81581-27-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester is used as a synthetic intermediate for the production of pharmaceuticals and other organic compounds. Its unique chemical structure allows it to be a valuable building block in the synthesis of more complex molecules with potential therapeutic properties.
Used in Research and Development:
In academic and industrial laboratories, 3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester is used for research and development purposes. Its potential applications in the pharmaceutical industry make it an essential compound for exploring new drug candidates and understanding its therapeutic properties.
Used in Organic Synthesis Reactions:
Due to its chemical structure, 3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester is used in various organic synthesis reactions. Its dioxolane ring and propionic acid moiety make it a versatile compound for creating new organic compounds with potential applications in different industries.

InChI:InChI=1/C12H12O5/c1-2-15-12(14)6-9(13)8-3-4-10-11(5-8)17-7-16-10/h3-5H,2,6-7H2,1H3

Upstream product

• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 141-78-6 ethyl acetate 
• 81581-26-2 3,4-Methylendioxybenzoyl-acetessigsaeure-ethylester 
• 94-53-1 Piperonylic acid 
• 37517-78-5 magnesium bis(3-ethoxy-3-oxopropanoate) 
• 623-73-4 diazoacetic acid ethyl ester 
• 120-57-0 piperonal 
• 34023-63-7 ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-hydroxypropanoate 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 105-58-8 Diethyl carbonate 
• 6148-64-7 ethyl potassium malonate 
• 135696-67-2 piperomylimidazole 

Downstream Products

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 112333-50-3 7-(4-methoxyphenyl)-6-(3,4-methylenedioxyphenyl)-1,2,3,4,6,9,9a-octahydroquinolizine 
• 133-03-9 2-exo,6-exo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 112778-68-4 (6R,7S,8R)-5-Oxo-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid diethyl ester 
• 1404446-64-5 5-(benzo[d][1,3]dioxol-5-yl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404446-62-3 5-(benzo[d][1,3]dioxol-5-yl)-3-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-02-4 3-(4-chlorobenzyl)-5-(benzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-01-3 3-(3-chlorobenzyl)-5-(benzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 

Relevant academic research and scientific papers

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.

Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’-Keto-β-Amino Esters via Dynamic Kinetic Resolution

An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti β’-hydroxy-β-amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100). (Figure presented.).

An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot

A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.

Design, Synthesis, and Biochemical Characterization of Non-Native Antagonists of the Pseudomonas aeruginosa Quorum Sensing Receptor LasR with Nanomolar IC50 Values

Quorum sensing (QS), a bacterial cell-to-cell communication system mediated by small molecules and peptides, has received significant interest as a potential target to block infection. The common pathogen Pseudomonas aeruginosa uses QS to regulate many of its virulence phenotypes at high cell densities, and the LasR QS receptor plays a critical role in this process. Small molecule tools that inhibit LasR activity would serve to illuminate its role in P. aeruginosa virulence, but we currently lack highly potent and selective LasR antagonists, despite considerable research in this area. V-06-018, an abiotic small molecule discovered in a high-throughput screen, represents one of the most potent known LasR antagonists but has seen little study since its initial report. Herein, we report a systematic study of the structure-activity relationships (SARs) that govern LasR antagonism by V-06-018. We synthesized a focused library of V-06-018 derivatives and evaluated the library for bioactivity using a variety of cell-based LasR reporter systems. The SAR trends revealed by these experiments allowed us to design probes with 10-fold greater potency than that of V-06-018 and 100-fold greater potency than other commonly used N-acyl-l-homoserine lactone (AHL)-based LasR antagonists, along with high selectivities for LasR. Biochemical experiments to probe the mechanism of antagonism by V-06-018 and its analogues support these compounds interacting with the native ligand-binding site in LasR and, at least in part, stabilizing an inactive form of the protein. The compounds described herein are the most potent and efficacious antagonists of LasR known and represent robust probes both for characterizing the mechanisms of LuxR-type QS and for chemical biology research in general in the growing QS field.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Quinoline derivative VCTb9 and application thereof in preparation of anticancer drugs

The invention belongs to the field of new drugs, and particularly relates to a quinoline derivative VCTb9 and application thereof in preparation of anticancer drugs. During synthesis of quinoline derivatives, the quinoline derivative with high anticancer activity is found. The quinoline derivative also has excellent inhibition effects on lung carcinoma cells, breast cancer cells and gastric carcinoma cells, is suitable for being developed into new drugs for inhibiting growth of the cancer cells and has broad application prospects.

Quinoline derivative VCTb5 and application thereof in preparation of anticancer drugs

The invention belongs to the field of new drugs, and particularly relates to a quinoline derivative and application thereof in preparation of anticancer drugs. In the process of synthesizing the quinoline derivative, it is found that the quinoline derivative has a substance high in anticancer activity. Moreover, compared with tumor cells, the derivative has a good inhibiting effect on lung cancercells, breast cancer cells and gastric cancer cells, is suitable for being developed into new drugs for inhibiting cancer cell growth, and has wide application prospects.

Targeting tubulin polymerization by novel 7-aryl-pyrroloquinolinones: Synthesis, biological activity and SARs

Earlier studies had confirmed that the 7-phenylpyrroloquinolinone (7-PPyQ) nucleus was an important scaffold for new chemotherapeutic drugs targeting microtubules. For wide-ranging SARs, a series of derivatives were synthesized through a robust procedure. For comparison with the reference 3-ethyl-7-PPyQ 31, the angular geometry and substituents at the 3 and 7 positions were varied to explore interactions inside the colchicine site of tubulin. Of the new compounds synthesized, potent cytotoxicity (low and sub-nanomolar GI50 values) was observed with 21 and 24, both more potent than 31, in both leukemic and solid tumor cell lines. Neither compound 21 nor 24 induced significant cell death in normal human lymphocytes, suggesting that the compounds may be selectively active against cancer cells. In particular, 24 was a potent inducer of apoptosis in the A549 and HeLa cell lines. With both compounds, induction of apoptosis was associated with dissipation of the mitochondrial transmembrane potential and production of reactive oxygen species, indicating that cells treated with the compounds followed the intrinsic pathway of apoptosis. Moreover, immunoblot analysis revealed that compound 24 even at 50 nM reduced the expression of anti-apoptotic proteins such as Bcl-2 and Mcl-1. Finally, molecular docking studies of the newly synthesized compounds demonstrate that active pyrroloquinolinone derivatives strongly bind in the colchicine site of β-tubulin.

Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes

A method for the regioselective synthesis of a wide range of dihydrothiophenes was developed from the rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes. Tandem rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation was also demonstrated for the one-pot regioselective synthesis of various thiophenes. Advantages of the present method include a broad substrate scope, wide functional group compatibility, and high regioselectivity.