55486-27-6

Usage

Uses

Used in Pharmaceutical Industry:
1-CINNAMOYL-PIPERAZINE is used as an intermediate in the synthesis of various drugs, particularly for the development of antipsychotics and antidepressants. Its unique structure and pharmacological properties contribute to the creation of novel therapeutic agents with potential applications in mental health treatment.
Used in Neurological Disorders Treatment:
1-CINNAMOYL-PIPERAZINE is used as a potential neuroprotective agent for the treatment of neurological disorders. Its ability to exhibit central nervous system effects and its potential role in the treatment of such disorders highlight its value in drug discovery and development for neurological health.
Used in Anti-Inflammatory and Analgesic Applications:
1-CINNAMOYL-PIPERAZINE is used as an anti-inflammatory and analgesic agent due to its demonstrated effects in these areas. Its potential to alleviate pain and reduce inflammation makes it a candidate for the development of new medications targeting conditions that involve these symptoms.

InChI:InChI=1/C13H16N2O/c16-13(15-10-8-14-9-11-15)7-6-12-4-2-1-3-5-12/h1-7,14H,8-11H2/b7-6+

Upstream product

• 110-85-0 piperazine 
• 102-92-1 cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 7542-23-6 piperazine hydrochloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 84050-18-0 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline hydrochloride 

Relevant academic research and scientific papers

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

Design of enamides as new selective monoamine oxidase-B inhibitors

Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.

Preparing method of N-monosubstituted piperazine compound

The invention discloses a preparing method of an N-monosubstituted piperazine compound shown in the formula (6). Piperazine monohydrochloride (1) and RX or RCl react in solvent to prepare monosubstituted piperazine dihydrochloride (4) or (5), alkali is added for neutralizing, and the product (6) is obtained through rectification steaming.

1 - (cinnamoyl) - 4-piperidyl amide piperazine compound and its preparation method

The invention discloses a 1-(cinnamoyl)-4-piperidyl amide piperazidine compound and a preparation method thereof. The 1-(cinnamoyl)-4-piperidyl amide piperazidine compound is a compound shown as the formula (I) and pharmaceutically acceptable salt. The co

Synthesis, characterization, and anti-inflammatory activities of methyl salicylate derivatives bearing piperazine moiety

In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. The in vivo anti-inflammatory activities of target compounds were investigated against xylol-induced ear edema and carrageenan-induced paw edema in mice. The results showed that all synthesized compounds exhibited potent anti-inflammatory activities. Especially, the anti-inflammatory activities of compounds M15 and M16 were higher than that of aspirin and even equal to that of indomethacin at the same dose. In addition, the in vitro cytotoxicity activities and anti-inflammatory activities of four target compounds were performed in RAW264.7 macrophages, and compound M16 was found to significantly inhibit the release of lipopolysaccharide (LPS)-induced interleukin (IL)-6 and tumor necrosis factor (TNF)-α in a dose-dependent manner. In addition, compound M16 was found to attenuate LPS induced cyclooxygenase (COX)-2 up-regulation. The current preliminary study may provide information for the development of new and safe anti-inflammatory agents.

Cytotoxic Amides from Fruits of Kawakawa, Macropiper excelsum

Cytotoxic amides have been isolated from the fruits of the endemic New Zealand medicinal plant kawakawa, Macropiper excelsum (Piperaceae). The main amide was piperchabamide A and this is the first report of this rare compound outside the genus Piper. Elev

Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors

Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.

Pyrimidine Derivatives. 4. Synthesis and Antihypertensive Activity of 4-Amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline Derivatives

A series of 30 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline derivatives was prepared and tested for their ability to reduce blood pressure in conscious, spontaneously hypertensive rats (SHR).A number of these compounds, notably 4-amino-2-(4-