28920-67-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-(4-methylpiperazin-1-yl)acetate is used as a building block for the synthesis of various drugs and compounds. Its versatile chemical structure allows for the development of new pharmaceuticals with potential therapeutic applications.
Used in Fragrance Industry:
Ethyl 2-(4-methylpiperazin-1-yl)acetate is used as a key component in certain fragrance compounds for its pleasant odor. Its unique scent profile contributes to the creation of various fragrances used in personal care products, perfumes, and other scented goods.
Used in Bioactive Molecule Research:
Ethyl 2-(4-methylpiperazin-1-yl)acetate is used as a bioactive molecule in research studies exploring its potential use in the treatment of various medical conditions. Its ability to interact with biological systems makes it a promising candidate for further investigation and development in the field of medicine.

InChI:InChI=1/C9H18N2O2/c1-3-13-9(12)8-11-6-4-10(2)5-7-11/h3-8H2,1-2H3

Upstream product

• 50398-09-9 N-methylpiperazine dihydrochloride 
• 105-39-5 chloroacetic acid ethyl ester 
• 109-01-3 1-methyl-piperazine 
• 105-36-2 ethyl bromoacetate 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 50677-34-4 1-methyl-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]piperazine 
• 672285-91-5 2-(4-ethylpiperazin-1-yl)acetic acid 
• 24632-44-8 4-methyl-1-piperazinylacetic acid hydrazide 
• 1407510-24-0 C₂₆H₃₁FN₄O₃ 
• 1300731-02-5 2-(4-methylpiperazin-1-yl)-N-((R)-1-phenylethyl)acetamide 
• 1300731-08-1 (R)-N-2-((4-methylpiperazin-1-yl)ethyl)-1-phenylethanamine 
• 114584-89-3 1-(2-hydroxy-2,2-diphenyl-ethyl)-1,4,4-trimethyl-piperazinediium; bis-methyl sulfate 
• 121968-99-8 1-benzyl-4-(2-hydroxy-2,2-diphenyl-ethyl)-1-methyl-piperazinium; bromide 
• 54699-92-2 (4-Methyl-piperazin-1-yl)-acetic acid 
• 21579-78-2 2-(4-methyl-piperazin-1-yl)-1,1-diphenyl-ethanol 

Relevant academic research and scientific papers

Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy,2-naphthyl)propionic acid (naproxen) for topical drug delivery

Various novel morpholinyl- (3a,b) and methylpiperazinylacyloxyalkyl (3c- f) esters of 2-(6-methoxy-2-naphthyl)propionic acid were synthesized and evaluated in vitro for topical drug delivery as potential prodrugs of naproxen (1). Compounds 3a-f were prepared by coupling the corresponding naproxen hydroxyalkyl ester with the morpholinyl- or (4-methyl-1- piperazinyl)acyl acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)-pyridine (DMAP) and quantitatively hydrolyzed (t(1/2) = 1- 26 min) to naproxen in human serum. Compounds 3c-f showed higher aqueous solubility and similar lipophilicity, determined by their octanol-buffer partition coefficients (log P(app)), at pH 5.0 when compared to naproxen. At pH 7.4 they were significantly more lipophilic than naproxen. The best prodrug 3c led to a 4-and 1.5-fold enhancement of skin permeation when compared to naproxen at pH 7.4 and 5.0, respectively. The present study indicates using a methylpiperazinyl group yields prodrugs that are partially un-ionized under neutral and slightly acidic conditions, and thus, a desirable combination is achieved in terms of aqueous solubility and lipophilicity. Moreover, the resulting combination of biphasic solubility and fast enzymatic hydrolysis of the methylpiperazinylacyloxyalkyl derivatives gave improved topical delivery of naproxen.

Synthesis, biological activities and docking studies of piperazine incorporated 1, 3, 4-oxadiazole derivatives

New series of 1, 3, 4-oxadiazoles incorporating piperazine scaffolds in a single molecular framework has been reported. The structures of the synthesized derivatives were assigned by IR, NMR and mass spectral techniques. The hybrid compounds were evaluated for their antimicrobial, antitubercular and antioxidant activities. The observed MIC values of anti-tubular activities for the molecule 3a, 3b, 3c, 3d and 3e were 6.25, 3.12, 3.12, 1.60 and 50.0 μg/ml respectively. As compared to ascorbic acid (IC50 = 62.91 μg/ml), molecule 3a exhibited better antioxidant activities (IC50 = 36.72 μg/ml). Also, all molecules have shown significant antimicrobial activities. In addition, docking simulations were performed to study ligand-protein interactions and to determine the probable binding conformations. In drug likeness model study compound 3b possessed maximum drug likeness model score (0.75) similar to the standard drug streptomycin. The compound 3a, 3b and 3c were emerged as potential derivatives in the series and could serve as lead compound for the development of potential therapeutic agents.

MODIFIED DRUGS FOR USE IN LIPOSOMAL NANOPARTICLES

Drag derivatives are provided herein which are suitable for loading into liposomal nanoparticle carriers. In some preferred aspects, the derivatives comprise a poorly water-soluble drag derivatized with a weak-base moiety that facilitates active loading of the drag through a LN transmembrane pH or ion gradient into the aqueous interior of the LN. The weak-base moiety can optionally comprise a lipophilic domain that facilitates active loading of the drag to the inner monolayer of the liposomal membrane. Advantageously, LN formulations of the drag derivatives exhibit improved solubility, reduced toxicity, enhanced efficacy, and/or other benefits relative to the corresponding free drags.

