91430-80-7

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine is utilized as an intermediate in the production of agrochemicals. Its properties make it suitable for the creation of compounds that can be used in agricultural applications, such as pesticides and herbicides, to improve crop protection and yield.
Used in Organic Chemistry Research:
N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine is employed as a versatile building block in organic chemistry research. It is used to explore new chemical reactions and synthesize a wide range of chemical compounds, expanding the scope of chemical knowledge and innovation.
Used in Chemical Reaction Studies:
N,N-Dimethyl-3-(4-nitrophenoxy)-1-propanamine is also used in the study of chemical reactions, providing insights into reaction mechanisms and helping to develop new synthetic methods. Its reactivity and structural features make it a valuable tool for understanding and optimizing chemical processes in various applications.

InChI:InChI=1/C11H16N2O3/c1-12(2)8-3-9-16-11-6-4-10(5-7-11)13(14)15/h4-7H,3,8-9H2,1-2H3

Upstream product

• 79096-54-1 1-(3-Chloropropoxy)-4-nitrobenzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 3179-63-3 3-Dimethylamino-1-propanol 
• 350-46-9 4-Fluoronitrobenzene 
• 124-40-3 dimethyl amine 
• 100-02-7 4-nitro-phenol 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 1124-31-8 potassium 4-nitrophenolate 

Downstream Products

• 98596-65-7 Dimethyl-(4-nitro-benzyl)-[3-(4-nitro-phenoxy)-propyl]-ammonium; chloride 
• 98596-68-0 (4-Chloro-benzyl)-dimethyl-[3-(4-nitro-phenoxy)-propyl]-ammonium; chloride 
• 98596-52-2 (4-Bromo-benzyl)-dimethyl-[3-(4-nitro-phenoxy)-propyl]-ammonium; bromide 
• 128457-37-4 N-(6,11-dihydrodibenzothiepin-11-yl)-4-(3-dimethylaminopropoxy)aniline 
• 98740-92-2 Benzyl-dimethyl-[3-(4-nitro-phenoxy)-propyl]-ammonium; bromide 

Relevant academic research and scientific papers

With anti-tumor activity of a biphenyl amide compound and its preparation method and application

The invention discloses a biphenyl amide compound with antitumor activity as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, wherein in the structural formula, R1 is hydrogen or halogen; R2 is alkoxy with carbon number of 1-4; the terminal of R2 is replaced by tert-amido; R2 is linked to the para-position of amide via an oxygen atom. The compound has good tumor cell inhibiting activity in vitro and can be used for preparing antitumor drugs, especially anti-hepatoma drugs and anti-breast cancer drugs. The preparation method of the biphenyl amide compound, provided by the invention, has the advantages that the raw materials are accessible, the reaction conditions are mild, the reaction process is simple to operate, and the used reagent is cheap.

Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies

VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 μM and 5.98 μM, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors.

Design, synthesis and biological evaluation of pyridin-3-yl pyrimidines as potent Bcr-Abl inhibitors

A series of pyridin-3-yl pyrimidines was synthesized and evaluated for their Bcr-Abl inhibitory and anticancer activity. The preliminary results indicated that some compounds were promising anticancer agents. Compounds A2, A8, and A9 exhibited potent Bcr-Abl inhibitory activity, suggesting that aniline containing halogen substituents might be important for biological activity. Molecular docking was carried out to investigate the binding mode of them with Bcr-Abl. Details of synthesis and SAR studies of these compounds are described. A series of phenylaminopyrimidines was designed and synthesized as potent Bcr-Abl inhibitors. The screening of these rationally designed compounds for antitumor activity had identified three candidate leads which could be further optimized to improve the anticancer activities.

Design, synthesis and biological activities of Nilotinib derivates as antitumor agents

A novel class of Nilotinib derivatives, B1-B20, were synthesized in high yields using various substituted anilines. All the title compounds were evaluated for their inhibitory activities against Bcr-Abl and antiproliferative effects on human leukemia cell (K562). The pharmacological results indicated that some compounds exhibited promising anticancer activity. In particular, compound B14 containing tertiary amine side chain exhibited Bcr-Abl inhibitory activity similar to that of Nilotinib. It was suggested that the introduction of the tertiary amine moiety could improve Bcr-Abl inhibitory activity and antitumor effects.

INDOLINONE DERIVATIVES AND THEIR USE IN TREATING DISEASE-STATES SUCH AS CANCER

The present invention encompasses compounds of general formula (1) wherein R1 to R4 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.

Structure-based design of novel 2-amino-6-phenyl-pyrimido[5′, 4′:5,6]pyrimido[1,2-a]benzimidazol-5(6H)-ones as potent and orally active inhibitors of lymphocyte specific kinase (Lck): Synthesis, SAR, and in vivo anti-inflammatory activity

Lck, or lymphocyte specific kinase, is a cytoplasmic tyrosine kinase of the Src family expressed in T-cells and NK cells. Genetic evidence from knockout mice and human mutations demonstrates that Lck kinase activity is critical for T-cell receptor-mediated signaling, leading to normal T-cell development and activation. A small molecule inhibitor of Lck is expected to be useful in the treatment of T-cell-mediated autoimmune and inflammatory disorders and/or organ transplant rejection. In this paper, we describe the structure-guided design, synthesis, structure-activity relationships, and pharmacological characterization of 2-amino-6-phenylpyrimido[5′,4′:5,6]pyrimido[1,2- a]benzimidazol-5(6H)-ones, a new class of compounds that are potent inhibitors of Lck. The most promising compound of this series, 6-(2,6-dimethylphenyl)-2- ((4-(4-methyl-1-piperazinyl)phenyl)amino)pyrimido[5′,4′:5,6] pyrimido-[1,2-a]benzimidazol-5(6H)-one (25), exhibits potent inhibition of Lck kinase activity. This activity translates into inhibition of in vitro cell-based assays and in vivo models of T-cell activation and arthritis, respectively.

TRIAZOLOPYRIMIDINE DERIVATIVES

The invention relates to the discovery of triazolopyrimidine derivatives of formula (I), which have been found to exhibit inhibitory activity against the serine-tyrosine and tyrosine kinases.

Novel 2-aminopyrimidine carbamates as potent and orally active inhibitors of Lck: Synthesis, SAR, and in vivo antiinflammatory activity

The lymphocyte-specific kinase (Lck) is a cytoplasmic tyrosine kinase of the Src family expressed in T cells and NK cells. Genetic evidence in both mice and humans demonstrates that Lck kinase activity is critical for signaling mediated by the T cell receptor (TCR), which leads to normal T cell development and activation. A small molecule inhibitor of Lck is expected to be useful in the treatment of T cell-mediated autoimmune and inflammatory disorders and/or organ transplant rejection. In this paper, we describe the synthesis, structure-activity relationships, and pharmacological characterization of 2-aminopyrimidine carbamates, a new class of compounds with potent and selective inhibition of Lck. The most promising compound of this series, 2,6-dimethylphenyl 2-((3,5-bis(methyloxy)-4-((3-(4-methyl-1-piperazinyl)propyl)- oxy)phenyl)amino)-4-pyrimidinyl(2,4-bis(methyloxy)phenyl)carbamate (43) exhibits good activity when evaluated in in vitro assays and in an in vivo model of T cell activation.

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,