14939-91-4

Usage

Uses

Used in Synthetic Chemistry:
3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid is used as a building block in synthetic chemistry for its unique structural features. The presence of the benzodioxin ring and the acrylic acid group allows for the creation of various complex molecules and compounds, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Functional Materials:
3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid is used as a functional material in the development of advanced materials. 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid 's structure, particularly the dioxine ring and the acrylic acid group, can contribute to the properties of materials such as polymers, coatings, and adhesives. This makes it a potential candidate for applications in industries like electronics, automotive, and aerospace, where high-performance materials are required.
Used in Pharmaceutical Development:
3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid is used as a starting material in the development of new pharmaceuticals. 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid 's structure and the presence of the acidic moiety can be exploited to design and synthesize novel drug candidates with potential therapeutic applications. This can be particularly useful in the discovery of new treatments for various diseases and conditions, as well as in the improvement of existing medications.
Used in Agrochemical Formulation:
3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid is used as a component in the formulation of agrochemicals. 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)acrylic acid 's structure and reactivity can be utilized to create new pesticides, herbicides, or other agricultural chemicals that can improve crop yield and protect plants from pests and diseases. This can contribute to more sustainable and efficient agricultural practices.

InChI:InChI=1/C11H10O4/c12-11(13)4-2-8-1-3-9-10(7-8)15-6-5-14-9/h1-4,7H,5-6H2,(H,12,13)/p-1/b4-2+

Upstream product

• 141-82-2 malonic acid 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 110-89-4 piperidine 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 331-39-5 caffeic acid 

Downstream Products

• 491833-29-5 (1R,2R)-octanoic acid [2-(2',3'-dihydro-benzo[1,4]dioxin-6'-yl)-2-hydroxy-1-pyrrolidin-1-ylmethyl-ethyl]-amide 
• 491833-28-4 (1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol 

Relevant academic research and scientific papers

Synthesis of Piperine Analogs Containing Isoxazoline/Pyrazoline Scaffold and Their Pesticidal Bioactivities

In continuation of our program to discover new potential pesticidal agents, thirty-one piperine analogs containing isoxazoline/pyrazoline scaffold were prepared, and confirmed by infrared spectra, proton/carbon-13 nuclear magnetic resonance spectra, and high-resolution mass spectra. The structures of compounds VIIb and VIIIc were further determined by 1H-1H COSY spectra. Especially the configuration of compound VIIIc was unambiguously confirmed by single-crystal X-ray diffraction. Their pesticidal activities were evaluated against three serious and typically crop-threatening agricultural pests, Tetranychus cinnabarinus Boisduval (spider mite), Mythimna separata Walker (Oriental armyworm), and Plutella xylostella Linnaeus (diamondback moth). Compounds VIIIb and VIIIc exhibited greater than 40-fold more potent acaricidal activity than the lead compound piperine against T. cinnabarinus. Notably, compounds VIa-c exhibited more pronounced oral toxicity against P. xylostella than toosendanin; compounds VIb and VIc displayed more promising growth inhibitory activity against M. separata than toosendanin. It demonstrated that the methylenedioxy and isoxazoline scaffolds were important for the oral toxicity and growth inhibitory activity against P. xylostella and M. separata, respectively; the ethylenedioxy and isoxazoline scaffolds were vital for the acaricidal activity against T. cinnabarinus. Moreover, compounds VIb, VIIf, and VIIIc showed very low toxicity against NRK-52E cells.

Structure and urease inhibitory activity of copper(II) complex with (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid

A new caffeic acid derivative ((E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid, HL1)) is synthesized from caffeic acid, followed by the preparation of a Cu(II) complex, [Cu2(L1)4DMSO2]·2DMSO.

Design, synthesis and bioactivity evaluation of novel arylalkene-amide derivatives as dual-target antifungal inhibitors

Ergosterol as the core component of fungal cell membrane plays a key role in maintaining cell morphology and permeability. The squalenee epoxidase (SE) and 14-demethylase (CYP51) are the important rate-limiting enzymes for ergosterol synthesis. In the study, these active fragments, which is derived from the structural groups of the common antifungal agents, were docked into the active sites of dual targets (SE, CYP51), respectively. Some of active fragments with the matching MCSS_Score values were selected and connected to construct three different series of novel arylalkene-amide derivatives as dual-target (SE, CYP51) antifungal inhibitors. Subsequently, these compounds were further synthesized, and their bioactivity was evaluated. Most of compounds showed a certain degree of antifungal activity in vitro. It was worth noting that the target compounds 17a and 25a with excellent antifungal activity (0.125–4 μg/mL) can inhibit the fluconazole-resistant Candida Strain 17#, CaR, 632, and 901 in the range of MIC values (4–8 μg/mL). Furthermore, their molecular mechanism, structural stability and low toxicity were further confirmed. The molecular docking and ADMET properties were predicted to guide the subsequent optimization of target compounds.

