10288-72-9

Usage

Uses

Used in Organic Synthesis:
6-Hydroxy-1,4-benzodioxane is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for the creation of complex organic molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Hydroxy-1,4-benzodioxane is used as a precursor for the development of new drugs. Its chemical properties make it suitable for the synthesis of bioactive molecules with potential therapeutic applications.
Used in Chemical Industry:
6-Hydroxy-1,4-benzodioxane is also utilized in the chemical industry for the production of specialty chemicals, such as dyes, pigments, and fragrances. Its ability to form a variety of chemical bonds makes it a valuable component in the synthesis of these products.
Used in Research and Development:
6-Hydroxy-1,4-benzodioxane serves as a valuable compound in research and development settings, where it is used to explore new chemical reactions and investigate the properties of novel organic molecules. Its unique structure and reactivity make it an interesting subject for scientific study.

InChI:InChI=1/C8H8O3/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-2,5,9H,3-4H2

Upstream product

• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 78541-20-5 40tert-butoxy-1,2-ethylenedioxybenzene 
• 164014-95-3 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid 
• 57744-67-9 6-iodo-1,4-benzodioxane 
• 107-21-1 ethylene glycol 
• 106-51-4 p-benzoquinone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 52287-51-1 6-bromo-1,4-benzodioxane 
• 120-80-9 benzene-1,2-diol 
• 493-09-4 benzo-1,4-dioxane 
• 782471-87-8 formic acid 2,3-dihydro-benzo[1,4]dioxin-6-yl ester 
• 7159-14-0 2,3-dihydro-1,4-benzodioxin-6-yl acetate 
• 22013-33-8 6-amino-3,4-benzodioxane 

Downstream Products

• 226400-22-2 C₂₅H₂₉NO₇S 
• 10288-82-1 2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)oxy)acetic acid 
• 1222555-14-7 1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one 

Relevant academic research and scientific papers

SYNTHESE D'UN ANALOGUE DIOXINIQUE DU PSORALENE

The synthesis of a new analog of psoralen built on a benzodioxinic moiety have been efficiently achieved using as a key intermediate the 6-hydroxy 7-formyl 1,4-benzodioxan.

Synthesis of a benzodioxinic analog of 8-methoxypsoralen

A synthesis of a benzodioxinic analog of 8-methyoxypsoralen (8-MOP), in 12 steps from the commercially available 6-acetyl-2,3-dihydro-1,4-benzodioxin is described.

Synthesis and antifungal activity of 2-hydroxy-4,5-methylenedioxyaryl ketones as analogues of kakuol

In a study aiming to determine the structural elements essential to the antifungal activity of kakuol, we synthesized a series of 2-hydroxy-4,5- methylenedioxyaryl ketones, and we assayed their in vitro antifungal activity. The most sensitive target organisms to the action of these class of compounds were Phytophthora infestans, Phytium ultimum, Cercospora beticola, Cladosporium cucumerinum, and Rhizoctonia solani. Most of the analogs showed a remarkable in vitro activity, and some of them appeared significantly more effective than the natural product. The biological activity was mainly affected by introducing structural modification on the carbonyl moiety of the natural-product molecule. In particular, compound 5a, bearing a C=C bond conjugated to the C=O group, was found active with a MIC value of 10 μg ml-1 against Cladosporium cucumerinum. The results suggest that 2-hydroxy-4,5-methylenedioxyaryl ketones can be considered promising candidates in the development of new antifungal compounds.

Compound with HMG-CoA reductase inhibitory activity, pharmaceutical composition and application thereof

The invention belongs to the field of biological medicines, and particularly discloses a compound shown as a formula I and used for treating and/or preventing HMG-CoA reductase related diseases or pharmaceutically acceptable salt or ester of the compound. The invention also discloses a pharmaceutical composition containing the compound. In addition, the invention also provides an application of the compound as an HMG-CoA reductase inhibitor and in preparation of drugs for treating and/or preventing HMG-CoA reductase related diseases. The compound provided by the invention has relatively strong activity of inhibiting HMG-CoA reductase, the prepared medicine is expected to have a relatively good effect on treating and/or preventing dyslipidemia and atherosclerosis, and the compound is relatively simple in structure and relatively low in expected price. In addition, the structure of the compound provided by the invention is completely different from that of the existing statins, and the phenomenon of drug resistance to the existing statins can be overcome.

