326-56-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 1,3-benzodioxole-5-carboxylate serves as an intermediate in the synthesis of various drugs, particularly those with sedative and anxiolytic properties. Its chemical structure contributes to the development of medications that address anxiety and promote relaxation.
Used in Fragrance Industry:
Leveraging its aromatic properties, methyl 1,3-benzodioxole-5-carboxylate is utilized as a fragrance ingredient in perfumes and other personal care products. It enhances the scent profiles of these products, providing a pleasant and lasting aroma.
It is crucial to handle and store methyl 1,3-benzodioxole-5-carboxylate with care due to its potential health and environmental hazards if not properly managed.

InChI:InChI=1/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)/p-1

Upstream product

• 186581-53-3 diazomethane 
• 94-53-1 Piperonylic acid 
• 67-56-1 methanol 
• 120-57-0 piperonal 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 124-41-4 sodium methylate 
• 214334-34-6 1,1,6,6-tetramethoxy-1,6-bis(3,4-methylenedioxyphenyl)hexane 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 333-27-7 methyl trifluoromethanesulfonate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61599-80-2 methyl 6-iodo-2H-benzo1,3-dioxolene-5-carboxylate 
• 69048-76-6 6-iodo-1,3-benzodioxole-5-methanol 
• 495-76-1 piperonol 
• 61441-09-6 methyl 6-bromo-1,3-benzodioxole-5-carboxylate 

Downstream Products

• 857832-29-2 benzo[1,3]dioxol-5-yl-bis-(2-methoxy-phenyl)-methanol 
• 81581-27-3 ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 94-53-1 Piperonylic acid 
• 145102-04-1 methyl 3-<(propylthio)methoxy>-4-hydroxybenzoate 
• 133789-62-5 (R)-1-<3',4'-(methylenedioxy)phenyl>-2-(p-tolylsulfinyl)ethan-1-one 
• 133642-15-6 C₂₁H₂₇N₂O₆P 
• 133658-66-9 C₂₄H₃₁N₂O₆P 
• 89084-30-0 2-diphenylphosphinoyl-1-(3,4-methylenedioxyphenyl)propan-1-one 
• 56882-48-5 5-(3,4-methylenedioxyphenyl)-2,3,5,6-tetrahydroimidazo[2,1-a]isoquinolin-5-ol 
• 495-76-1 piperonol 
• 356560-89-9 1-(benzo[1,3]dioxol-5-yl)-2-(6-methylpyridin-2-yl)ethanone 

Relevant academic research and scientific papers

Novel furfurylidene N-acylhydrazones derived from natural safrole: Discovery of LASSBio-1215, a new potent antiplatelet prototype

We describe herein the discovery of (E)-N-methyl-N'-((5-nitrofuran-2-yl) methylene)benzo[d]1,3 dioxole-5-carbohydrazide (9e), named LASSBio-1215, as a novel antiplatelet agent belonging to the N-methyl-N-acylhydrazone class, which exert their antiaggregating actions on human and rabbit platelets induced by different agonists, through cyclooxygenase-1 (COX-1) or thromboxane synthase inhibition. This compound was elected after screening of a series of functionalized furyl N-acylhydrazone derivatives, synthesized from natural safrole 10. In vitro assays showed that compound 9e presents platelet-aggregating activity in rabbit platelet-rich plasma (PRP) induced by arachidonic acid (IC50=0.7 M) and collagen (IC50=4.5 M). Moreover, LASSBio-1215 also inhibited almost completely the second wave of adenosine diphosphate-induced platelet aggregation in human PRP, and this effect was correlated with their ability to block the production of pro-aggregating autacoid thromboxane A2.

Design, synthesis, crystal structure, molecular docking studies of some diorganotin(IV) complexes derived from the piperonylic hydrazide Schiff base ligands as cytotoxic agents

Inspired by the role of organotin(IV) complexes in inhibition of cancer cell growth and interaction with different target proteins, we have synthesized a series of new organotin(IV) complexes of Schiff base ligands of benzylidene benzohydrazide analogues. The structural elucidation of compounds was done by spectroscopic studies showing tridentate nature (NOO) of Schiff base ligands having pentacoordinated geometry around the central tin metal. The X-ray crystallographic study of complex 9 (Me2SnL2) revealed the distorted trigonal bipyramidal geometry (SnO2NC2). The cytotoxic activity of compounds was tested against human cancer cell lines A549, Hela, MCF7 and normal cell line L6 using MTT assay. Compound 12 (Ph2SnL2), 14 (Et2SnL3), 19 (Bu2SnL4) was found most active against tested cell lines having IC50 value 22.909–32.303 μM. Further, molecular docking study was performed for the active compounds 12, 14 and 20 at 3D space of enzymes Tyrosine kinase and EGFR kinase domain.

