17394-77-3

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate is used as a precursor in the synthesis of pharmaceuticals for its ability to undergo various chemical reactions, such as nucleophilic addition and reduction. This allows for the creation of a wide range of biologically active compounds, making it a valuable component in drug development.
Used in Organic Synthesis:
In the field of organic synthesis, diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate is used as a versatile building block for the synthesis of various organic compounds. Its unique structure, featuring an anilino group, a methylenedioxy bridge, and a malonate ester, enables it to participate in a variety of chemical reactions, contributing to the creation of diverse organic molecules.
Used in Fine Chemical Production:
Diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate is also used as an important intermediate in the production of fine chemical products. Its presence in the synthesis process allows for the development of high-quality specialty chemicals that are utilized in various industries, such as fragrances, dyes, and other specialty applications.

InChI:InChI=1/C15H17NO6/c1-3-19-14(17)11(15(18)20-4-2)8-16-10-5-6-12-13(7-10)22-9-21-12/h5-8,16H,3-4,9H2,1-2H3

Upstream product

• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 105-53-3 diethyl malonate 

Downstream Products

• 14205-65-3 ethyl 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylate 
• 59134-89-3 8-chloro-2H-[1,3]dioxolo[4,5-g]quinoline 
• 86749-73-7 6,7-methylenedioxy-4-phenoxyquinoline 
• 26893-27-6 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid 
• 26893-17-4 ethyl 8-chloro-[1,3]dioxolo[4,5-g]quinoline-7- carboxylate 

Relevant academic research and scientific papers

Optimization of activity localization of quinoline derivatives: Design, synthesis, and dual evaluation of biological activity for potential antitumor and antibacterial agents

A novel of quarternary amine around a quinolinium iodide combined with even number alkyl chain were prepared in a several step in moderate yield starting from malonic ester and benzo[d][1,3]dioxol-5-amine. All of the active structure compounds were identified by nuclear magnetic resonance (NMR), such as 1H NMR, 13C NMR, infrared radiation (IR), high resolution mass spectrometry (HR-MS) and Carlo Erba Instruments CHNS-O EA1108 spectra analysis. With regard to the anticancer properties, the in vitro cytotoxicity against three human cancer cell lines (A-549, Hela and SGC-7901) were evaluated. The antibacterial properties against two human bacterial strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target compounds, 5–12, exhibited significant antitumor and antibacterial activity, of which compound 12 was found to be the most potent derivative with IC50 values of 5.18 ± 0.64, 7.62 ± 1.05, 17.59 ± 0.41, and 54.45 ± 4.88 against A-549, Hela, SGC-7901, and L-02 cells, respectively, stronger than the positive control 5-FU and MTX. Furthermore, compound 12 had the most potent inhibitory activity. The MIC of this compound against Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739) was 3.125 nmol·mL?1, which was smaller than that of the reference agents, amoxicillin and ciprofloxacin.

Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents

A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A-549, HeLa and SGC-7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8-((4-(benzyloxy)phenyl)amino)-7-(ethoxycarbonyl)-5-propyl-[1,3]dioxolo[4,5-g]quinolin-5-ium (12) was found to be the most potent derivative with IC50 values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A-549, HeLa, SGC-7901, and L-02 cells, respectively, stronger than the positive controls 5-FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ? mL?1, which was smaller than that against the reference agents amoxicillin and ciprofloxacin.

Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay

Type-1 ryanodine receptor (RyR1) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyR1 are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyR1 causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyR1 channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyR1 channel inhibitors.

METHODS FOR TREATING HEMATOLOGICAL MALIGNANCIES

The invention provides methods and pharmaceutical compositions for treating certain hematological cancers