From off-to on-target: New BRAF-inhibitor-template-derived compounds selectively targeting mitogen activated protein kinase kinase 4 (MKK4)

The mitogen-activated protein kinase (MAP) kinase 4 (MKK4) was found to be a major regulator of liver regeneration and could be a valuable drug target addressing liver related diseases by restoring its intrinsic regenerative capacity. We report on the synthesis and optimization of novel MKK4 inhibitors following a target-hopping strategy from the FDA-approved BRAFV600E inhibitor PLX4032 (8). Applying an iterative multi-parameter optimization process we carved out essential structural features yielding in compounds with a low nanomolar affinity for MKK4 and excellent selectivity profiles against the main off-targets MKK7 and JNK1, which, upon relevant inhibition, would totally abrogate the pro-regenerative effect of MKK4 inhibition, as well as against the off-targets MAP4K5, ZAK and BRAF with selectivity factors ranging from 40 to 430 for our best-balanced compounds 70 and 73.

CONDENSED HETEROCYCLIC COMPOUND HAVING 1,4-BENZO DIOXANE RING OR SALT THEREOF, AND ANTI-JUVENILE HORMONE AGENT COMPOSED OF THE COMPOUND

PROBLEM TO BE SOLVED: To provide a pest control agent containing a practical juvenile hormone antagonist activity compound as an active ingredient. SOLUTION: By using a reporter gene assay system that uses a juvenile hormone sequence, a heterocyclic compound having an antagonist activity is discovered, and a pest control agent containing the compound as an active ingredient is provided. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

Bimetallic photoredox catalysis: Visible light-promoted aerobic hydroxylation of arylboronic acids with a dirhodium(ii) catalyst

We report the use of a rhodium(II) dimer in visible light photoredox catalysis for the aerobic oxidation of arylboronic acids to phenols under mild conditions. Spectroscopic and computational studies indicate that the catalyst Rh2(bpy)2(OAc)4 (1) undergoes metal-metal to ligand charge transfer upon visible light irradiation, which is responsible for catalytic activity. Further reactivity studies demonstrate that 1 is a general photoredox catalyst for diverse oxidation reactions.

PROTEIN KINASE INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to MKK4 (mitogen-activated protein kinase 4) and their use in promoting liver regeneration or reducing or preventing hepatocyte death. The MKK4 inhibitors selectively inhibit protein kinase MKK4 over protein kinases JNK and MKK7.

Design, synthesis and characterization of potent microtubule inhibitors with dual anti-proliferative and anti-angiogenic activities

Microtubule has been an important target for anticancer drug development. Here we report the discovery and characterization of a series of fused 4-aryl-4H-chromene-based derivatives as highly potent microtubule inhibitors. Among a total of 37 derivatives synthesized, 23 exhibited strong in vitro anti-proliferative activities against A375 human melanoma cells. The relationship between the biological activities of these microtubule inhibitors and their chemical structure variations was analyzed. Studies of compounds 27a, 19a and 9a in parallel with colchicine as the positive control compound in a panel of biological assays revealed that these compounds blocked cell cycle progression, increased apoptosis, and inhibited HUVEC capillary tube formation at low nanomolar concentrations. The most potent compound 27a was also tested in eight additional cancer cell lines besides A375 cells and two non-cancer cells and showed potent and selective activity on these cancer cells. To understand the molecular and structure mechanism of action of these compounds, tubulin polymerization and molecular docking studies were carried out for 27a as the representative. The results were consistent with the mechanism by which 27a interacts with the colchicine binding site on tubulin and disrupts tubulin polymerization. With potent dual actions of microtubule destabilization and vascular disruption described above, this small molecule can serve as a valuable research probe of the function and role of microtubules in human diseases and promising lead for developing new therapeutic agents.

Biogenic synthesis of Fe2O3@SiO2 nanoparticles for ipso-hydroxylation of boronic acid in water

Here, biogenic synthesis of Fe2O3@SiO2 nanoparticles using fruit extract of Zanthoxylum rhetsa is reported. The SiO2 nanoparticles was synthesized using paddy straw which is a byproduct obtained in cultivation of rice. The composite was characterised by spectroscopic method like XRD, SEM, TEM and EDX analysis. The ipso-hydroxylation reactions were carried out with excellent yield within a moderate time period with mild reaction condition in all cases. Therefore, this approach may be considered as simple, easy, cheap and greener, environment friendly protocol for ipso-hydroxylation of arylboronic acids at 50 °C temperature.