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, 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.

Pyridazinone derivative, and preparation method and medical application thereof

The invention provides a pyridazinone derivative, and a preparation method and a medical application thereof. O-formylbenzoic acid used as a raw material reacts with dimethyl phosphite to obtain dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate, the dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate reacts with 3-cyano-4-fluorobenzaldehyde in the presence of triethylamine to prepare (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile, and the (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile is reduced by hydrazine hydrate to prepare 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid; and benzaldehyde or substituted aromatic formaldehyde or furfural used as a raw material and malonic acid undergo a Knoevenagel reaction to obtain cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid, the cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid and 1-tert-butoxycarbonylpiperazine undergo an amidation reaction, a tert-butoxycarbonyl group is removed from the obtained amidation product in the presence of trifluoroacetic acid, and the obtained product and the 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid undergo the amidation reaction to obtain a series of (E)-4-{3-[4-[(3-substituted aryl)acryloyl]piperazin-1-carbonyl]-4-fluorobenzyl}-2H-pyridazin-1-one derivatives. Results of preliminary pharmacological activity screening show that the compound represented by a general formula shown in the present invention has a certain in-vitro PARP-1 inhibition ability and a certain in-vitro tumor cell proliferation resisting activity. The structural general formula of compound is shown in the description; and in the general formula, Ar is selected from two formulas also shown in the description, and R1, R2, R3, R3, R4 and R5 can be the hydrogen atom, the fluorine atom, the chlorine atom, the bromine atom, a methyl group, a methoxy group, a tetrafluoromethyl group and a nitro group.