160706-62-7

Basic information

• Product Name: (R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER
• Synonyms: D-1-CBZ-NIPECOTIC ACID;(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER;(R)-1-CBZ-PIPERIDINE-3-CARBOXYLIC ACID;(R)-1-[(BENZYLOXY)CARBONYL]PIPERIDINE-3-CARBOXYLIC ACID;(R)-1-Benzyloxycarbonylnipecotic acid;3(R)-N-(Carbobenzyloxy)-3-carboxypiperidine;(R)-1-CBZ-PIPERIDINE-1-CARBOXYLIC ACID;1-Cbz-(3R)-3-piperidinecarboxylic acid
• CAS NO: 160706-62-7
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.29
• Mol File: 160706-62-7.mol

Chemical Properties

• Boiling Point: 443.9°C at 760 mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.265
• Vapor Pressure: 1.16E-08mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• PKA: 4.48±0.20(Predicted)
• CAS DataBase Reference: (R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER(160706-62-7)
• EPA Substance Registry System: (R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER(160706-62-7)

Safety Data

• Hazardous Substances Data: 160706-62-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER is used as a key intermediate for the synthesis of various pharmaceutical drugs due to its potential medicinal properties and its role as a building block in drug development.
Used in Drug Formulation:
(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER is used as an ingredient in drug formulation to improve the stability and solubility of the final product, thanks to its benzyl ester form.
Used in Pharmaceutical Research and Development:
(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER is used as a subject of investigation for its potential anti-inflammatory and analgesic properties, contributing to the advancement of pharmaceutical research and development in these therapeutic areas.

InChI:InChI=1/C14H17NO4/c16-13(17)12-7-4-8-15(9-12)14(18)19-10-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H,16,17)/t12-/m1/s1

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 163343-71-3 (R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate 
• 78190-11-1 1-benzyloxycarbonylpiperidine-3-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 498-95-3 (R)-nipecotic acid 

Downstream Products

• 1050446-94-0 C₁₄H₁₈N₂O₃ 
• 1044560-96-4 (R)-benzyl 3-aminopiperidine-1-carboxylate 
• 309956-78-3 (R)-piperidin-3-ylcarbamic acid tert-butyl ester 
• 912807-36-4 (R)-1-[(1R,2R,3S)-3-{(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy}-2-(4-fluorophenyl)cyclopentylmethyl]piperidine-3-carboxylic acid tert-butyl ester 
• 912807-35-3 (R)-3-N-tert-butoxycarbonylaminopiperidine 
• 1419221-77-4 benzyl (3R)-3-([(3-chloropyrazin-2-yl)methyl]carbamoyl)piperidine-1-carboxylate 
• 1419214-70-2 (R)-4-(8-amino-3-(piperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide 

Relevant articles and documents

Pipecolic esters as minimized templates for proteasome inhibition

Allosteric regulators of clinically important enzymes are gaining popularity as alternatives to competitive inhibitors. This is also the case for the proteasome, a major intracellular protease and a target of anti-cancer drugs. All clinically used proteasome inhibitors bind to the active sites in catalytic chamber and display a competitive mechanism. Unfortunately, inevitable resistance associated with this type of inhibition drives the search for non-competitive agents. The multisubunit and multicatalytic “proteolytic machine” such as the proteasome is occasionally found to be affected by agents with other primary targets. For example the immunosuppressive agent rapamycin has been shown to allosterically inhibit the proteasome albeit at levels far higher than its mTOR related efficacy. As part of an ongoing program to search for novel proteasome-targeting pharmacophores, we identified the binding domain of rapamycin as required for proteasome inhibition even without the macrocyclic context of the parent compound. By subsequent structure-activity relationship studies, we generated a pipecolic ester derivative compound 3 representing a new class of proteasome inhibitors. Compound 3 affects the core proteasome activities and proliferation of cancer cells with low micromolar/high nanomolar efficacy. Molecular modeling, atomic force microscopy imaging and biochemical data suggest that compound 3 binds into one of intersubunit pockets in the proteasomal α ring and destabilizes the α face and the gate. The α face is used as a docking area for proteasome-regulating protein modules and the gate is critical for controlling access to the catalytic chamber. Thus, the pipecolic ester template elicits a new and attractive mechanism for proteasome inhibition distinct from classical competitive drugs.

