16153-81-4

Basic information

• Product Name: 4-(4-Methylpiperazino)aniline
• Synonyms: OTAVA-BB BB7110920492;AKOS BB-8657;AKOS B021941;4-(4-METHYLPIPERAZINO)ANILINE;4-(4-METHYLPIPERAZINE)ANILINE;4-(4-METHYLPIPERAZIN-1-YL)PHENYLAMINE;4-(4-METHYLPIPERAZIN-1-YL)ANILINE;1-(4-AMINOPHENYL)-4-METHYLPIPERAZINE
• CAS NO: 16153-81-4
• Molecular Formula: C₁₁H₁₇N₃
• Molecular Weight: 191.27
• Product Categories: PIPERIDINE;Amines and Anilines;Heterocycles;Amines;Phenyls & Phenyl-Het;Piperaizine;API intermediates;Piperazidine intermediates;Piperazines;Phenyls & Phenyl-Het
• Mol File: 16153-81-4.mol
• Article Data: 80

Chemical Properties

• Melting Point: 89 °C
• Boiling Point: 180°C/5mmHg(lit.)
• Flash Point: 164 °C
• Appearance: Kind of white to yellow powder
• Density: 1.092 g/cm³
• Vapor Pressure: 4.09E-05mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 8.08±0.42(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 4-(4-Methylpiperazino)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Methylpiperazino)aniline(16153-81-4)
• EPA Substance Registry System: 4-(4-Methylpiperazino)aniline(16153-81-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3259
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 16153-81-4(Hazardous Substances Data)

Usage

Chemical Properties

Purple solid

Uses

4-(4-Methylpiperazino)aniline is a reagent in the preparation of benzyloxypyridinone derivative which has c-Met kinase inhibitor properties.

InChI:InChI=1/C11H17N3/c1-13-6-8-14(9-7-13)11-4-2-10(12)3-5-11/h2-5H,6-9,12H2,1H3/p+1

Upstream product

• 109-01-3 1-methyl-piperazine 
• 586-78-7 para-nitrophenyl bromide 
• 106-39-8 bromochlorobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 260252-87-7 4-(4'-nitrophenyl)piperazine hydrochloride 
• 350-46-9 4-Fluoronitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 16155-03-6 1-methyl-4-(4-nitrophenyl)piperazine 

Downstream Products

• 837422-57-8 WH-4-023 
• 870221-37-7 4-(2-chloropyridin-3-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine 
• 357951-57-6 4-chloro-3-isopropyl-2-methylquinoline 
• 69875-49-6 4-chlro-3-cyanoquinoline 
• 80259-18-3 MMV006172 
• 640241-72-1 3-bromo-4-methoxy-N-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzamide 
• 936092-52-3 5-methyl-N₂-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidine-2,4-diamine 

Relevant articles and documents

New 2,6,9-trisubstituted purine derivatives as Bcr-Abl and Btk inhibitors and as promising agents against leukemia

Bcr-Abl and Btk kinases are among the targets that have been considered for the treatment of leukemia. Therefore, several strategies have focused on the use of inhibitors as chemotherapeutic tools to treat these types of leukemia, such as imatinib (for Bcr-Abl) or ibrutinib (for Btk). However, the efficacy of these drugs has been reduced due to resistance mechanisms, which have motivated the development of new and more effective compounds. In this study, we designed, synthesized and evaluated 2,6,9-trisubstituted purine derivatives as novel Bcr-Abl and Btk inhibitors. We identified 5c and 5d as potent inhibitors of both kinases (IC50 values of 40 nM and 0.58/0.66 μM for Abl and Btk, respectively). From docking and QSAR analyses, we concluded that fluorination of the arylpiperazine system is detrimental to the activity against two kinases, and we also validated our hypothesis that the substitution on the 6-phenylamino ring is important for the inhibition of both kinases. In addition, our studies indicated that most compounds could suppress the proliferation of leukemia and lymphoma cells (HL60, MV4-11, CEM, K562 and Ramos cells) at low micromolar concentrations in vitro. Finally, we preliminarily demonstrated that 5c inhibited the downstream signaling of both kinases in the respective cell models. Therefore, 5c or 5d possessed potency to be further optimized as anti-leukemia drugs by simultaneously inhibiting the Bcr-Abl and Btk kinases.

COMPOUNDS AND THEIR USES AS SPLEEN TYROSINE KINASE INHIBITORS

Provided are compounds of Formula (I) which can be used as Syk inhibitors and potently as therapeutic agents against diseases mediated by Syk.

FGFR Inhibitor compounds and uses thereof

The invention relates to FGFR inhibitor compounds and uses thereof. , The application discloses a compound as shown in a formula (I). A compound, or an optical isomer, a geometric isomer, a tautomer or isomer mixture thereof, or a pharmaceutically acceptable salt thereof, or a prodrug thereof, or a metabolite thereof. The application further relates to the application of the compound in medicine.

Discovery and in Vivo Anti-inflammatory Activity Evaluation of a Novel Non-peptidyl Non-covalent Cathepsin C Inhibitor

Cathepsin C (Cat C) participates in inflammation and immune regulation by affecting the activation of neutrophil serine proteases (NSPs). Therefore, cathepsin C is an attractive target for treatment of NSP-related inflammatory diseases. Here, the complete discovery process of the first potent "non-peptidyl non-covalent cathepsin C inhibitor"was described with hit finding, structure optimization, and lead discovery. Starting with hit 14, structure-based optimization and structure-activity relationship study were comprehensively carried out, and lead compound 54 was discovered as a potent drug-like cathepsin C inhibitor both in vivo and in vitro. Also, compound 54 (with cathepsin C Enz IC50 = 57.4 nM) exhibited effective anti-inflammatory activity in an animal model of chronic obstructive pulmonary disease. These results confirmed that the non-peptidyl and non-covalent derivative could be used as an effective cathepsin C inhibitor and encouraged us to continue further drug discovery on the basis of this finding.