206273-87-2

Basic information

• Product Name: 4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 1-N-BOC-4-(BENZYLAMINO)PIPERIDINE;1-BOC-4-BENZYLAMINO-PIPERIDINE;4-BENZYLAMINO-1-BOC-PIPERIDINE;4-BENZYLAMINOPIPERIDINE, 1-BOC PROTECTED;4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;TERT-BUTYL 4-(BENZYLAMINO)PIPERIDINE-1-CARBOXYLATE;1-BOC-4-BENZYLAMINOPIPERIDIN;4-(Benzylamino)piperidine, N1-BOC protected
• CAS NO: 206273-87-2
• Molecular Formula: C₁₇H₂₆N₂O₂
• Molecular Weight: 290.4
• Mol File: 206273-87-2.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 398.115 °C at 760 mmHg
• Flash Point: 194.573 °C
• Appearance: /
• Density: 1.076 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(206273-87-2)
• EPA Substance Registry System: 4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(206273-87-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 206273-87-2(Hazardous Substances Data)

Usage

General Description

"4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER" is a chemical compound that falls under the category of piperidine carboxylic acid derivatives. It consists of a piperidine ring with a benzylamino group attached to it, and a carboxylic acid tert-butyl ester functional group. 4-BENZYLAMINO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is commonly used as a building block in organic synthesis and medicinal chemistry, where it can be utilized in the creation of various pharmaceuticals and biologically active molecules. Additionally, it may also have potential applications in research and development processes within the chemical and pharmaceutical industries.

InChI:InChI=1/C17H26N2O2/c1-17(2,3)21-16(20)19-11-9-15(10-12-19)18-13-14-7-5-4-6-8-14/h4-8,15,18H,9-13H2,1-3H3

Upstream product

• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 100-52-7 benzaldehyde 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 100-46-9 benzylamine 
• 1402047-78-2 C₁₇H₂₄N₂O₂ 
• 100-39-0 benzyl bromide 
• 144-55-8 sodium hydrogencarbonate 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 420136-94-3 N-benzyl-4-aminopiperidine 

Relevant articles and documents

Linker-switch approach towards new ATP binding site inhibitors of DNA gyrase B

Due to increasing emergence of bacterial resistance, compounds with new mechanisms of action are of paramount importance. One of modestly researched therapeutic targets in the field of antibacterial discovery is DNA gyrase B. In the present work we synthesized a focused library of potential DNA gyrase B inhibitors composed of two key pharmacophoric moieties linked by three types of sp3-rich linkers to obtain three structural classes of compounds. Using molecular docking, molecular dynamics and analysis of conserved waters in the binding site, we identified a favourable binding mode for piperidin-4-yl and 4-cyclohexyl pyrrole-2-carboxamides while predicting unfavourable interactions with the active site for piperazine pyrrole-2-carboxamides. Biological evaluation of prepared compounds on isolated enzyme DNA gyrase B confirmed our predictions and afforded multiple moderately potent inhibitors of DNA gyrase B. Namely trans-4-(4,5-dibromo-1H-pyrrole-2-carboxamide)cyclohexyl)glycine and 4-(4-(3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamido)piperidin-1-yl)-4-oxobutanoic acid with an IC50value of 16 and 0.5?μM respectively.

Synthesis and Biological Evaluation of Fentanyl Analogues Modified at Phenyl Groups with Alkyls

A series of fentanyl analogues modified at the phenyl group of the phenethyl with alkyl and/or hydroxyl and alkoxy, and the phenyl group in the anilido moiety replaced with benzyl or substituted benzyl, were synthesized. The in vitro opioid receptor functional activity of these compounds was evaluated by assessment of their ability to modulate forskolin-stimulated cAMP accumulation and by their ability to induce β-arrestin2 recruitment. Compound 12 is a potent μ-opioid (MOP) receptor agonist, a potent κ-opioid (KOP) receptor antagonist with weak β-arrestin2 recruitment activity. Compounds 10 and 11 are potent MOP receptor agonists with weak δ-opioid (DOP) receptor antagonist activity and moderate KOP receptor antagonist activity as well as weak β-arrestin2 recruitment activity at the MOP receptor. These compounds are promising leads for discovery of potent opioid analgesics with reduced side effects relative to clinically available strong opioid analgesics.

Discovery of an Orally Bioavailable Inhibitor of Defective in Cullin Neddylation 1 (DCN1)-Mediated Cullin Neddylation

We previously reported the discovery, validation, and structure-activity relationships of a series of piperidinyl ureas that potently inhibit the DCN1-UBE2M interaction. We demonstrated that compound 7 inhibits both the DCN1-UBE2M protein-protein interaction and DCN1-mediated cullin neddylation in biochemical assays and reduces levels of steady-state cullin neddylation in a squamous carcinoma cell line harboring DCN1 amplification. Although compound 7 exhibits good solubility and permeability, it is rapidly metabolized in microsomal models (CLint = 170 mL/min/kg). This work lays out the discovery of an orally bioavailable analogue, NAcM-OPT (67). Compound 67 retains the favorable biochemical and cellular activity of compound 7 but is significantly more stable both in vitro and in vivo. Compound 67 is orally bioavailable, well tolerated in mice, and currently used to study the effects of acute pharmacologic inhibition of the DCN1-UBE2M interaction on the NEDD8/CUL pathway.