92033-76-6

Usage

Uses

Used in Medicinal Chemistry:
1-(2-(4-Nitrophenoxy)ethyl)piperidine is utilized as a key intermediate in the synthesis of pharmaceuticals for its piperidine scaffold, which is a common structural element in many bioactive compounds. Its presence in drug molecules can influence their pharmacokinetic and pharmacodynamic properties, enhancing their therapeutic potential.
Used in Drug Development:
In the pharmaceutical industry, 1-(2-(4-Nitrophenoxy)ethyl)piperidine is employed as a building block for the development of new drugs. Its unique structural features allow for the creation of molecules with specific biological activities, targeting a range of therapeutic areas.
Used in Chemical Research:
1-(2-(4-Nitrophenoxy)ethyl)piperidine serves as a subject of study in chemical research, where its properties and reactivity are explored. This research can lead to a better understanding of its behavior in various chemical reactions and its potential use in the synthesis of complex organic compounds.
Used in Environmental and Toxicological Studies:
Given the need to assess the safety and environmental impact of new chemical entities, 1-(2-(4-Nitrophenoxy)ethyl)piperidine is used in toxicological studies to determine its effects on living organisms and the environment. This ensures that any potential risks associated with its use are identified and mitigated.

Upstream product

• 100-02-7 4-nitro-phenol 
• 110-89-4 piperidine 
• 3383-72-0 1-(2-chloroethoxy)-4-nitrobenzene 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 3040-44-6 1-piperidinoethanol 
• 350-46-9 4-Fluoronitrobenzene 
• 2008-75-5 N-chloroethylpiperidine hydrochloride 
• 13288-06-7 1-(2-bromoethoxy)-4-nitrobenzene 
• 1932-03-2 2-(piperidin-4-yl)ethyl chloride 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 

Downstream Products

• 616882-52-1 1-[2-(4-nitro-3-trimethylsilanylmethyl-phenoxy)-ethyl]-piperidine 
• 1567327-14-3 2-(4-(2-(piperidin-1-yl)ethoxy)phenyl)benzo[d][1,2]selenazol-3(2H)-one 
• 1567327-21-2 5,6-dimethoxy-2-(4-(2-(piperidin-1-yl)ethoxy)phenyl)benzo[d][1,2]selenazol-3(2H)-one 
• 1430234-73-3 C₃₀H₃₂N₆O₃ 
• 92326-19-7 1,4-Di(N,N-pentamethylen)-piperazinium-dibromid 
• 38948-27-5 4-(2-(piperidin-1-yl)ethoxy)aniline 
• 616882-63-4 1-(2-methoxy-quinolin-3-yl)-2-[2-nitro-5-(2-piperidin-1-yl-ethoxy)-phenyl]-ethanol 
• 616882-51-0 2-methoxy-3-{2-[2-nitro-5-(piperidin-1-yl-ethoxy)phenyl]-vinyl}quinoline 

Relevant academic research and scientific papers

Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids

A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.

Design, synthesis, biological evaluation and molecular docking studies of novel 3-aryl-4-anilino-2H-chromen-2-one derivatives targeting ERα as anti-breast cancer agents

The estrogen receptor (ER) has played an important role in breast cancer development and progression and is a central target for anticancer drug discovery. In order to develop novel selective ERα modulators (SERMs), we designed and synthesized 18 novel 3-aryl-4-anilino-2H-chromen-2-one derivatives based on previously reported lead compounds. The biological results indicated that most of the compounds presented potent ERα binding affinity and possessed better anti-proliferative activities against MCF-7 and Ishikawa cell lines than the positive control tamoxifen. The piperidyl substituted compounds such as 16d and 18d demonstrated strong ERα binding affinities and excellent anti-proliferative activities respectively. Compound 18d displayed the most potent ERα binding affinity with RBA value of 2.83%, while 16d exhibited the best anti-proliferative activity against MCF-7 cells with IC50 value of 4.52?±?2.47?μM. Further molecular docking studies were also carried out to investigate binding pattern of the newly synthesized compounds with ERα. All these results together with the structure–activity relationships (SARs) indicated that these 3-aryl-4-anilino-2H-chromen-2-one derivatives with basic side chain could serve as promising leads for further optimization as novel SERMs.

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.

Synthesis and biological evaluation of a new series of ebselen derivatives as glutathione peroxidase (GPx) mimics and cholinesterase inhibitors against Alzheimer's disease

A series of ebselen derivatives were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and glutathione peroxidase (GPx) mimics. Most of the compounds were found to be potent against AChEs and BuChE, compounds 5e and 5i, proved to be the most potent against AChE with IC50 values of 0.76 and 0.46 μM, respectively. Among these hybrids, most of the compounds were found to be good GPx mimics compare with ebselen. The selected compounds 5e and 5i were also used to determine the catalytic parameters and in vitro hydrogen peroxide scavenging activity. The results indicate that compounds 5e and 5i may be excellent multifunctional agents for the treatment of AD.

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.

Phenyl and pyridyl LTA4H modulators

Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and inflammatory conditions.

SUBSTITUTED HETEROCYCLIC COMPOUNDS AND METHODS OF USE

The present invention relates to hydroxybenzimidazole pyrimidines or pyridines or pharmaceutically-acceptable salts thereof. Also included is a method of treatment of inflammation, inhibition of T cell activation and proliferation, arthritis, rheumatoid arthritis, psoriatic arthritis, osteoarthritis, organ transplant, acute transplant or heterograft or homograft rejection, transplantation tolerance induction, ischemic or reperfusion injury, myocardial infarction, stroke, multiple sclerosis, inflammatory bowel disease, including ulcerative colitis, Crohn's disease, lupus, contact hypersensitivity, delayed-type hypersensitivity, and gluten-sensitive enteropathy, type 1 diabetes, psoriasis, contact dermatitis, Hashimoto's thyroiditis, Sjogren's syndrome, autoimmune hyperthyroidism, Addison's disease, autoimmune polyglandular disease, autoimmune alopecia, pernicious anemia, vitiligo, autoimmune hypopituatarism, Guillain-Barre syndrome, glomerulonephritis, serum sickness, uticaria, allergic diseases, asthma, hayfever, allergic rhinitis, scleracielma, mycosis fungoides, dermatomyositis, alopecia areata, chronic actinic dermatitis, eczema, Behcet's disease, Pustulosis palmoplanteris, Pyoderma gangrenum, Sezary's syndrome, atopic dermatitis, systemic schlerosis, morphea, atopic dermatitis, colon carcinoma or thymoma in a mammal comprising administering a therapeutically-effective amount a compound as described above.

Rapid and Efficient Synthesis of 1H-Indol-2-yl-1H-quinolin-2-ones

(Equation Presented) A concise and efficient synthesis of the novel indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitors 1-3 is presented.

Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers

The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested.Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation.However, related α-piperidino-ω-(4-substituted-phenoxy)alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long.Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed.Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a ?* intramolecular electron transfer excited state is produced.Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.