1703-34-0

Basic information

• Product Name: 4-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]morpholine
• Synonyms: 4-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]morpholine;LG-50043
• CAS NO: 1703-34-0
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.34
• Mol File: 1703-34-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 511.1°C at 760 mmHg
• Flash Point: 262.9°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 1.46E-10mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: 4-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]morpholine(1703-34-0)
• EPA Substance Registry System: 4-[1-Oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]morpholine(1703-34-0)

Safety Data

• Hazardous Substances Data: 1703-34-0(Hazardous Substances Data)

Usage

Classification

Morpholine derivative

Molecular Structure

Six-membered heterocyclic ring with two nitrogen atoms

Functional Groups

3,4,5-trimethoxyphenyl group
2-propenyl group

Potential Applications

Pharmaceuticals, agrochemicals, materials science

Note

Further research and testing needed for a comprehensive understanding of properties and applications.

InChI:InChI=1/C16H21NO5/c1-19-13-10-12(11-14(20-2)16(13)21-3)4-5-15(18)17-6-8-22-9-7-17/h4-5,10-11H,6-9H2,1-3H3/b5-4+

Upstream product

• 110-91-8 morpholine 
• 10263-19-1 (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 
• 682805-47-6 C₁₃H₁₄O₇ 
• 20329-96-8 methyl 3,4,5-trimethoxycinnamate 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1082730-34-4 (E)-N-methoxy-N-methyl-3-(3,4,5-trimethoxyphenyl)acrylamide 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 10263-19-1 3',4',5'-trimethoxycinnamoyl chloride 
• 90-50-6 3,4,5-trimethoxycinnamic acid 

Downstream Products

• 77664-07-4 (E)-1-Morpholin-4-yl-3-(3,4,5-trimethoxy-phenyl)-propenethione 

Relevant articles and documents

Design, synthesis and biological evaluation of (E)-3-(3,4,5-trimethoxyphenyl) acrylic acid (TMCA) amide derivatives as anticonvulsant and sedative agents

In this article, a novel series of (E)-3-(3,4,5-trimethoxyphenyl)acrylic acid (TMCA) amide derivatives 1-18 were designed and synthesized by a facile and one-pot step, which were achieved with good yields using 1-hydroxybenzotriazole (HOBT) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) as activation system. All the synthesized derivatives were biologically evaluated for their anticonvulsant, sedative activity and neurotoxicity using the maximal electroshock (MES) model, sc-pentylenetetrazol (PTZ) model, pentobarbital sodium-induced sleeping model, and locomotor activity tests, respectively. Among them, compounds 4, 9 and 16 exhibited good anticonvulsant activity in primary evaluation. Furthermore, compound 4 is the most effective anticonvulsant and sedative agent in subsequent tests, while the low threshold of toxicity of compound 4 is vigilant. Compounds 9 and 16 also performed significantly anticonvulsant activity in subsequent tests with weak toxicity. The molecular modeling experiments also predicted good binding interactions of the obtained active molecules with the GABA transferas. Therefore, it could be concluded that the synthesized derivatives 4, 9 and 16 would represent useful lead compounds for further investigation in the development of anticonvulsant and sedative agents.

Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship

In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, 1H, 13C nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 μM) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 μM; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 μM). This compound was also active against Candida tropicalis at 97.67 μM. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 μM) and more than five-fold less toxic (CC50: 231.71 μM) than piplartine (IC50: 315.33 μM and CC50: 41.14 μM) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.

A simple synthesis of trans-3,4,5-trimethoxycinnamamides and evaluation of their biologic activity

A simple synthesis and biologic evaluation of trans-3,4,5- trimethoxycinnamamides 10a-e and 11 as novel antinarcotic agents is described. The synthetic key strategies involve condensation reaction and coupling reaction to generate trans-3,4,5-trimethoxycinnamamides 10a-e and 11. They were evaluated for free radical scavenging, inhibitory action for neurotoxicity in cultured neurons, and antinarcotic activity in mice. It was found that compounds 10a, 10d, and 10e displayed significant inhibitory action of the glutamate-induced neurotoxicity and 10a-e and 11 showed high antinarcotic activity in mice.