27578-60-5

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Aminoethyl)piperidine is used as a reactant for the synthesis of various pharmaceutical agents, including:
1. Analogs of anticancer agents, where it contributes to the development of novel treatments for cancer.
2. Inhibitors of botulinum neurotoxin serotype A light chain, which have potential applications in treating botulism and related conditions.
3. Treatments for P. falciparum malaria, where it is used to develop new drugs to combat this life-threatening disease.
4. Antiviral agents against the Ebola filovirus, which is a highly lethal and dangerous pathogen.
Used in Chemical Industry:
N-(2-Aminoethyl)piperidine is used in the modification of vinylbenzyl chloride/divinylbenzene gel copolymer bead, which is an important step in the creation of advanced materials with specific properties.
Used in Coordination Chemistry:
It is employed in the synthesis of linkage isomers such as trans-bis[1-(2-aminoethyl)piperidine]dinitronickel and trans-bis[1-(2-aminoethyl)piperidine]dinitritonickel, which are coordination compounds with potential applications in various fields.
Used in the Synthesis of Schiff Base Ligands:
N-(2-Aminoethyl)piperidine undergoes a [1+1] condensation reaction with 3-methoxy salicylaldehyde to yield tridentate Schiff base ligands, which are valuable in coordination chemistry and catalysis.
Used in the Development of Cannabinoid CB1 Receptor Antagonists:
It serves as a building block in the synthesis of cannabinoid CB1 receptor antagonists, which have potential therapeutic applications in various conditions, including obesity, metabolic syndrome, and certain neurological disorders.
Used in the Synthesis of Small Molecules for Colorectal Carcinoma Treatment:
N-(2-Aminoethyl)piperidine is used as a reactant in the development of small molecules that restore E-cadherin expression and reduce invasion in colorectal carcinoma cells, offering a potential therapeutic approach to this type of cancer.
Used in the Synthesis of Potent and Selective 5-HT6 Antagonists:
It is utilized in the creation of potent and selective 5-HT6 antagonists, which have potential applications in the treatment of cognitive disorders and other conditions related to the serotonin system.
Used in the Synthesis of N-Mustards as Anticancer Agents:
N-(2-Aminoethyl)piperidine is also used in the synthesis of N-mustards, a class of alkylating agents with proven efficacy in the treatment of various cancers.

InChI:InChI=1/C7H16N2/c1-7(8)9-5-3-2-4-6-9/h7H,2-6,8H2,1H3

Upstream product

• 151-56-4 ethyleneimine 
• 110-89-4 piperidine 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 926-39-6 sulfuric acid mono-(2-amino-ethyl ester) 
• 3010-03-5 piperidin-1-yl-acetonitrile 
• 111-24-0 1,5-dibromo-pentane 
• 6780-13-8 1,2-ethanediamine monohydrate 
• 64-17-5 ethanol 
• 107-15-3 ethylenediamine 
• 18169-21-6 nitro-1 N-piperidino-2 ethylene 
• 870-24-6 2-chloroethanamine hydrochloride 
• 79315-00-7 N-(2-Piperidin-1-yl-ethyl)-propionamide 
• 1932-03-2 2-(piperidin-4-yl)ethyl chloride 
• 57796-56-2 6-chloro-5-ethylamino-3-methoxy-pyrazine-2-carboxylic acid 2-piperidin-1-yl-ethylamide 

Downstream Products

• 10120-30-6 diphenyl-acetic acid-(2-piperidino-ethylamide) 
• 102453-41-8 1,1-diphenyl-2-(2-piperidino-ethylamino)-ethanol 
• 4746-88-7 2-hydroxy-2,2-diphenyl-N-(2-piperidin-1-yl-ethyl)-acetamide 
• 14299-34-4 4-isopentyloxy-benzoic acid-(2-piperidino-ethylamide) 
• 101739-47-3 2-phenyl-butyric acid-(2-piperidino-ethylamide) 
• 6715-02-2 N-(2-piperidino-ethyl)-bicyclohexyl-1-carboxamide 
• 100172-18-7 diethyl-(2-chloro-benzyl)-{2-[(2-piperidino-ethylaminooxalyl)-amino]-ethyl}-ammonium; chloride 
• 100792-41-4 (4-chloro-benzylidene)-(2-piperidino-ethyl)-amine 
• 100875-24-9 benzylidene-(2-piperidino-ethyl)-amine 
• 4380-82-9 N-(2-(piperidin-1-yl)ethyl)benzamide 
• 50594-18-8 N-phenyl-N'-(2-piperidino-ethyl)-urea 
• 92263-31-5 1-phenyl-3-(2-(piperidin-1-yl)ethyl)thiourea 

Relevant academic research and scientific papers

Insights into the mechanism of inhibition of CXCR4: Identification of piperidinylethanamine analogs as anti-HIV-1 inhibitors

