16154-72-6

Basic information

• Product Name: 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE
• Synonyms: 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE;3-CHLORO-4-(4-METHYL-PIPERAZIN-1-YL)-PHENYLAMINE;AKOS BB-7856;AKOS B033196;1-(4-AMINO-2-CHLOROPHENYL)-4-METHYLPIPERAZINE;ASISCHEM Z03257;TIMTEC-BB SBB011555;BENZENAMINE, 3-CHLORO-4-(4-METHYL-PIPERAZINYL)
• CAS NO: 16154-72-6
• Molecular Formula: C₁₁H₁₆ClN₃
• Molecular Weight: 225.72
• Product Categories: Miscellaneous
• Mol File: 16154-72-6.mol

Chemical Properties

• Melting Point: 141 °C
• Boiling Point: 382.135 °C at 760 mmHg
• Flash Point: 184.909 °C
• Appearance: Kind of white to yellow powder
• Density: 1.207 g/cm³
• Vapor Pressure: 4.83E-06mmHg at 25°C
• Refractive Index: 1.598
• PKA: 7.54±0.42(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE(16154-72-6)
• EPA Substance Registry System: 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE(16154-72-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 16154-72-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE is used as a pharmaceutical intermediate for the synthesis of various drugs, including antipsychotics and antidepressants. Its structural features facilitate the development of medications that can target specific biological pathways, contributing to the treatment of mental health disorders.
Used in Research Chemicals:
In the field of research, 3-CHLORO-4-(4-METHYLPIPERAZIN-1-YL)ANILINE serves as a crucial component in the development of new organic compounds. Its potential interactions with biological systems make it a valuable tool for exploring and understanding the mechanisms of action in medicinal chemistry, furthering scientific knowledge and innovation in drug discovery.

InChI:InChI=1/C11H16ClN3/c1-14-4-6-15(7-5-14)11-3-2-9(13)8-10(11)12/h2-3,8H,4-7,13H2,1H3

Upstream product

• 16153-81-4 4-(4-Methyl-piperazino)-anilin 
• 915020-33-6 [4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 109-01-3 1-methyl-piperazine 
• 16154-62-4 1-(2-chloro-4-nitro-phenyl)-4-methyl-piperazine 
• 915020-32-5 [3-chloro-4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester 

Downstream Products

• 1372529-53-7 N₂-(3-chloro-4-(4-methylpiperazin-1-yl)phenyl)-N₄-cyclopropylfuro[3,2-d]pyrimidine-2,4-diamine 
• 1232814-54-8 C₂₃H₂₄ClN₇O 

Relevant articles and documents

PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER

The invention provides compounds of the formula (1): or a salt or tautomer thereof wherein A, R1, R2, R3, R4, R5 and R6 are as defined herein. The compounds are inhibitors of Wee1 and/or PLK1 kinase and are envisaged to be useful in the treatment of cancers.

The synthesis and bioactivity of pyrrolo[2,3-d]pyrimidine derivatives as tyrosine kinase inhibitors for NSCLC cells with EGFR mutations

EGFR mutations are an ongoing challenge in the treatment of NSCLC, and demand continuous updating of EGFR TKI drug candidates. Pyrrolopyrimidines are one group of versatile scaffolds suitable for tailored drug development. However not many precedents of this type of pharmacophore have been investigated in the realm of third generation of covalent EGFR-TKIs. Herein, a series of pyrrolo[2,3-d]pyrimidine derivatives able to block mutant EGFR activity in a covalent manner were synthesized, through optimized Buchwald-Hartwig C–N cross coupling reactions. Their preliminary bioactivity and corresponding inhibitory mechanistic pathways were investigated at molecular and cellular levels. Several compounds exhibited increased biological activity and enhanced selectivity compared to the control compound. Notably, compound 12i selectively inhibits HCC827 cells harboring the EGFR activating mutation with up to 493-fold increased efficacy compared to in normal HBE cells. Augmented selectivity was also confirmed by kinase enzymatic assay, with the test compound selectively inhibiting the T790 M activating mutant EGFRs (IC50 values of 0.21 nM) with up to 104-fold potency compared to the wild-type EGFR (IC50 values of 22 nM). Theoretical simulations provide structural evidence of selective kinase inhibitory activity. Thus, this series of pyrrolo[2,3-d]pyrimidine derivatives could serve as a starting point for the development of new EGFR-TKIs.

WEE1 inhibitors as well as preparation and application thereof

The invention relates to WEE1 inhibitors as well as preparation and application thereof. The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, and their use in the preparation of medicaments for the treatment of diseases associated with WEE1 activity.

BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BDR4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BDR4 are also disclosed. In certain aspects, disclosed are compounds of Formula I through IV.

POTENT DUAL BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BRD4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BRD4 are also disclosed. In certain aspects, disclosed are compounds of Formula I-IV.

PYRAZOLYL-PYRIMIDINES AS KINASE INHIBITORS

Disclosed are compounds having the formula (I): wherein Z, n, R1, R1A, R3, R4, and R5 are as defined herein, and methods of making and using the same.

N-(3,4-disubstituted phenyl) salicylamide derivatives

A compound represented by the following formula (I) or a salt thereof: wherein R1, R2, R3 and R4 represent hydrogen atom, a halogen atom, cyano group, nitro group, a C1-4 alkyl group, a halogenated C

IMIDAZOQUINOLINES AS LIPID KINASE INHIBITORS

The invention relates to novel organic compounds of formula (I) processes for the preparation thereof, the application thereof in a process for the treatment of the human or animal body, the use thereof - alone or in combination with one or more other pharmaceutically active compounds - for the treatment of an inflammatory or obstructive airway disease, such as asthma, disorders commonly occurring in connection with transplantation, or a proliferative disease, such as a tumor disease.

2-AMINO-4-HYDROXY-5-PYRIMIDINECARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF T CELL ACTIVATION FOR THE TREATMENT OF INFLAMMATORY DISEASES

The present invention relates to pyrimidine or pyridine carboxamides or pharmaceutically-acceptable salts thereof. Also included is a method of treatment of inflammation, inhibition of T cell activation and proliferation, arthritis, rheumatoid arthritis,

2-AMINOPYRIMIDINE AND 2-AMINOPYRIDINE-4-CARBAMATES FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASES

The present invention relates to pyrimidine or pyridine carbamate compounds having the general Formula (1) and pharmaceutically acceptable salts or derivatives thereof. Also included are methods of treatment of various diseases and conditions, including inflammation, inhibition of T cell activation and proliferation, arthritis, organ transplant, ischemic or reperfusion injury, myocardial infarction, stroke, multiple sclerosis, inflammatory bowel disease, Crohn's disease, lupus, hypersensitivity, type 1 diabetes, psoriasis, dermatitis, Hashimoto's thyroiditis, Sjogren's syndrome, autoimmune hyperthyroidism, Addison's disease, autoimmune diseases, glomerulonephritis, allergic diseases, asthma, hayfever, eczema, cancer, colon carcinoma, thymoma, just to name a few, in a mammal, the methods comprising administering a therapeutically-effective amount a compound of Formula I, or a salt or derivative form thereof, as described above.