STABLE N-((1R,2R)-1-(2,3-DIHYDROBENZO[B][1,4]DIOXIN-6-YL)-1-HYDROXY-3-(PYRROLIDIN-1-YL)PROPAN-2-YL) OCTANAMIDE (2R,3R)-2,3-DIHYDROXYSUCCINATE PREMIX AND PROCESS FOR PREPARATION THEREOF

The present invention related to stable N-((1R, 2R)-1-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)- 1-hydroxy-3- (pyrrolidin-1-yl)propan-2-yl) octanamide (2R,3R)- 2,3-dihydroxysuccinate premix of formula (Ia) and its process for preparation thereof. The present invention also related to process for the preparation of N-((1R, 2R)-1-(2,3-dihydrobenzo[b][1,4] dioxin-6- yl)-1-hydroxy-3- (pyrrolidin-1-yl) propan-2-yl) octanamide of formula (I) and pharmaceutically acceptable salts.

Structural optimization of caffeoyl salicylate scaffold as NO production inhibitors

Chlorogenic acid (CGA) has been considered as one of important active components in a number of medicinal herbs. Recently our group demonstrated that caffeoyl salicylate scaffold derived from CGA can be employed for the development of novel anti-inflammatory agents. The most active compound D104 can be a very promising starting point for the further structural optimization. A series of novel caffeoyl salicylate analogs were designed, synthesized, and evaluated by preliminary biological evaluation. The obtained results showed that the two compounds B12 and B13 can not only inhibit production of nitric oxide (NO) in RAW264.7 cells induced by lipopolysaccharides (LPS) effectively, but also have high safety in in vitro cytotoxic test, which could be comparable with D104. Molecular docking study on the peroxisome proliferator-activated receptor γ (PPARγ) protein revealed that compounds B12 and B13 can follow the same binding mode with D104, and the carboxyl group of caffeoyl salicylate scaffold might play a key role in the interaction with protein target, which implied the carboxyl group should be retained in the further optimization.

Design, synthesis, and anti-inflammatory activity of caffeoyl salicylate analogs as NO production inhibitors

Chlorogenic acid (CGA) has been reported to exhibit potent anti-inflammatory activity. However, the development of anti-inflammatory agent based on CGA has not been investigated. In this paper, a series of caffeoyl salicylate compounds derived from CGA were designed, synthesized, and evaluated by LPS-induced nitric oxide synthase inhibition and QRT-PCR technique. Most compounds showed modest activity to inhibit production of nitric oxide (NO) in RAW 264.7 cells induced by lipopolysaccharides (LPS). Among these compounds, QRT-PCR and western blotting results indicated that compounds 6b, 6c, 6f, 6g and D104 that possess 5-member ring or 6-member ring caused a significant inhibition against expression of the iNOS2 in LPS-induced macrophages. In addition, cytotoxic assay displayed most derivatives have good safety in vitro. This new promising scaffold could be further exploited for the development of anti-inflammatory agent in the future.

Optimization of substituted cinnamic acyl sulfonamide derivatives as tubulin polymerization inhibitors with anticancer activity

A new series of novel cinnamic acyl sulfonamide derivatives were designed and synthesized and evaluated their anti-tubulin polymerization activities and anticancer activities. One of these compounds, compound 5a with a benzdioxan group, was observed to be an excellent tubulin inhibitor (IC50 = 0.88 μM) and display the best antiproliferative activity against MCF-7 with an IC50 value of 0.17 μg/mL. Docking simulation was performed to insert compound 5a into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent anti-tubulin polymerization activity.

2-ACYLAMINOBENZAMIDE DERIVATIVES AND PREVENTIVE AND REMEDY FOR DISEASES CAUSED BY THE SUPERMULTIPLICATION OF VASCULAR INTIMAL CELLS

The present invention relates to 2-acylaminobenzamide derivatives represented by the general formula: wherein R1, R2, R3, R4and R5represent each a hydrogen atom etc.; X represents a vinylene group etc.; B represents a group represented by the general formula: -N(R6)(R7)wherein R6and R7represent each a hydrogen atom etc., a group represented by the general formula: -NH-(CH2)n-A-R8wherein A represents a single bond etc.; R8represents a hydroxy group etc. or a hydroxyamino group which are useful as agents for the prevention and treatment of diseases caused by excessive proliferation of vascular intimal cells.