The cellular entry of HIV-1 into CD4+ T cells requires ordered interactions of HIV-1 envelope glycoprotein with C-X-C chemokine receptor type 4 (CXCR4) receptors. However, such interactions, which should be critical for rational structure-based discovery of new CXCR4 inhibitors, remain poorly understood. Here we first determined the effects of amino acid substitutions in CXCR4 on HIV-1NL4-3 glycoprotein-elicited fusion events using site-directed mutagenesis-based fusion assays and identified 11 potentially key amino acid substitutions, including D97A and E288A, which caused >30% reductions in fusion. We subsequently carried out a computational search of a screening library containing～604,000 compounds, in order to identify potential CXCR4 inhibitors. The computational search used the shape of IT1t, a known CXCR4 inhibitor, as a reference and employed various algorithms, including shape similarity, isomer generation, and docking against a CXCR4 crystal structure. Sixteen small molecules were identified for biological assays based on their high shape similarity to IT1t, and their putative binding modes formed hydrogen bond interactions with the amino acids identified above. Three compounds with piperidinylethanamine cores showed activity and were resynthesized. One molecule, designated CX6, was shown to significantly inhibit fusion elicited by X4 HIV-1NL4-3 glycoprotein (50% inhibitory concentration [IC50], 1.9 μM), to inhibit Ca2+ flux elicited by stromal cell-derived factor 1α (SDF-1α) (IC50, 92 nM), and to exert anti-HIV-1 activity (IC50, 1.5 μM). Structural modeling demonstrated that CX6 bound to CXCR4 through hydrogen bond interactions with Asp97 and Glu288. Our study suggests that targeting CXCR4 residues important for fusion elicited by HIV-1 envelope glycoprotein should be a useful and feasible approach to identifying novel CXCR4 inhibitors, and it provides important insights into the mechanism by which small-molecule CXCR4 inhibitors exert their anti-HIV-1 activities.

New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.

Thiazole orange – Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19

In this report, we synthesized a series of TO conjugates containing different amino side chains and investigated their binding to telomeric G-quadruplex DNA (G4) using several biophysical methods including fluorometric titration and thermal denaturation monitored by fluorescence and circular dichroism. The composition of side chains strongly affects the binding of these molecules to G-quadruplex DNA. Incorporation of amino side chains increases the binding affinity of TO toward G4 but has a minimal effect on its selectivity for G4 over duplex DNA. The plausible binding modes are a synergistic effect of end-stacking and groove interactions as indicated by docking studies. Inhibition of human telomerase activity by TO derivatives was determined in vitro by the TRAP assay. Several derivatives can selectively inhibit the activity of telomerase over DNA polymerase at low concentrations. More significantly, TO-spermine conjugate (16) exhibits a remarkable effect on telomerase inhibition in the submicromolar range, which is comparable to the inhibition effect of a well-known G4 ligand, BRACO-19. Our results here provide guidance of utilizing TO derivatives as a viable scaffold to design novel G4 ligands, G4 probes, and potent telomerase inhibitors.

C-3 NOVEL TRITERPENONE WITH C-28 UREA DERIVATIVES AS HIV INHIBITORS

The present invention relates to C-3 novel triterpenone with C-28 urea derivatives of formula (I); or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, W, J and X are as defined herein. The present invention also relates to pharmaceutical compositions comprising compounds of formula (I) useful for the treatment of viral diseases and particularly HIV mediated diseases.

Isoflavone amide type derivative, preparation method and medical application thereof

The invention relates to the field of medicinal chemistry, and relates to an isoflavone amide type derivative, a preparation method and a medical application thereof, in particular to an isoflavone amide type derivative with the general formula (I), a preparation method thereof, medicine compositions including the isoflavone amide type derivative and a medical application thereof, especially an application of the isoflavone amide type derivative as a medicine for preventing or curing hyperlipemia, obesity or type II diabetes. The general formula (I) is shown in the description.

Synthesis and antitumor activity of 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety

We report herein the design and synthesis of a series of novel 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety. These newly synthesized derivatives were evaluated for in vitro activity against selected cancer cell lines by MTT assay. Results revealed that some compounds exhibit broad-spectrum antitumor potency, and the most active compound 23p (IC50: 2.357-3.012 μM) was found more potent than Sunitinib (IC50: 31.594-49.036 μM) against HepG2, A549 and Skov-3, respectively.

HIV INTEGRASE INHIBITORS

The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

Synthesis and characterization of N-substitutional ethylenediamine derivatives

N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.

USE OF (R) AND (S)-2-ARYL-PROPIONIC ACID DERIVATIVES AS ANTISEPTIC AGENTS

The present invention relates to the use of amides of (R) and (S)-2-aryl- propionic acids as antiseptic agents. The present invention also provides a pharmaceutical preparation including compounds of formula (I), having antiseptic properties for the treatment of gastrointestinal, muco-epidermal and epidermal infections. The present invention is related to pharmaceutical compositions containing an antiseptic agent carried in a suitable vehicle to provide mouthwashes, tablets, solutions, gels, creams and others. The formulations are applied topically to sites of gastrointestinal, muco-epidermal or epidermal infections. Compounds of present invention can be useful in the treatment of nausea, vomiting, bloating, diarrhea, constipation and oropharyngeal, esophageal, vaginal, rectal, nasal and other mucosal infections.

Tetracyclic benzimidazole derivatives and combinatorial libraries thereof

The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.