88053-13-8

Basic information

• Product Name: 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• Synonyms: 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one;1-(1-Piperazinyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one;1-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]piperazine;1-(3,4,5-trimethoxycinnamoyl)piperazine;N-(3,4,5-trimethoxycinnamoyl)piperazine
• CAS NO: 88053-13-8
• Molecular Formula: C16H22N2O4
• Molecular Weight: 306.35688
• EINECS: 1533716-785-6
• Mol File: 88053-13-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 512.4 °C at 760 mmHg
• Flash Point: 263.7 °C
• Appearance: /
• Density: 1.15
• Vapor Pressure: 1.3E-10mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(88053-13-8)
• EPA Substance Registry System: 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(88053-13-8)

Safety Data

• Hazardous Substances Data: 88053-13-8(Hazardous Substances Data)

Usage

General Description

1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one is a chemical compound with a complex structure. It contains a piperazine ring and a prop-2-en-1-one functional group, as well as a phenyl ring with three methoxy substituents. 1-(piperazin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one may have potential applications in pharmaceuticals or research, as piperazine derivatives are known for their diverse biological activities, including antipsychotic and antidepressant properties. The presence of the phenyl ring and the prop-2-en-1-one group may also contribute to its functional properties, making it a potentially versatile and valuable chemical compound for further study and development.

InChI:InChI=1/C16H22N2O4/c1-20-13-10-12(11-14(21-2)16(13)22-3)4-5-15(19)18-8-6-17-7-9-18/h4-5,10-11,17H,6-9H2,1-3H3/b5-4+

Upstream product

• 110-85-0 piperazine 
• 10263-19-1 3',4',5'-trimethoxycinnamoyl chloride 
• 90-50-6 3,4,5-trimethoxycinnamic acid 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 10263-19-1 (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1878-29-1 ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 1374250-20-0 tert-butyl 4-[(E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl]-1-piperazinecarboxylate 

Downstream Products

• 88197-48-2 (E)-1-{4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Preparation method for cinepazide maleate

The invention provides a preparation method for cinepazide maleate, which comprises the following steps of: (1) carrying out Wittig reaction on 3, 4, 5-trimethoxybenzaldehyde serving as an initial rawmaterial and phosphine ylide to obtain (E)-3, 4, 5-trimethoxyethyl cinnamate (intermediate I), (2) hydrolyzing the (E)-3, 4, 5-trimethoxyethyl cinnamate to obtain a key intermediate 3, 4, 5-trimethoxy cinnamic acid (intermediate II), (3) in the presence of 1-hydroxybenzotriazole, triethylamine and carbodiimide hydrochloride, coupling the intermediate I with anhydrous piperazine to synthesize 1-(3, 4, 5-trimethoxycinnamoyl) piperazine (intermediate III), (4) reacting the 1-(3, 4, 5-trimethoxycinnamoyl) piperazine with 2-bromo-1 (pyrrolidine-1-yl) ethyl ketone to generate cinepazide (an intermediate IV), and (5) salifying the cinepazide in the step (4) and maleic acid to generate the target product cinepazide maleate. The preparation method has the advantages of cheap and easily available raw materials, simple operation, short production period, high yield, easy purification, good control of the product quality, reduction of the pollutant discharge, environmental protection, and realization of industrial production.

Synthesis and discovery of 18β-glycyrrhetinic acid derivatives inhibiting cancer stem cell properties in ovarian cancer cells

Despite advances in ovarian cancer treatment, the five-year overall survival rate is less than 30% with the presence of cancer stem cells (CSCs). To develop CSC-targeting therapy, a series of 18β-glycyrrhetinic acid (GA) derivatives containing cinnamamide moiety have been designed, synthesized, and screened for their antiproliferative activity in SKOV3 and OVCAR3 cells. Most of the compounds exhibited stronger antiproliferative activity than GA, and compound 7c was the most active one. Further biological studies showed that compound 7c could induce apoptosis and suppress migration. In addition, compound 7c could not only observably decrease the colony formation and sphere formation ability, but also significantly reduce the CD44+, CD133+, and ALDH+ subpopulation in SKOV3 and OVCAR3 cells. In conclusion, these results indicate that compound 7c is a promising anti-CSC agent for further anti-ovarian cancer studies.

Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors

A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.