20197-75-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3-dihydro-1,4-benzodioxine-6-carboxylic acid methyl ester is utilized as a key intermediate in the synthesis of various drugs and bioactive molecules. Its versatile chemical structure allows for the development of new pharmaceutical agents with potential therapeutic benefits.
Used in Medicinal Chemistry Research:
2,3-dihydro-1,4-benzodioxine -6-carboxylic acid methyl ester is employed as a starting material or a building block in the design and synthesis of novel drug candidates. Its unique structural features make it a valuable component in the creation of new chemical entities with potential applications in treating various diseases and conditions.
Used in Therapeutic Applications:
2,3-dihydro-1,4-benzodioxine-6-carboxylic acid methyl ester has been studied for its potential therapeutic properties, including anti-inflammatory and antioxidant effects. While further research is necessary to fully understand its pharmacological properties, its preliminary findings suggest that it may have beneficial effects in the treatment of inflammation and oxidative stress-related disorders.

InChI:InChI=1/C10H10O4/c1-12-10(11)7-2-3-8-9(6-7)14-5-4-13-8/h2-3,6H,4-5H2,1H3

Upstream product

• 67-56-1 methanol 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 91608-15-0 tris(2,4,6-trimethoxyphenyl)phosphine 
• 493-09-4 benzo-1,4-dioxane 
• 124-38-9 carbon dioxide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 4442-54-0 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid 
• 106-93-4 ethylene dibromide 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 29415-97-2 methyl 3-bromo-4-hydroxybenzoate 
• 325147-52-2 2-(2-bromo-4-carboxylic acid methyl ester phenoxy)-1-tert-butyldimethylsiloxyethane 
• 51329-16-9 3,4-dibromobenzoic acid methyl ester 
• 107-21-1 ethylene glycol 

Downstream Products

• 1338597-16-2 3-(benzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 
• 1338597-17-3 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(2-nitrobenzylthio)-4-phenyl-4H-1,2,4-trazole 
• 1338597-18-4 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(3-nitrobenzylthio)-4-phenyl-4H-1,2,4-trazole 
• 1338597-19-5 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(4-nitrobenzylthio)-4-phenyl-4H-1,2,4-trazole 
• 1338597-20-8 3-(2-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 
• 1338597-21-9 3-(3-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 
• 1338597-22-0 3-(4-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 
• 1338597-23-1 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(3-methoxybenzylthio)-4-phenyl-4H-1,2,4-triazole 
• 1338597-24-2 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(2-methylbenzylthio)-4-phenyl-4H-1,2,4-triazole 
• 1338597-25-3 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(4-methylbenzylthio)-4-phenyl-4H-1,2,4-triazole 
• 1338597-26-4 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(2-fluorobenzylthio)-4-phenyl-4H-1,2,4-triazole 
• 1338597-27-5 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(4-fluorobenzylthio)-4-phenyl-4H-1,2,4-triazole 
• 1338597-28-6 3-(2,4-difluorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 
• 1338597-29-7 3-(2,6-difluorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenyl-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Discovery of a series of 1,3,4-oxadiazole-2(3H)-thione derivatives containing piperazine skeleton as potential FAK inhibitors

Focal adhesion kinase (FAK) is an important drug target that plays a fundamental role in mediating signal transduction system. We report herein the discovery of a novel class of 1,3,4-oxadiazole-2(3H)-thione derivatives containing piperazine skeleton with

Oxadiazole derivatives containing 1,4-benzodioxan as potential immunosuppressive agents against RAW264.7 cells

A series of oxadiazole derivatives containing 1,4-benzodioxan (4a-4s) have been first synthesized for their potential immunosuppressive activity. Among the compounds, compound 4i showed the most potent biological activity against RAW264.7 cells (inhibition = 37.66 ± 2.34% for NO overproduction and IC50= 0.05 μM for iNOS). Docking simulation was performed to position compound 4i into the iNOS structure active site to determine the probable binding model. RT-PCR experiment results demonstrated that some of these compounds possessed good immunosuppressive activity against iNOS, especially for compound 4i. Therefore, compound 4i with potent inhibitory activity may be a potential agent.

