78019-77-9

Usage

Uses

Used in Pharmaceutical Industry:
Piperidine, 4-methyl-1-(4-nitrophenyl)-, is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, such as analgesics, anti-inflammatory agents, and central nervous system (CNS) stimulants.
Used in Agrochemical Industry:
In the agrochemical industry, piperidine, 4-methyl-1-(4-nitrophenyl)-, is used as a building block for the synthesis of various agrochemicals, including insecticides, herbicides, and fungicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and diseases in agricultural settings.
Used in Organic Synthesis:
Piperidine, 4-methyl-1-(4-nitrophenyl)-, is used as a reagent in organic synthesis for the production of other organic compounds. Its versatile structure allows for various chemical reactions, enabling the synthesis of a wide range of organic molecules with different functional groups and properties.
Used in Material Science:
In the field of material science, piperidine, 4-methyl-1-(4-nitrophenyl)-, has potential applications as a precursor for the synthesis of polymers and other advanced materials. Its unique structure can contribute to the development of new materials with improved properties, such as enhanced mechanical strength, thermal stability, and chemical resistance.
Overall, piperidine, 4-methyl-1-(4-nitrophenyl)-, is a valuable chemical with diverse applications across various industries, including pharmaceuticals, agrochemicals, organic synthesis, and material science. Its unique structure and versatility make it an essential component in the development of new and innovative products.

InChI:InChI=1/C12H16N2O2/c1-10-6-8-13(9-7-10)11-2-4-12(5-3-11)14(15)16/h2-5,10H,6-9H2,1H3

Upstream product

• 626-58-4 4-methylpiperidin 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 1423290-73-6 C₂₈H₃₃N₇ 
• 1414781-23-9 C₂₁H₃₀N₆ 
• 1414781-19-3 N⁴-cyclopentyl-N²-(4-(4-methylpiperidin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine 
• 342013-25-6 4-(4-methylpiperidin-1-yl)aniline 
• 78020-03-8 4-methyl-1-(4-nitrophenoxy)-piperidine 
• 78019-93-9 4-methyl-1-(4-nitrophenyl)-piperidine N-oxide 

Relevant academic research and scientific papers

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.

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

Heterocyclic compounds as CDK4 or CDK6 or other CDK inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy

AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Heterocyclic compounds as Wee1 inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Design, synthesis and biological evaluation of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivative as potent antitumor agents

To develop novel therapeutic agents with anticancer activities, two series of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivatives were designed and synthesized. All compounds were tested for anti-proliferative activities against five cancer cell lines. The structure-activity relationships (SARs) studies were conducted through the variation in two regions, the moiety of A ring and the terminal aniline B on pteridinone core. 1-Methyl-1,2,4-triazole derivative L7 with 2,6-dimethylpiperazine showed the most potent antiproliferative activity against A549, PC-3, HCT116, MCF-7 and MDA-MB-231 cell lines with IC50 values of 0.16 μM, 0.30 μM, 0.51 μM, 0.30 μM, and 0.70 μM, respectively. Combined with the results of the molecular docking and enzymatic studies, the PLK1 was very likely to be one of the drug targets of compound L7. Furthermore, to clarify the anticancer mechanism of compound L7, further explorations in the bioactivity were conducted. The results showed that compound L7 obviously inhibited proliferation of A549 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells, and arrested G1 phase of A549 cells.

