23173-76-4

Usage

Uses

Used in Recreational Drug Industry:
1-Benzyl-4-(ethoxycarbonylmethyl)piperazine is used as a recreational drug for its stimulant and empathogenic effects, often sold in the form of tablets or powder and commonly used in party and club settings. However, it poses a risk of negative side effects such as increased heart rate, anxiety, and potential neurotoxicity with prolonged or excessive use. Due to these risks, the compound is regulated in many countries and is illegal to possess or distribute without proper authorization.

InChI:InChI=1/C15H22N2O2/c1-2-19-15(18)13-17-10-8-16(9-11-17)12-14-6-4-3-5-7-14/h3-7H,2,8-13H2,1H3

Upstream product

• 2759-28-6 1-phenylmethylpiperazine 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 100-44-7 benzyl chloride 
• 40004-08-8 1-(Ethoxycarbonylmethyl)piperazine 
• 623-73-4 diazoacetic acid ethyl ester 
• 5321-63-1 dihydrochloride salt of 1-benzylpiperazine 

Downstream Products

• 119929-87-2 1-benzyl-4-carboxymethylpiperazine 
• 1075725-60-8 2-(4-benzylpiperazin-1-yl)-N'-(3,5-diallyl-2-hydroxybenzylidene)acetohydrazide 
• 315183-21-2 2-(4-benzylpiperazin-1-yl)-N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide 
• 1075725-59-5 C₂₀H₂₃N₇O₂ 
• 1075725-57-3 N'-(3-allyl-2-methoxybenzylidene)-2-(4-benzylpiperazin-1-yl)acetohydrazide 
• 1075725-71-1 2-(4-benzylpiperazin-1-yl)-N-(2-hydroxyphenethyl)acetamide 
• 315183-08-5 de-allyl PAC-1 
• 1075725-70-0 2-(4-benzylpiperazin-1-yl)-N-(2-hydroxybenzyl)acetamide 
• 1449679-58-6 2-(4-benzylpiperazin-1-yl)-N'-(2-(bis(pyridin-2-ylmethyl)amino)acetyl)acetohydrazide 
• 1449679-59-7 (E)-2-(4-benzylpiperazin-1-yl)-N'-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)acetohydrazide 
• 24632-70-0 2-(4-benzylpiperazin-1-yl)acetohydrazide 
• 121677-69-8 1-benzyl-4-(2-hydroxy-2,2-diphenyl-ethyl)-1-methyl-piperazinium; methyl sulfate 
• 121968-99-8 1-benzyl-4-(2-hydroxy-2,2-diphenyl-ethyl)-1-methyl-piperazinium; bromide 
• 102946-58-7 2-(4-phenethyl-piperazino)-1,1-diphenyl-ethanol 

Relevant academic research and scientific papers

Synthesis, molecular modeling and evaluation of novel N′-2-(4- benzylpiperidin-/piperazin-1-yl)acylhydrazone derivatives as dual inhibitors for cholinesterases and Aβ aggregation

To develop new drugs for treatment of Alzheimer's disease, a group of N′-2-(4-Benzylpiperidin-/piperazin-1-yl)acylhydrazones was designed, synthesized and tested for their ability to inhibit acetylcholinesterase, butyrylcholinesterase and aggregation of a

Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: Comparison with TPEN and PAC-1

The lipophilic, cell-penetrating zinc chelator N,N,N′,N′,- tetrakis(2-pyridylmethyl) ethylenediamine (TPEN, 1) and the zinc chelating procaspase-activating compound PAC-1 (2) both have been reported to induce apoptosis in various cell types. The relations

DESIGN, SYNTHESIS AND EVALUATION OF PROCASPASE ACTIVATING COMPOUNDS AS PERSONALIZED ANTI-CANCER DRUGS

Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed that have lower neurotoxicity effects than other compounds.

Ruthenium(III) chloride-catalyzed efficient protocol for ethyl diazoacetate insertion into the N-H bond of secondary amines

Ruthenium(III) chloride (1 mol%) alone can catalyze the insertion of ethyl diazoacetate into N-H bonds of various structurally and electronically diverse secondary cyclic amines under solvent-free conditions to afford the corresponding glycine esters in g

COMPOSITIONS AND METHODS INCLUDING CELL DEATH INDUCERS AND PROCASPASE ACTIVATION

Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3. In embodiments, compositions are capable of activation of procaspase-3.

