149554-29-0

Basic information

• Product Name: 6-PIPERAZINONICOTINONITRILE
• Synonyms: BUTTPARK 37\12-47;2-(PIPERAZIN-1-YL)-5-PYRIDINECARBONITRILE;2-(1-PIPERAZINO)PYRIDINE-5-CARBONITRILE;6-PIERAZINONICOTINONITRILE;6-PIPERAZINONICOTINONITRILE;6-(PIPERAZINO)PYRIDINE-3-CARBONITRILE;6-Piperazinonicotinonitrile, tech;3-Pyridinecarbonitrile,6-(1-piperazinyl)-(9CI)
• CAS NO: 149554-29-0
• Molecular Formula: C₁₀H₁₂N₄
• Molecular Weight: 188.23
• Product Categories: PIPERIDINE;pharmacetical;Piperazines
• Mol File: 149554-29-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131 °C
• Boiling Point: 403.2 °C at 760 mmHg
• Flash Point: 197.6 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 1.04E-06mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.47±0.10(Predicted)
• CAS DataBase Reference: 6-PIPERAZINONICOTINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-PIPERAZINONICOTINONITRILE(149554-29-0)
• EPA Substance Registry System: 6-PIPERAZINONICOTINONITRILE(149554-29-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 20/21/22-36/37/38-25
• Safety Statements: 26-36/37/39-45-24/25-23
• RIDADR: 3439
• HazardClass: IRRITANT
• Hazardous Substances Data: 149554-29-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow powder or chunks

Uses

6-Piperazinonicotinonitrile acts as a reagent in the synthesis and molecular docking studies of piperazine-derived constrained inhibitors of DPP-IV for treatment of type 2 Diabetes.

InChI:InChI=1/C10H12N4/c11-7-9-1-2-10(13-8-9)14-5-3-12-4-6-14/h1-2,8,12H,3-6H2

Upstream product

• 683274-61-5 tert-butyl 4-(5-cyanopyridine-2-yl)piperazine-1-carboxylate 
• 33252-28-7 6-chloronicotinonitrile 
• 110-85-0 piperazine 

Downstream Products

• 683274-61-5 tert-butyl 4-(5-cyanopyridine-2-yl)piperazine-1-carboxylate 
• 1057679-83-0 N-{6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-ylmethyl}acetamide 
• 1057678-98-4 6-{4-[4-(3-trifluoromethyl-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinonitrile 
• 1027617-20-4 2-[5-(4-chlorophenyl)-1-(2-chlorophenyl)-3-[4-(5-cyanopyridin-2-yl)piperazine-1-carbonyl]-1H-pyrazol-4-yl]acetamide 
• 1057679-56-7 6-{4-[7-chloro-4-(4-fluorobenzyl)phthalazin-1-yl]piperazin-1-yl}nicotinonitrile 
• 1057679-59-0 6-{4-[6-chloro-4-(4-fluorobenzyl)phthalazin-1-yl]piperazin-1-yl}nicotinonitrile 
• 1057681-09-0 6-[4-(4-benzylisoquinolin-1-yl)piperazin-1-yl]nicotinonitrile 
• 1057679-63-6 1-[4-(5-cyanopyridin-2-yl)piperazin-1-yl]-4-(4-fluorobenzyl)phthalazine-6-carbonitrile 
• 1057679-61-4 4-[4-(5-cyanopyridin-2-yl)piperazin-1-yl]-1-(4-fluorobenzyl)phthalazine-6-carbonitrile 
• 1057681-34-1 4-{4-[4-(4-fluoro-benzyl)-5,6 7,8-tetrahydro-phthalzin-1-yl]-piperazin-1-yl}-nicotinonitrile 
• 1057681-13-6 4-{4-[6-(4-fluoro-benzyl)-5-methyl-pyridazin-3-yl]-piperazin-1-yl}-nicotinonitrile 
• 1057681-11-4 4-{4-[6-(4-fluoro-benzyl)-4-methyl-pyridazin-3-yl]-piperazin-1-yl}-nicotinonitrile 
• 1057681-00-1 6-[4-(1-benzylisoquinolin-4-yl)piperazin-1-yl]nicotinonitrile 

Relevant articles and documents

LipE guided discovery of isopropylphenyl pyridazines as pantothenate kinase modulators

Pantothenate kinase (PANK) is the critical regulator of intracellular levels of coenzyme A and has emerged as an attractive target for treating neurological and metabolic disorders. This report describes the optimization, synthesis, and full structure–activity relationships of a new chemical series of pantothenate competitive PANK inhibitors. Potent drug-like molecules were obtained by optimizing a high throughput screening hit, using lipophilic ligand efficiency (LipE) derived from human PANK3 IC50 values to guide ligand development. X-ray crystal structures of PANK3 with index inhibitors from the optimization were determined to rationalize the emerging structure activity relationships. The analysis revealed a key bidentate hydrogen bonding interaction between pyridazine and R306′ as a major contributor to the LipE gain observed in the optimization. A tractable series of PANK3 modulators with nanomolar potency, excellent LipE values, desirable physicochemical properties, and a well-defined structural binding mode was produced from this study.

Orally active 7-substituted (4-benzylphthalazin-1-yl)-2-methylpiperazin-1- yl]nicotinonitriles as active-site inhibitors of sphingosine 1-phosphate lyase for the treatment of multiple sclerosis

Sphingosine 1-phosphate (S1P) lyase has recently been implicated as a therapeutic target for the treatment of multiple sclerosis (MS), based on studies in a genetic mouse model. Potent active site directed inhibitors of the enzyme are not known so far. Here we describe the discovery of (4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]nicotinonitrile 5 in a high-throughput screen using a biochemical assay, and its further optimization. This class of compounds was found to inhibit catalytic activity of S1PL by binding to the active site of the enzyme, as seen in the cocrystal structure of derivative 31 with the homodimeric human S1P lyase. 31 induces profound reduction of peripheral T cell numbers after oral dosage and confers pronounced protection in a rat model of multiple sclerosis. In conclusion, this novel class of direct S1P lyase inhibitors provides excellent tools to further explore the therapeutic potential of T cell-targeted therapies in multiple sclerosis and other autoimmune and inflammatory diseases.

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