67869-90-3

Basic information

• Product Name: 3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE
• Synonyms: 3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE;3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBOXALDEHYDE;3,4-Dihydro-2H-1,5-benzodioxepin-7-carboxaldehyde;3,4-Dihydro-2h-1,5-benzodioxepine-7-carbaldehyde, 95+%;3,4-Dihydro-2H-1,5-benzodioxepin-7-carboxaldehyde 95%;3,4-Dihydro-2H-1,5-benzodioxepin-7-carboxaldehyde95%;3,4-Dihydro-2H-1,5-benzodioxepine-7-carboxaldehyde 95%;3,4-Dihydro-7-formyl-2H-1,5-benzodioxepine, 3,4-Dihydro-2H-benzo[b][1,4]dioxepine-7-carboxaldehyde
• CAS NO: 67869-90-3
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• Mol File: 67869-90-3.mol

Chemical Properties

• Boiling Point: 120-122
• Flash Point: 125.5°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE(67869-90-3)
• EPA Substance Registry System: 3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE(67869-90-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36-51
• Safety Statements: 26
• Hazardous Substances Data: 67869-90-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-2H-1,5-benzodioxepine-7-carbaldehyde is used as an intermediate in the synthesis of various pharmaceuticals and fine chemicals. Its unique chemical structure allows it to be a key component in the development of new drugs and therapeutic agents.
Used in Biological Research:
3,4-Dihydro-2H-1,5-benzodioxepine-7-carbaldehyde is used as a serotonin receptor agonist in biological research. Its potential biological activities are being studied to better understand its role in various physiological processes and to explore its potential as a therapeutic agent for various conditions.
Used in Food and Beverage Industry:
3,4-Dihydro-2H-1,5-benzodioxepine-7-carbaldehyde is used as a flavoring agent in the food and beverage industry. Its unique aroma and taste profile make it a valuable ingredient in the creation of new and innovative food products.

InChI:InChI=1/C10H10O3/c11-7-8-2-3-9-10(6-8)13-5-1-4-12-9/h2-3,6-7H,1,4-5H2

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 142-28-9 1,3-Dichloropropane 

Downstream Products

• 149744-50-3 (E)-3-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-(2-hydroxy-5-methyl-phenyl)-propenone 
• 136498-40-3 2-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-chroman-4-one 
• 149744-49-0 (E)-3-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-(5-fluoro-2-hydroxy-phenyl)-propenone 
• 149744-51-4 3-(1,5-benzodioxepan-7-yl)-1-(2-hydroxyphenyl)propen-1-one 
• 149744-53-6 (E)-3-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-(2-hydroxy-4-methoxy-phenyl)-propenone 
• 149744-62-7 (E)-3-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-(2-hydroxy-5-nitro-phenyl)-propenone 
• 941710-13-0 N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine 
• 1400250-97-6 C₂₄H₂₁BrN₄O₂ 
• 1400250-99-8 C₂₄H₂₁ClN₄O₂ 
• 1422156-19-1 C₂₀H₂₀N₂O₃ 
• 1422156-20-4 C₂₀H₁₉FN₂O₃ 
• 1422156-21-5 C₂₀H₁₉ClN₂O₃ 
• 1422156-22-6 C₂₀H₁₉BrN₂O₃ 
• 1422156-23-7 C₂₁H₂₂N₂O₃ 

Relevant articles and documents

Study of Schiff-base-derived with dioxygenated rings and nitrogen heterocycle as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

Fatty acid synthesis (FAS) is an essential metabolism during the whole growth and development process of the bacterial. Several key enzymes which involved in this biosynthetic pathway have been considered as useful targets for the development of new antibacterial agents. Among them, β-ketoacyl-acyl carrier protein synthase III (FabH) is the most magnetic target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved of both Gram-positive and Gram-negative bacteria. Following the previous researches, Schiff-based derivatives with dioxygenated rings and N-heterocycle were synthesized in succession, and their biological activities as potential FabH inhibitors were evaluated in this paper. Among these 15 compounds, compound 2E exhibited the best antibacterial activities with minimum inhibitory concentration (MIC) values 1.56-3.13 mg/mL against the tested bacterial strains and showed the most powerful Escherichia coli (E. coli) FabH inhibitory activities with IC50 of 2.1 μM. Also the conceivable binding conformation of placing compound 2E into the E. coli FabH active site was affirmed docking simulation.