Effect of s–se bioisosteric exchange on affinity and intrinsic efficacy of novel n-acylhydrazone derivatives at the adenosine a2a receptor

In this work, we evaluated the conformational effect promoted by the isosteric exchange of sulfur by selenium in the heteroaromatic ring of new N-acylhydrazone (NAH) derivatives (3–8, 13, 14), analogues of the cardioactive compounds LASSBio-294 (1) and LASSBio-785 (2). NMR spectra analysis demonstrated a chemical shift variation of the iminic Csp2 of NAH S/Se-isosters, suggesting a stronger intramolecular chalcogen interaction for Se-derivatives. To investigate the pharmacological profile of these compounds at the adenosine A2A receptor (A2AR), we performed a previously validated functional binding assay. As expected for bioisosteres, the isosteric-S/Se replacement affected neither the affinity nor the intrinsic efficacy of our NAH derivatives (1–8). However, the N-methylated compounds (2, 6–8) presented a weak partial agonist profile at A2AR, contrary to the non-methylated counterparts (1, 3–5), which appeared as weak inverse agonists. Additionally, retroisosterism between aromatic rings of NAH on S/Se-isosters mimicked the effect of the N-methylation on intrinsic efficacy at A2AR, while meta-substitution in the phenyl ring of the acyl moiety did not. This study showed that the conformational effect of NAH-N-methylation and aromatic rings retroisosterism changed the intrinsic efficacy on A2AR, indicating the S/Se-chalcogen effect to drive the conformational behavior of this series of NAH.

AMINO ALCOHOL DERIVATIVE, PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF

The present invention belongs to the field of medicine, and specifically discloses an amino alcohol derivative represented by Formula I, a pharmaceutically acceptable salt, solvate, polymorph or prodrug thereof. In addition, the present invention also discloses a pharmaceutical composition comprising the above substances, and a use of the substance in the preparation of a medicament for the prevention and treatment of an immune inflammatory disease, or a disease or condition associated with immunological competence such as multiple sclerosis, ALS, CIDP, systemic lupus erythematosus, rheumatoid arthritis, ulcerative colitis, psoriasis, polymyositis, etc.

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

Mild Copper-Catalyzed Addition of Arylboronic Esters to Di- tert -butyl Dicarbonate: An Easy Access to Methyl Arylcarboxylates

An efficient copper-catalyzed addition of arylboronic esters to (Boc) 2O was developed. The reaction can be conducted under exceedingly mild conditions and is compatible with a variety of synthetically relevant functional groups. It therefore represents a useful alternative route for the synthesis of methyl arylcarboxylates. A preliminary mechanistic study indicated the involvement of an addition-elimination mechanism.

Design, synthesis and the structure-activity relationship of agonists targeting on the ALDH2 catalytic tunnel

ALDH2, a key enzyme in the alcohol metabolism process, detoxifies several kinds of toxic small molecular aldehydes, which induce severe organ damages. The development of novel Alda-1 type ALDH2 activators was mostly relied on HTS but not rational design so far. To clarify the structure–activity relationship (SAR) of the skeleton of Alda-1 analogs by synthesis of the least number of analogs, we prepared 31 Alda-1 analogs and 3 isoflavone derivatives and evaluated for their ALDH2-activating activity. Among these, the ALDH2-activating activity of mono-halogen-substituted (Cl and Br) N-piperonylbenzamides 3b and 3 k, and non-aromatic amides 8a-8c, were 1.5–2.1 folds higher than that of Alda-1 at 20 μM. The relationship between binding affinity in computer aided molecular docking model and the ALDH2-activating activity assays were clarified as follows: for Alda-1 analogs, with the formation of halogen bonds, the enzyme-activating activity was found to follow a specific regression curve within the range between ?5 kcal/mol and ?4 kcal/mol. For isoflavone derivatives, the basic moiety on the B ring enhance the activating activity. These results provide a new direction of utilizing computer-aided modeling to design novel ALDH2 agonists in the future.

ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-1" PATHWAY AND METHODS OF USE THEREOF

The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.

ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I' PATHWAY AND METHODS OF USE THEREOF

The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.

ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I" PATHWAY AND METHODS OF USE THEREOF

The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.