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

Description

4-(4-Methylpiperazino)aniline is an organic compound characterized by its purple solid appearance. It is a derivative of aniline, featuring a methylpiperazino group attached to the 4-position. 4-(4-Methylpiperazino)aniline is known for its role in the synthesis of various pharmaceutically relevant molecules.

Uses

Used in Pharmaceutical Industry:
4-(4-Methylpiperazino)aniline is used as a reagent for the preparation of benzyloxypyridinone derivatives, which possess c-Met kinase inhibitor properties. These derivatives are of significant interest in the pharmaceutical industry due to their potential applications in the development of targeted therapies for various diseases, including cancer.
The compound's role in the synthesis of c-Met kinase inhibitors highlights its importance in the development of novel treatments for conditions where c-Met kinase plays a crucial role in disease progression. By inhibiting this enzyme, these benzyloxypyridinone derivatives can potentially help in controlling the growth and spread of cancer cells, making 4-(4-Methylpiperazino)aniline a valuable component in the fight against cancer.

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

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

Downstream Products

• 76004-83-6 N⁴-(2-Diethylamino-ethyl)-N²-[4-(4-methyl-piperazin-1-yl)-phenyl]-quinazoline-2,4-diamine; hydrochloride 
• 211245-21-5 8-Isopropyl-2-[4-(4-methylpiperazin-1-yl)-phenylamino]-8H-pyrido[2,3-d]-pyrimidin-7-one 
• 289686-55-1 2,2-dimethyl-N-[4-(4-methyl-piperazin-1-yl)-phenyl]1-propionamide 
• 847950-09-8 6-(2,6-dimethylphenyl)-2-[4-(4-methylpiperazino)phenylamino]-benzo[4,5]-imidazolo[1,2-a]pyrimido[5,4-e]pyrimidin-5-one 
• 847950-62-3 6-(2,6-dimethylphenyl)-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)-8,9-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one 
• 870221-37-7 4-(2-chloropyridin-3-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine 
• 330550-98-6 N⁴-cyclopentyl-N²-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine 
• 357951-57-6 4-chloro-3-isopropyl-2-methylquinoline 
• 69875-49-6 4-chlro-3-cyanoquinoline 
• 80259-18-3 MMV006172 
• 915020-33-6 [4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester 

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.

Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer

NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.

NOVEL SULFONAMIDE DERIVATIVE WITH FUSED PYRIMIDINE SKELETON, HAVING EPIDERMAL GROWTH FACTOR RECEPTOR MUTATION INHIBITORY EFFECT

The present invention relates to a novel fused pyrimidine based sulfonamide derivative represented by Formula I, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same as an active ingredient. The novel fused pyrimidine based sulfonamide derivative of the present invention can effectively suppress the growth of cancer cells and resistance to drugs, which are induced by mutations in the tyrosine kinase domain of epidermal growth factor receptors, or the growth of cancer cells having such resistance.

FUSED PYRIMIDINE COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF

The present disclosure relates to a class of fused pyrimidine compounds of Formula I, their stereoisomers, tautomers, pharmaceutically acceptable salts, polymorphs, solvates, and hydrates thereof. The present disclosure also relates to a process of preparation of these fused pyrimidine compounds, and to pharmaceutical compositions containing them.