Synthesis, structure, and urease inhibitory activities of Co(III), Mn(II) and Zn(II) complexes with hydrazone derived from protocatechuic acid

[CoIII(L1)2·H2O]NO3 (1), [MnII(L1)2·H2O] (2), and [ZnII(L1)2·H2O] (3) with a hydrazone derived from protocatechu

Synthesis, Biological Evaluation, and Molecular Docking of 1,4-Benzodioxan Derivatives as Potential Antibacterial Agents

A series of novel 1,4-benzodioxan derivatives containing Schiff base are synthesized by the method of splicing active substructures. All compounds are assayed for antimicrobial activity. The preliminary results indicate that most of the products demonstrate higher antibacterial activity against Gram-negative bacteria strains than Gram-positive bacteria strains. Compounds 4d and 4m exhibit better antibacterial activity against E. coli (MIC = 0.78 and 0.17 μg/mL), respectively; compound 4g displays better antibacterial activity against P. aeruginosa (MIC = 0.78 μg/mL). Eleven common antibacterial targets are selected for molecular docking of target compounds. The results demonstrate that all target compounds have the strongest binding energy to Tyrosine-tRNA synthetase (-CDOCKER_INTERACTION_ENERGY, kcal/mol: 47.1486 and 47.3776). Therefore, it is speculated that the target compounds can be used as novel tyrosine-tRNA synthetase inhibitors.

Synthesis and antioxidant activity of novel Mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan

A new series of Mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan (6a-6ae) were synthesized and characterized by 1H NMR, ESI-MS and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction. All these novel compounds were screened for their in vitro antioxidant activity employing 2,2′-diphenyl-1- picrylhydrazyl radical (DPPH), 2,2′-azinobis (3-ethylbenzothiazoline-6- sulfonate) cationic radical (ABTS+) and ferric reducing antioxidant power (FRAP) scavenging assays. Due to the combination of 1,4-benzodioxan, 1,3,4-oxadiazoles and substituted phenyl ring, most of them exhibited nice antioxidant activities. In all of these three assays mentioned above, compounds 6f and 6e showed significant radical scavenging ability comparable to the commonly used antioxidants, BHT and Trolox. Seven compounds with representative substituents or activities were selected for further assays in chemical simulation biological systems - inhibition of microsomal lipid peroxidation (LPO) and protection against 2,2′-azobis (2-amidinopropane hydrochloride) (AAPH) induced DNA strand breakage, in which, 6f and 6e were demonstrated to be of the most potent antioxidant activities.

Characterization and Crystal Structure of a Novel Mononuclear Cobalt(II) Complex with Hydrazone Derived from Protocatechuic Acid

A novel complex [CoII(L)2·CH3OH] with hydrazone derived from protocatechuic acid (HL=C16H14N2O4) is designed and synthesized. The complex is characterized by single crystal X-ray

BENZOXAZINONE COMPOUNDS AS KLK5/7 DUAL INHIBITORS

The present invention provides compounds and pharmaceutical compositions including the compounds for the treatment of a skin disease associated with proteolytic activity of one or more KLK proteases, wherein the compounds are according to formula (I): whe

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions

Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.

As the PI3K/mTOR inhibitor tricyclic compound, its preparation and use

The invention discloses a tricyclic compound as a PI3K/mTOR inhibitor. The tricyclic compound is a compound with the general formula (I) in the specification, wherein Ar is selected from aryl or heteroaryl; X, Y and Z are independently selected from O, CR2R3 and NR4 respectively; Q is selected from O, CR2R3 and NR4 or does not exists; R1 represents C1-C6 alkyl; n is selected from integers from 0 to 4; when n is more than or equal to 2, two R1 and a morpholine cycle can be combined into a combined cycle, a bridge cycle or a spiral cycle; R2 and R3 are selected from hydrogen and C1-C6 alkyl; R4 is selected from hydrogen, C1-C6 alkyl, C3-C7 cycloalkyl, heterocyclic radical, acyl and sulfonyl. The invention further discloses a perpetration method of the compound with the general formula (I) as well as a pharmaceutical composition and application of the compound with the general formula (I).