Design, synthesis and biological evaluation of novel 2,4-diaminopyrimidine derivatives as potent antitumor agents

For developing novel therapeutic agents with anticancer activities, two series of novel 2,4-diaminopyrimidine derivatives possessing triazolopiperazine or 1,4,8-triazaspiro[4.5]decan-3-one scaffolds were designed and synthesized. Preliminary investigations showed that some compounds exhibited moderate to excellent potency against four tested cancer cell lines as compared with palbociclib and momelotinib. In particular, the most promising compounds 9k and 13f showed the most potent antitumor activities with IC50 values of 2.14/1.98 μM, 3.59/2.78 μM, 5.52/4.27 μM, and 3.69/4.01 μM against A549, HCT-116, PC-3 and MCF-7 cell lines, respectively. Structure-activity relationship (SAR) studies were conducted based on the variation of the moiety of the aromatic ring and the terminal aniline on the pyrimidine core. Furthermore, the mechanism of their anticancer activity was clarified by further exploring the bioactivity. The results showed that compound 9k obviously inhibited the proliferation of A549 cell lines, induced a great decrease in the mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells and prolonged the A549 cell cycle distribution, representing blockage at the G2-M phase and accumulation at the S phase.

Discovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3

Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives. All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the “A” phenyl ring and “B” phenyl ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC50 = 27 nM, FLT3 IC50 = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G1/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor.

Diamine monomer with triphenylamine structure containing p-substituted cyclic amine, preparation method and application of diamine monomer

The invention provides a diamine monomer with a triphenylamine structure containing p-substituted cyclic amine, a preparation method and application of the diamine monomer in preparing polyamide, and belongs to the technical field of organic compound preparation. The synthetic method comprises the following four steps: performing a nucleophilic substitution reaction on a cyclic amine compound and p-fluoronitrobenzene under the action of potassium carbonate to obtain a mononitrate compound containing a cyclic amine structure; then, taking Pd/C as a catalyst and hydrazine hydrate as a reducing agent to obtain a monoamino compound containing a cyclic amine structure; then, performing a nucleophilic substitution reaction on the monoamino compound and p-fluoronitrobenzene under the action of cesium fluoride to obtain a dinitro monomer with a triphenylamine structure containing p-substituted cyclic amine; finally, taking Pd/C as a catalyst and hydrazine hydrate as a reducing agent to obtain the diamine monomer with the triphenylamine structure containing p-substituted cyclic amine. The diamine monomer can react with various diacid to prepare the polyamide with the electrochromic performance.

Structural optimization and structure-activity relationships of N 2-(4-(4-methylpiperazin-1-yl)phenyl)- N 8-phenyl-9 H -purine-2,8-diamine derivatives, a new class of reversible kinase inhibitors targeting both EGFR-activating and resistance mutations

This paper describe the structural optimization of a hit compound, N 2-(4-(4-methylpiperazin-1-yl)phenyl)-N8-phenyl-9H-purine- 2,8-diamine (1), which is a reversible kinase inhibitor targeting both EGFR-activating and drug-resistance (T790M) mutations but has poor binding affinity. Structure-activity relationship studies led to the identification of 9-cyclopentyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-N 8-phenyl-9H-purine-2,8-diamine (9e) that exhibits significant in vitro antitumor potency against the non-small-cell lung cancer (NSCLC) cell lines HCC827 and H1975, which harbor EGFR-activating and drug-resistance mutations, respectively. Compound 9e was further assessed for potency and selectivity in enzymatic assays and in vivo anti-NSCLC studies. The results indicated that compound 9e is a highly potent kinase inhibitor against both EGFR-activating and resistance mutations and has good kinase spectrum selectivity across the kinome. In vivo, oral administration of compound 9e at a dose of 5 mg/kg caused rapid and complete tumor regression in a HCC827 xenograft model, and an oral dose of 50 mg/kg initiated a considerable antitumor effect in an H1975 xenograft model.

Aminoalkyl-substituted aromatic bicyclic compounds, methods for their preparation and their use as pharmaceuticals

The present invention relates to aminoalkyl-substituted aromatic bicyclic compounds of formula I, which are valuable pharmaceutically active compounds that are suitable, for example, for the treatment of obesity, type II diabetes, arteriosclerosis, high blood pressure, paresthesia, depression, anxiety, anxiety neuroses, schizophrenia, disorders associated with the circadian rhythm, and drug abuse, as well as normalizing lipid metabolism.