As tyrosine kinase inhibitors substituted indolinone derivatives

The invention belongs to the technical field of a medicine, and particularly relates to a substituted indole ketone derivative as a tyrosine kinase inhibitor shown in a general formula (I), a pharmaceutically acceptable salt, a deuterated article or a stereoisomer thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, Ra, Rb, Rc, Rd, n, n1, n2, n3, n4, a ring A and a ring B are defined in the specification. The invention also relates to a preparation method of the compound, a drug preparation containing the compound, and application of the compound in preparation of a drug for preventing or treating a fibrosis disease and treating an excessive hyperplasia disease.

Synthesis of a Gemcitabine Prodrug for Remote Loading into Liposomes and Improved Therapeutic Effect

The chemotherapeutic gemcitabine was actively and stably loaded into lipid nanoparticles through the formation of a prodrug. Gemcitabine was chemically modified to increase the lipophilicity and introduce a weak base moiety for remote loading. Several derivatives were synthesized and screened for their potential to be good liposomal drug candidates for remote loading by studying their solubility, stability, cytotoxicity, and loading efficiency. Two morpholino derivatives of GEM (22 and 23) were chosen as the preferred prodrugs for this purpose as they possessed the best loading efficiencies (100% for drug-to-lipid ratio of 0.36 w/w). This is a considerable improvement over a passive loading strategy where typical loading efficiencies are on the order of ～10-20% for a drug-to-lipid ratio of ～0.01. Liposomes loaded with these two prodrugs were studied in an s.c. tumor model in vivo and showed improved therapeutic effect over free GEM (～2-fold) and saline control (8- to 10-fold). This work demonstrates how chemical modification of a known hydrophilic drug can lead to improved loading, stability, and drug delivery in vivo.

PROTEIN KINASE INHIBITORS

A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.

Effect of a procaspase-activating compound on the catalytic activity of mature caspase-3

Caspase-3, an apoptosis-executing enzyme with a dimeric structure, and its zymogen (procaspase-3) are target proteins in cancer chemotherapy using synthetic compounds. Previous work has shown that PAC-1 (1st procaspaseactivating compound) affects the activation of procaspase-3 in cancerous cells through the Zn2+-chelation mechanism. However, we found that the compound also enhances the mature caspase-3 activity in the absence of Zn2+. The enhancement of the mature caspase-3 activity by PAC-1 followed a Michaelis-Menten-type saturation dependency with respect to the concentration of the compound. PAC-1 induced the change in the UV-vis spectrum of the mature caspase-3. From these findings, we propose a direct structural interaction of PAC-1 with the protein core. According to a molecular dynamics calculation for the complex of PAC-1 and mature caspase-3, PAC-1 is likely to bind to the interface between the dimeric structure in mature caspase-3. The interactions between PAC-1 and amino acid residues that affect the catalytic activity of mature caspase-3 are suggested. Throughout this work, diverse functions of the apoptosis-inducing compound are disclosed.

1,8-Naphthyridines IX. Potent anti-inflammatory and/or analgesic activity of a new group of substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6- carboxamides, of some their Mannich base derivatives and of one novel substituted 5-amino-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide derivative

A new group of 5-(alkylamino)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8] naphthyridine derivatives bearing a CONHR group at the 6-position (1c-g), designed to obtain new effective analgesic and/or anti-inflammatory agents, were synthesized and tested along with three new 9-alkyl-5-(4-alkyl-1-piperazinyl)- N,N-diethyl [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides (2b-d). Besides, a new class of analogues of compounds 1 and 2, bearing a Mannich base moiety at the 9-position (12a-d), as well as the novel N,N-diethyl-5- (isobutylamino)-8-methyl-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6- carboxamide (15) were prepared and tested. Compounds 1c-g exhibited very interesting anti-inflammatory properties in rats, whereas compounds 2b-d and 15 proved to be endowed with prevalent analgesic activity frequently associated with sedative effects in mice. On the contrary, the Mannich bases 12a-d resulted inactive. The most effective (80% inhibition of oedema) and potent (threshold dose 1.6 mg kg-1 with 31% inhibition of oedema) anti-inflammatory compound 1d did not show gastrolesive effects following 100 mg kg-1 oral administration in rats.

PROTEIN KINASE INHIBITORS

A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.

Design, synthesis and anti-itch activity evaluation of aromatic amino acid derivatives as gastrin-releasing peptide receptor antagonists

Eight aromatic amino acid derivatives (9a-9h) as gastrin-releasing peptide receptor (GRPR) antagonists were designed and synthesized. For the design, the tertiary structure of GRPR was predicted by blast searching in the premise of 1u19 protein as the template. Eight target compounds were docked into the binding pocket to investigate their possible binding interactions. Their anti-itch activities were tested by intrathecal injection using Kunming mice as experimental animals and chloroquine phosphate as a modeling medium. Compounds 9e and 9f significantly inhibited scratching behaviors. The anti-itch activities of these compounds decreased with the following sequence: 9e > 9f = 9d > 9b > 9g > 9a > 9h > 9c predicted by computer-aided drug design (CADD) and 9e > 9f > 9b > 9h > 9g > 9d > 9a > 9c evaluated by preliminary test. They were broadly in line with activity order pretested by CADD. It showed that the predicted tertiary structure of GRPR could be used for antipruritic drug design.