SELECTIVE APOPTOTIC INDUCTION IN CANCER CELLS INCLUDING ACTIVATION OF PROCASPASE-3

Compounds and related methods for synthesis, and the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3, and particular embodiments are capable of direct activation of procaspase-3 and procaspase-7 to the effector forms of caspase-3 and caspase-7. Procaspase-3 levels can vary among cancer cell types; several types have relatively high levels and can have increased susceptibility to chemotherapy by compounds and methods herein. Therapeutic applications are relevant for a variety of cancer conditions and cell types, e.g. breast, lung, brain, colon, renal, adrenal, melanoma, and others.

Design of selective peptidomimetic agonists for the human orphan receptor BRS-3

New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

Pyrimidine derivatives and processes for the preparation thereof

The present invention relates to novel pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing the same as an active ingredient, their novel intermediates, and processes for the preparation thereof wherein: when A is piperidin-1-yl or —NH—B, wherein B is C3-C4alkyl, C3-C4alkenyl, C3-C7cycloalkyl, C1-C3alkoxyethyl, phenylethl which may be substituted or unsubstituted, 3-trifluoromethylphenylmethyl, 1-naphthylmethyl, 4-methylthiazol-2-yl or 4-phenylthiazol-2-yl, R1is hydrogen or methyl; and R2, R3, R4and R5are hydrogen; or when A is a group of formula (II); when R1is hydroxymethyl or C1-C3alkoxymethyl, R2, R3, R4, R5and R6are hydrogen; and R7is hydrogen or halogen; or when R1is hydrogen or methyl, R7is hydrogen or halogen; and one or two of R2, R3, R4, R5and R6is hydroxy, methoxy, or a group of formula (III) wherein Z is C1-C4alkyl, substituted or unsubstituted C1-C4alkenyl, cyloalkyl, benzyloxyalkyl, alkoxycarbonylalkyl, morpholinomethyl, piperidinomethyl, 4-substituted-piperazinomethyl, substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted benzyl, thiophen-2-yl-methyl, 1-substituted-pyrrolidin-2-yl or —CHR8NHR9, wherein R8is hydrogen, methyl, isopropyl, benzyl, benzyloxymethyl, methylthioethyl, benzyloxycarbonylmethyl, carbamolymethyl, carbamoylethyl, or 1-benzylimidazol-4-ylmethyl and R9is hydrogen or t-butoxycarbonyl; and the others are hydrogen or methyl.

Design, synthesis, and structure-activity relationships of a series of 3-[2-(1-benzylpiperidin-4-yl)ethylamino]pyridazine derivatives as acetylcholinesterase inhibitors

Starting from the 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6-phenylpyridazine 1, we performed the design, the synthesis, and the structure-activity relationships of a series of pyridazine analogues acting as AChE inhibitors. Structural modifications were achieved on four different parts of compound 1 and led to the following observations: (i) introduction of a lipophilic environment in the C-5 position of the pyridazine ring is favorable for the AChE-inhibitory activity and the AChE/BuChE selectivity; (ii) substitution and various replacements of the C-6 phenyl group are possible and led to equivalent or slightly more active derivatives; (iii) isosteric replacements or modifications of the benzylpiperidine moiety are detrimental to the activity. Among all derivatives prepared, the indenopyridazine derivative 4g was found to be the more potent inhibitor with an IC50 of 10 nM on electric eel AChE. Compared to compound 1, this represents a 12-fold increase in potency. Moreover, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-5-methyl-6-phenylpyridazine 4c, which showed an IC50 of 21 nM, is 100-times more selective for human AChE (human BuChE/AChE ratio of 24) than the reference compound tacrine.

New aminoalkylchromones, processes for the preparation thereof

The invention relates to compounds of the general formula (I): STR1 wherein R 1, R 2, R 3, R 4, R 5, R 6 and Z are as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base and medicament