72551-53-2

Usage

Uses

Used in Medicinal Chemistry:
ETHYL 1-BENZYLPIPERIDINE-3-CARBOXYLATE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its structural features allow it to be a promising candidate in the development of new drugs with potential therapeutic applications.
Used in Drug Development:
In the pharmaceutical industry, ETHYL 1-BENZYLPIPERIDINE-3-CARBOXYLATE is utilized as a key component in the design and synthesis of novel drug molecules. Its presence in these molecules can influence their pharmacological properties, such as potency, selectivity, and bioavailability, making it a valuable asset in the drug discovery process.
Used in Research and Development:
ETHYL 1-BENZYLPIPERIDINE-3-CARBOXYLATE serves as a valuable research tool in academic and industrial laboratories. It can be used to study the structure-activity relationships of various drug candidates and to investigate the mechanisms of action of different pharmacological agents.
Used in Chemical Synthesis:
As a member of the piperidine family, ETHYL 1-BENZYLPIPERIDINE-3-CARBOXYLATE can be employed as a building block in the synthesis of more complex organic molecules. Its versatility in chemical reactions allows it to be a useful component in the preparation of a wide range of compounds with diverse applications.

InChI:InChI=1/C15H21NO2/c1-2-18-15(17)14-9-6-10-16(12-14)11-13-7-4-3-5-8-13/h3-5,7-8,14H,2,6,9-12H2,1H3

Upstream product

• 71962-74-8 Ethyl nipecotate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 72551-50-9 N-benzyl-3-(ethoxycarbonyl)pyridinium bromide 

Downstream Products

• 94379-05-2 (R,S)-N-benzylpiperidine-3-carboxamide 
• 50585-89-2 3-methoxycarbonylpiperidine 
• 182919-58-0 (±)-1-benzylpiperidine-3-carbohydrazide 
• 141943-04-6 1-benzylpiperidine-3-carboxylic acid 
• 310454-71-8 ethyl 1-benzyl-3-piperidinecarboxylate 1-methiodide 
• 85387-44-6 1-benzyl-3-(hydroxymethyl)piperidine 
• 145022-00-0 1-benzyl-3-formylpiperidine 
• 1047675-60-4 ethyl 1-benzyl-3-(3-bromopropyl)piperidine-3-carboxylate 
• 145022-01-1 1-benzyl-3-(formylmethyl)piperidine 
• 307532-02-1 3-amino-1-benzylpiperidine dihydrochloride 
• 478828-62-5 (1-benzylpiperidin-3-yl)carbamic acid tert-butyl ester 
• 50586-10-2 1-Benzyl-3-methylenepiperidin-2-one 

Relevant academic research and scientific papers

Novel 1,5-diaryl pyrazole-3-carboxamides as selective COX-2/sEH inhibitors with analgesic, anti-inflammatory, and lower cardiotoxicity effects

COX-2 selective drugs have been withdrawn from the market due to cardiovascular side effects, just a few years after their discovery. As a result, a new series of 1,5-diaryl pyrazole carboxamides 19–31 was synthesized as selective COX-2/sEH inhibitors wit

Synthesis, bioactivity and molecular modeling studies on potential anti-Alzheimer piperidinehydrazide-hydrazones

A group of N-benzylpiperidine-3/4-carbohydrazide-hydrazones were designed, synthesized and evaluated for acetylcholinesterase (AChE), butyrylcholinesterase (BuChE)activities, Aβ42 self-aggregation inhibitory potentials, and antioxidant capacities, in vitro. All of the compounds displayed eeAChE and huAChE inhibitory activity in a range of IC50 = 5.68–11.35 μM and IC50 = 8.80–74.40 μM, respectively and most of the compounds exhibited good to moderate inhibitory activity on BuChE enzyme. Kinetic analysis and molecular modeling studies were also performed for the most potent compounds (1g and 1j). Not only the molecular modeling studies but also the kinetic analysis suggested that these compounds might be able to interact with the catalytic active site (CAS)and the peripheral anionic site (PAS)of the enzymes. In the light of the results, compound 1g and compound 1j may be suggested as lead compounds for multifunctional therapy of AD.

