[4-[4-(3-cyanophenyl)piperazin-1-yl]butyl]benzo[b]furan-2-carboxamide 
• 898533-70-5 N-[4-[4-(3-cyanophenyl)piperazin-1-yl]butyl]3,4-dihydropyrazino[1,2-a]indol-1(2H)-one 
• 1373516-15-4 3-[4-(3-cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid 
• 1373516-13-2 3-[4-(3-cyano-phenyl)-piperazin-1ylmethyl]-benzoic acid methyl ester 

Relevant articles and documents

Synthesis and Pharmacological Characterization of Novel trans-Cyclopropylmethyl-Linked Bivalent Ligands That Exhibit Selectivity and Allosteric Pharmacology at the Dopamine D3 Receptor (D3R)

The development of bitopic ligands directed toward D2-like receptors has proven to be of particular interest to improve the selectivity and/or affinity of these ligands and as an approach to modulate and bias their efficacies. The structural similarities between dopamine D3 receptor (D3R)-selective molecules that display bitopic or allosteric pharmacology and those that are simply competitive antagonists are subtle and intriguing. Herein we synthesized a series of molecules in which the primary and secondary pharmacophores were derived from the D3R-selective antagonists SB269,652 (1) and SB277011A (2) whose structural similarity and pharmacological disparity provided the perfect templates for SAR investigation. Incorporating a trans-cyclopropylmethyl linker between pharmacophores and manipulating linker length resulted in the identification of two bivalent noncompetitive D3R-selective antagonists, 18a and 25a, which further delineates SAR associated with allosterism at D3R and provides leads toward novel drug development.

Guanidine derivative and application thereof

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A persistent latent reservoir of virus in CD4+ T cells is a major barrier to cure HIV. Activating viral transcription in latently infected cells using small molecules is one strategy being explored to eliminate latency. We previously described the use of a FlpIn.FM HEK293 cellular assay to identify and then optimize the 2-acylaminothiazole class to exhibit modest activation of HIV gene expression. Here, we implement two strategies to further improve the activation of viral gene expression and physicochemical properties of this class. Firstly, we explored rigidification of the central oxy-carbon linker with a variety of saturated heterocycles, and secondly, investigated bioisosteric replacement of the 2-acylaminothiazole moiety. The optimization process afforded lead compounds (74 and 91) from the 2-piperazinyl thiazolyl urea and the imidazopyridine class. The lead compounds from each class demonstrate potent activation of HIV gene expression in the FlpIn.FM HEK293 cellular assay (both with LTR EC50s of 80 nM) and in the Jurkat Latency 10.6 cell model (LTR EC50 220 and 320 nM respectively), but consequently activate gene expression non-specifically in the FlpIn.FM HEK293 cellular assay (CMV EC50 70 and 270 nM respectively) manifesting in cellular cytotoxicity. The lead compounds have potential for further development as novel latency reversing agents.

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.

Discovering Small-Molecule Estrogen Receptor α/Coactivator Binding Inhibitors: High-Throughput Screening, Ligand Development, and Models for Enhanced Potency

Small molecules, namely coactivator binding inhibitors (CBIs), that block estrogen signaling by directly inhibiting the interaction of the estrogen receptor (ER) with coactivator proteins act in a fundamentally different way to traditional antagonists, which displace the endogenous ligand estradiol. To complement our prior efforts at CBI discovery by denovo design, we used high-throughput screening (HTS) to identify CBIs of novel structure and subsequently investigated two HTS hits by analogue synthesis, finding many compounds with low micromolar potencies in cell-based reporter gene assays. We examined structure-activity trends in both series, using induced-fit computational docking to propose binding poses for these molecules in the coactivator binding groove. Analysis of the structure of the ER-steroid receptor coactivator (SRC) complex suggests that all four hydrophobic residues within the SRC nuclear receptor box sequence are important binding elements. Thus, insufficient water displacement upon binding of the smaller CBIs in the expansive complexation site may be limiting the potency of the compounds in these series, which suggests that higher potency CBIs might be found by screening compound libraries enriched with larger molecules.

ANTIVIRAL COMPOUNDS AND USE THEREOF

The invention relates to compounds, pharmaceutical compositions and methods useful for treating viral infection.

Novel Aryl Piperazine Derivatives With Medical Utility

This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D3, D2-like and 5-HT2 receptor subtypes, and in particular u

Parallel synthesis of N-arylpiperazines using polymer-assisted reactions

A series of N-arylpiperazines were prepared in a parallel fashion using palladium-catalyzed cross-coupling, or nucleophilic aromatic displacement chemistries, and polymer-assisted sequestration and purification techniques as key steps.

Pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists

Compounds having the structural formula I or a pharmaceutically acceptable salt thereof, wherein R is optionally substituted phenyl, furanyl, thienyl, pyridyl, pyridyl N-oxide, oxazolyl or pyrrolyl, or cycloalkenyl R1, R2, R3, R4 and R5 are H, alkyl or alkoxyalkyl; and Z is optionally substituted aryl or heteroaryl are disclosed. Also disclosed is the use of compounds of formula I in the treatment of central nervous system diseases, in particular Parkinson's disease, alone or in combination with other agents for treating Parkinson's disease, and pharmaceutical compositions comprising them.

Aryl-heteroaromatic products, compositions comprising them and use

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