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.

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.

Oxygen-containing benzo-cycloaliphatic amine compounds

The invention provides an oxygen-containing benzo-cycloaliphatic substituted amine compounds and application thereof and specifically relates to the oxygen-containing benzo-cycloaliphatic substitutedamine compounds as shown in a formula I which is described in the specification or pharmaceutically acceptable salts thereof and application of the same to preparation of Staphylococcus aureus goldenpigment synthesis inhibitor type antibacterial agents.

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.

4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity

Telomere and telomerase were closely related to the occurrence and development of some cancers. After the key active site of telomerase was identified, to enhance the ability of dihydropyrazole derivatives to inhibit telomerase, we designed a series of novel 4,5-dihydropyrazole derivatives containing heterocyclic oxygen moiety based on previous studies. The telomerase inhibition assay showed that compound 10a displayed the most potent inhibitory activity with an IC50 value of 0.6 μM for telomerase. The antiproliferative assay showed that 10a exhibited high activity against human gastric cancer cell SGC-7901 with an IC50 value of 10.95 ± 0.60 μM. Flow cytometric analysis and western blot results showed that 10a induced both apoptosis and autophagy. A docking simulation showed that 10a could bind well to the active site of telomerase and act as a telomerase inhibitor. The 3D-QSAR model was also built to provide a more pharmacological understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Novel Schiff-Base-Derived FabH Inhibitors with Dioxygenated Rings as Antibiotic Agents

Fatty acid biosynthesis plays a vital role in bacterial survival and several key enzymes involved in this biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. Of these promising targets, β-ketoacyl-acyl carrier protein (ACP) synthaseIII (FabH) is the most attractive target that could trigger the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and -negative bacteria. Designing small molecules with FabH inhibitory activity displays great significance for developing antibiotic agents, which should be highly selective, nontoxic and broad-spectrum. In this manuscript, a series of novel Schiff base compounds were designed and synthesized, and their biological activities were evaluated as potential inhibitors. Among these 21 new compounds, (E)-N-((3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methylene)hexadecan-1-amine (10) showed the most potent antibacterial activity with a MIC value of 3.89-7.81μM-1 against the tested bacterial strains and exhibited the most potent E.coli FabH inhibitory activity with an IC50 value of 1.6μM. Docking simulation was performed to position compound 10 into the E.coli FabH active site to determine the probable binding conformation.

Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors

A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC50 value of 0.9 μM for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC50 values of 18.07 and 5.34 μM, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Discovery of 6-substituted 4-anilinoquinazolines with dioxygenated rings as novel EGFR tyrosine kinase inhibitors

It had been reported that some dioxygenated rings fusing with the quinazoline scaffold could lead to new EGFR inhibitors. Based on this, several kinds of oxygenated alkane quinazoline derivatives were synthetized and evaluated as EGFR inhibitors. Their antiproliferative activities were tested against four cancer cell lines: A431, MCF-7, A549, and B16-F10. Most derivatives could counteract EGF-induced EGFR phosphorylation, and their potency was comparable to the reference compound Erlotinib. The size of the fused dioxygenated ring was crucial for the biological activity and the heptatomic ring derivative 19 showed potent in vitro inhibitory activity in the enzymatic assay as well as in the cellular assay.

5-Quinoline derivatives having an anti-bacterial activity

The present invention describes novel anti-bacterial compounds of the formula (I). These compounds are, amongst others, of interest as inhibitors of DNA gyrase and topoisomerases, for example of topoisomerase II and IV.