Synthesis, biological evaluation, docking study and ulcerogenicity profiling of some novel quinoline-2-carboxamides as dual COXs/LOX inhibitors endowed with anti-inflammatory activity

A series of novel quinoline-2-carboxamides 15–28 was synthesized and evaluated in?vitro as dual COXs/LOX inhibitors. Compounds 19 and 27 exhibited the highest potency and selectivity for COX-2 inhibitory activity (IC50?=?1.21 and 1.13?μM, respe

Systematic Investigation into the Matsuda-Heck Reaction of α-Methylene Lactones: How Conformational Constraints Direct the β-H-Elimination Step

α-Methylene-γ-butyrolactone and α-methylene-δ-valerolactone undergo Pd-catalyzed Matsuda-Heck couplings with arene diazonium salts to α-benzyl butenolides or pentenolides, respectively, or to α-benzylidene lactones. The observed regioselectivity is strongly ring size dependent, with six-membered rings giving exclusively α-benzyl pentenolides, whereas the five-membered α-methylene lactone reacts to mixtures of regioisomers with a high proportion of (E)-α-benzylidene-γ-butyrolactones. DFT calculations suggest that the reasons for these differences are not thermodynamic but kinetic in nature. The relative energies of the conformers of the Pd σ-complexes resulting from insertion into the Pd-aryl bond were correlated with the dihedral angles between Pd and endo-β-H. This correlation revealed that in the case of the six-membered lactone an energetically favorable conformer adopts a nearly synperiplanar Pd/endo-β-H arrangement, whereas for the analogous Pd σ-complex of the five-membered lactone the smallest Pd/endo-β-H dihedral angle is observed for a conformer with a comparatively high potential energy. The optimized conditions for Matsuda-Heck arylations of exo-methylene lactones were eventually applied to the synthesis of the natural product anemarcoumarin A.

A simple iridicycle catalyst for efficient transfer hydrogenation of n-heterocycles in water

A cyclometalated iridium complex is shown to catalyse the transfer hydrogenation of various nitrogen heterocycles, including but not limited to quinolines, isoquinolines, indoles and pyridinium salts, in an aqueous solution of HCO2H/HCO2Na under mild conditions. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), with catalyst loadings as low as 0.01 mol % being feasible. Mechanistic investigation of the quinoline reduction suggests that the transfer hydrogenation proceeds via both 1,2- and 1,4-addition pathways, with the catalytic turnover being limited by the step of hydride transfer. An easily accessible iridicycle catalyst effects the transfer hydrogenation of a wide variety of N-heterocycles in water, including quinolines, isoquinolines, indoles, quinoxalines, and pyridines. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), even with low catalyst loadings.

1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds

Compounds of formula (I): wherein: A represents a divalent radical: wherein: Z represents an oxygen atom or a sulphur atom,R6 represents a hydrogen atom, an alkyl, alkenyl, arylalkyl or polyhaloalkyl group or a substituted, linear or branched alkyl chain, represents a single bond or a double bond,R1, R2, R3 and R4 represent a hydrogen or halogen atom,an alkyl, alkoxy, hydroxy, cyano, nitro, polyhaloalkyl or optionally substituted amino group, or a linear or branched alkyl chain substituted by one or more groups,R5 represents a hydrogen atom or an alkyl, aminoalkyl or hydroxyalkyl group,X and Y represent a hydrogen atom or an alkyl group,Ra, Rb, Rc and Rd represent a hydrogen or halogen atom, an alkyl, hydroxy, alkoxy, cyano, nitro, polyhaloalkyl, optionally substituted amino group, or a substituted, linear or branched alkyl chain,Re represents a hydrogen atom or an alkyl, arylalkyl or alkenyl group or a substituted, linear or branched alkyl chain, their enantiomers, diastereoisomers, and N-oxides, and also addition salts thereof with a pharmaceutically acceptable acid or base.

SUBSTITUTED CYCLOHEXYL DERIVATIVES AS NK-3 RECEPTOR ANTAGONISTS

The present invention relates to the compounds of formula (I): wherein A,B, n, X, Y, Z, R1, R2, R3, R4, R5, R6, R7 and R8 are defined herein, and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising them and their use in treating diseases mediated by neurokinin-3 (NK-3) receptors. These compounds can thus be used in methods of treatment to suppress and treat such disorders.

BENZAMIDE DERIVATIVES

A compound represented by formula (1): wherein X is a single bond or a substituted or unsubstituted lower alkylene group; Z is a saturated or unsaturated monocyclic hydrocarbon ring group or the like; and each of R1, R2, R3 and R4, which may be the same or different, is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a carboxyl group, a substituted or unsubstituted alkyl group, or the like, a prodrug of said compound, or a pharmaceutically acceptable salt of said compound or prodrug has inhibitory effect on Rho kinase and hence is useful for treating diseases which are such that morbidity due to them is expected to be improved by inhibition of Rho kinase and secondary effects such as inhibition of the Na+/H+ exchange transport system caused by the Rho kinase inhibition, for example, hypertension.

Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters

In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT 1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [(-)-15b, (-)-15j, (-)-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.