21057-39-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(CHLOROACETYL)-4-(2-METHOXYPHENYL)PIPERAZINE HYDROCHLORIDE is used as a serotonin receptor antagonist for the treatment of various neurological and psychiatric disorders. Its action on serotonin pathways makes it a potential candidate for addressing conditions related to serotonin dysregulation.
1-(CHLOROACETYL)-4-(2-METHOXYPHENYL)PIPERAZINE HYDROCHLORIDE is also used as a valuable tool in neuroscience research and drug development. 1-(CHLOROACETYL)-4-(2-METHOXYPHENYL)PIPERAZINE HYDROCHLORIDE's ability to modulate serotonin pathways provides insights into the underlying mechanisms of neurological and psychiatric disorders, aiding in the creation of novel therapeutic strategies.
The hydrochloride salt form of 1-(CHLOROACETYL)-4-(2-METHOXYPHENYL)PIPERAZINE HYDROCHLORIDE is commonly utilized due to its improved solubility and stability, which enhances its pharmaceutical applications and effectiveness in treatment.

InChI:InChI=1/C13H17ClN2O2/c1-18-12-5-3-2-4-11(12)15-6-8-16(9-7-15)13(17)10-14/h2-5H,6-10H2,1H3

Upstream product

• 5464-78-8 1-(2-methoxyphenyl)piperazine hydrochloride 
• 79-04-9 chloroacetyl chloride 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 

Downstream Products

• 155204-28-7 1-(2-methoxyphenyl)-4-(2-(2-pyridylamino)ethyl)piperazine 
• 220383-44-8 1-(N-phenyl-2-aminoethyl)-4-(2-methoxyphenyl)-piperazine 
• 1026084-24-1 (+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone 
• 1026084-30-9 (-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone 
• 43091-72-1 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine 

Relevant academic research and scientific papers

A new n-substituted 1h-isoindole-1,3(2h)-dione derivative— synthesis, structure and affinity for cyclooxygenase based on in vitro studies and molecular docking

Isoindoline-1,3-dione derivatives constitute an important group of medicinal substances. In this study, nine new 1H-isoindole-1,3(2H)-dione derivatives and five potential pharmacophores were obtained in good yield (47.24–92.91%). The structure of the new

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

Synthesis and in vivo Anti-inflammatory Evaluation of Piperazine Derivatives Containing 1,4-Benzodioxan Moiety

Six piperazine derivatives 6a–f containing 1,4-benzodioxan moiety have been synthesized and characterized by 1H NMR, ESI-MS and elemental analysis. The structure of 6d was further confirmed by single crystal X-ray diffraction. All these novel c

Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells

Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC50 = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity on yeast α-glucosidase while analogues 5 (IC50 16.4 μM) and 11 (IC50 16.6 μM) exhibited a 2-fold enhanced inhibitory activity on NO-production than betulinic acid.

Design, synthesis and biological profiling of aryl piperazine based scaffolds for the management of androgen sensitive prostatic disorders

In the quest for novel scaffolds for the management of androgen sensitive prostatic disorders like prostate cancer and benign prostatic hyperplasia, a series of twenty-six aryl/heteroaryl piperazine derivatives have been described. Three compounds, 8a, 8c

Molecular design and synthesis of 1,4-disubstituted piperazines as α1-adrenergic receptor blockers

A new series of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid amide and 3,5,6,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin- 4-one derivatives were designed, synthesized, their binding and functional properties as α1-adrenorec

Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl)ethyl] propylamino}-5,6,7,8-tetrahydronaphthalen-2-ol: Identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity

In the current report, we extend the SAR study on our hybrid structure 7-{[2-(4-phenyl-piperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen- 2-ol further to include heterocyclic bioisosteric analogues. Binding assays were carried out with HEK-29

2-[(3-Methoxyphenylethyl)phenoxy]-based ABCB1 inhibitors: Effect of different basic side-chains on their biological properties

Recently, 2-[(3-methoxyphenylethyl)phenoxy]-moiety has been selected for the design and synthesis of new small ABCB1 inhibitors. In the present paper, this moiety has been linked through a spacer of 2-5 carbon atoms to the nitrogen of three different basic nuclei such as: (i) N-4-arylpiperazine, (ii) N-4-methylpiperazine, and (iii) 6,7-dimethoxytetrahydroisoquinoline. The results demonstrated that all the selected basic nuclei were well tolerated and that, globally, the best inhibitory activity for each series was obtained when the spacer between the 2-[(3-methoxyphenylethyl)phenoxy] moiety and the basic nucleus consisted of a four-carbon chain. Among the synthesized compounds, N-4-methylpiperazine- 10c (IC50 = 0-15 μM) and tetrahydroisoquinoline-derivatives 11c (IC50 = 0.08 μM) with the spacer n = 4 for both series, displayed the best potency to inhibit ABCB1 activity. Moreover, for each compound, the ABCB1 interacting mechanism has been evaluated by three combined biological assays. N-4-methylpiperazine- (10a-d) and tetrahydroisoquinoline- (11a-d) derivatives were Cyclosporin A-like ABCB1 nontransported substrates.

The development of additional radioligands of varying pharmacokinetics for the 5-HT1A receptor

Six compounds have been prepared to further probe the structure activity relationships based on the 5-HT1A receptor ligand, WAY 100635. The goal is to obtain a series of radiotracers with varying pharmacokinetic properties. Substitution of a pyrimidine moiety, increased the specific binding ratio in the phenylcarboxamide series, but decreased the ratio in the cyclohexanecarboxamide series. A series of compounds with varying pharmacokinetic properties are now available to study a range of properties involving 5-HT1A receptor binding.