PIPECOLIC ESTERS FOR INHIBITION OF THE PROTEASOME

The present disclosure relates to chemical compounds that modulate proteasome activity, pharmaceutical compositions containing such compounds, and use of these compounds and compositions for the treatment of disorders of uncontrolled cellular proliferation such as, for example, a cancer. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

(R)- 3 - Boc - amino piperidine preparation method

The invention discloses a preparation method of (R)-3-Boc-aminopiperidine and relates to the technical field of preparation of piperidine heterocyclic compounds. The preparation method includes following steps: (1) with N-Cbz-3-piperidinecarboxylic acid as a raw material, performing chiral resolution with R-phenylethylamine to obtain a compound I; (2) performing an acid-amide condensation reaction to the compound I and ammonia gas to obtain a compound II; (3) performing a Hofmann degradation reaction to the compound II to obtain a compound III; (4) performing protection to the compound III with di-tert-butyl dicarbonate to obtain a compound IV; and (5) performing a hydrogenation and Cbz-removal reaction to the compound IV to prepare the (R)-3-Boc-aminopiperidine. The method is mild in reaction conditions, is safe and reliable, is excellent in process stability, is low in energy consumption, is high in yield, is green and environment-protective and is suitable for industrial production.

Potent direct inhibitors of factor Xa based on the tetrahydroisoquinoline scaffold

Direct inhibition of coagulation factor Xa (FXa) carries significant promise for developing effective and safe anticoagulants. Although a large number of FXa inhibitors have been studied, each can be classified as either possessing a highly flexible or a rigid core scaffold. We reasoned that an intermediate level of flexibility will provide high selectivity for FXa considering that its active site is less constrained in comparison to thrombin and more constrained as compared to trypsin. We studied several core scaffolds including 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid for direct FXa inhibition. Using a genetic algorithm-based docking and scoring approach, a promising candidate 23 was identified, synthesized, and found to inhibit FXa with a Ki of 28 μM. Optimization of derivative 23 resulted in the design of a potent dicarboxamide 47, which displayed a Ki of 135 nM. Dicarboxamide 47 displayed at least 1852-fold selectivity for FXa inhibition over other coagulation enzymes and doubled PT and aPTT of human plasma at 17.1 μM and 20.2 μM, respectively, which are comparable to those of clinically relevant agents. Dicarboxamide 47 is expected to serve as an excellent lead for further anticoagulant discovery.

INHIBITORS OF PROTEIN KINASES

Compounds of general Formula I, wherein R1, R2, R3, x, A and Ra are as defined herein are inhibitors of cyclin-dependent kinases and are useful for preventing and/or treating any type of pain, inflammatory disorders, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases and neurodegenerative diseases.

SUCCINATE SALTS OF HETEROCYCLIC DPP-IV INHIBITORS

The present invention relates to therapeutically active and selective hemisuccinate salts of inhibitors of the enzyme DPP-IV of formula (I), pharmaceutical compositions comprising the salts and the use of such salts for and the manufacture of medicaments for treating diseases that are associated with proteins that are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

HETEROCYCLIC COMPOUNDS THAT ARE INHIBITORS OF THE ENZYME DPP-IV

The present invention relates to therapeutically active and selective inhibitors of the enzyme DPP-IV of formula I, pharmaceutical compositions comprising the compounds and the use of such compounds for and the manufacture of medicaments for treating diseases that are associated with proteins that are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

Methods for the stereoselective synthesis of substituted piperidines

One aspect of the present invention relates to methods of synthesizing substituted piperidines. A second aspect of the present invention relates to stereoselective methods of synthesizing substituted piperidines. The methods of the present invention will