84736-28-7

Usage

Uses

Used in Medicinal Chemistry:
(3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid is used as a building block or intermediate in the synthesis of pharmaceutical compounds due to its unique structural features and functional groups. Its presence of the 1,3-benzodioxol-5-yl and methoxycarbonyl groups may contribute to the compound's ability to form specific interactions with biological targets, making it a promising candidate for drug development.
Used in Drug Development:
In the pharmaceutical industry, (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid may be utilized as a precursor or key component in the creation of new drugs. Its structural complexity and the presence of the double bond in the (3Z) configuration could be leveraged to design molecules with specific biological activities, potentially leading to the development of novel therapeutic agents.
Further research and analysis of (3Z)-4-(1,3-benzodioxol-5-yl)-3-(methoxycarbonyl)but-3-enoic acid are necessary to fully understand its potential applications and benefits in the fields of medicinal chemistry and drug development. Its unique structural features and functional groups may offer new avenues for the treatment of various diseases and conditions.

Upstream product

• 120-57-0 piperonal 
• 106-65-0 Dimethyl succinate 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 124-41-4 sodium methylate 
• 123-25-1 succinic acid diethyl ester 

Downstream Products

• 84755-36-2 2-(4-benzyloxy-3-methyoxybenzyl)-3-(3,4-methylenedioxybenzyl)-γ-butyrolactone 
• 28115-68-6 (+/-)-pluviatolide 
• 17187-79-0 (E)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzylidene)dihydrofuran-2(3H)-one 
• 108146-55-0 (E)-3-(3,4,5-trimethoxybenzylidene)-4-((benzo-[d][1,3]dioxol-5-yl)methyl)dihydrofuran-2(3H)-one 
• 17187-78-9 (R)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 17187-78-9 (S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 72690-16-5 (3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Design, synthesis, and in vitro antiplatelet aggregation activities of taiwanin C

Total synthesis of taiwanin C was realised efficiently in a global yield of 52%. Taiwanin C in aggregation assays inhibited platelet aggregation in a concentration-dependent manner with an IC50 of 0.46 μM after exposure of human platelet to AA. Similarly, to AA, taiwanin C inhibited significantly TRAP-6-induced platelet aggregation with IC50 of 0.56 μM. Molecular docking studies were carried out using the molecular target the COX-1, COX-2 and PAR-1 proteins. These studies suggest that taiwanin inhibits COX-1 more strongly than COX-2. Taiwanin C showed better antiplatelet action in the presence of TRAP-6 than indomethacin and molecular docking studies suggest different mechanisms of action for the two compounds on PAR-1. These results demonstrate that taiwanin C acts very efficiently in two different signaling pathways of platelet aggregation. Although preliminary, these results indicate that taiwanin C has potential for further studies on its use for the development of new antiplatelet.

Affinity-Driven Covalent Modulator of the Glyceraldehyde-3-Phosphate Dehydrogenase (GAPDH) Cascade

Traditional medicines provide a fertile ground to explore potent lead compounds, yet their transformation into modern drugs is fraught with challenges in deciphering the target that is mechanistically valid for its biological activity. Herein we reveal that (Z)-(+)-isochaihulactone (1) exhibited significant inhibition against multiple-drug-resistant (MDR) cancer cell lines and mice xenografts. NMR spectroscopy showed that 1 resisted an off-target thiolate, thus indicating that 1 was a target covalent inhibitor (TCI). By identifying the pharmacophore of 1 (α,β-unsaturated moiety), a probe derived from 1 was designed and synthesized for TCI-oriented activity-based proteome profiling. By MS/MS and computer-guided molecular biology approaches, an affinity-driven Michael addition of the noncatalytic C247 residue of GAPDH was found to control the “ON/OFF” switch of apoptosis through non-canonically nuclear GAPDH translocation, which bypasses the common apoptosis-resistant route of MDR cancers.

Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders

Analogues of the natural product (-)-arctigenin, an activator of adenosine monophosphate activated protein kinase, were prepared in order to evaluate their effects on 2-deoxyglucose uptake in L6 myotubes and possible use in ameliorating metabolic disorders. Racemic arctigenin 2a was found to display a similar uptake enhancement as does (-)-arctigenin. As a result, the SAR study was conducted utilizing racemic compounds. The structure-activity relationship study led to the discovery of key substitution patterns on the lactone motif that govern 2-deoxyglucose uptake activities. The results show that replacement of the para-hydroxyl group of the C-2 benzyl moiety of arctigenin by Cl has a pronounced effect on uptake activity. Specifically, analogue 2p, which contains the p-Cl substituent, stimulates glucose uptake and fatty acid oxidation in L6 myotubes.

SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS-I. APPLICATION DE LA REACTION D'ULLMANN A LA SYNTHESE DE BIARYLES PRECURSEURS DE LIGNANES BISBENZOCYCLOOCTADIENES

Several biaryls bearing various substituents on both rings were synthesized in a preparativ fashion, and in yields up to 88percent by a technical improvement on the classical Ullmann reaction.All these biaryls bear reactive functional groups (i.e. formyl, methoxycarbonyl, dimethoxycarbonylpropyl and butanolidylmethyl) in both the o and o' positions.The biaryls 9, 13, 21 and 26-33 are plausible synthons for bisbenzocyclooctadiene lignans such as schizandrin and steganacin.