17394-77-3

Basic information

• Product Name: diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate
• Synonyms: diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate;2-[(1,3-Benzodioxol-5-yl)aminomethylene]malonic acid diethyl ester;diethyl [(1,3-benzodioxol-5-ylamino)methylidene]propanedioate
• CAS NO: 17394-77-3
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.29858
• EINECS: 241-421-1
• Mol File: 17394-77-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 381°Cat760mmHg
• Flash Point: 184.2°C
• Appearance: /
• Density: 1.302g/cm³
• Vapor Pressure: 5.22E-06mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate(17394-77-3)
• EPA Substance Registry System: diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate(17394-77-3)

Safety Data

• Hazardous Substances Data: 17394-77-3(Hazardous Substances Data)

Usage

General Description

Diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate is a chemical compound with the molecular formula C16H17NO5. It is a yellow solid substance that is used in organic synthesis and medicinal chemistry. diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate possesses an anilino group, a methylenedioxy bridge, and a malonate ester, making it a versatile building block for the synthesis of various biologically active compounds. It is commonly used as a precursor in the synthesis of pharmaceuticals and other organic compounds due to its ability to undergo various chemical reactions, such as nucleophilic addition and reduction. Diethyl [[3,4-(methylenedioxy)anilino]methylene]malonate is an important intermediate in the production of drugs and other fine chemical products.

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

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

Downstream Products

• 14205-65-3 ethyl 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylate 
• 26893-17-4 ethyl 8-chloro-[1,3]dioxolo[4,5-g]quinoline-7- carboxylate 
• 16171-98-5 3-ethoxycarbonyl-6,7-methylenedioxy-4-quinolone 
• 529488-53-7 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(t-butyldimethylsilanyloxy)ethyl]-2-iodo-4,5-dimethoxybenzamide 

Relevant articles and documents

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.

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.

NOTES ON THE SYNTHESIS OF 4-AMINO-6,7-DI-SEC-BUTOXYQUINOLINE, -6,7-METHYLENE-DIOXYQUINOLINE AND ITS N-ALKYLAMINOACETYL DERIVATIVES (SHORT COMMUNICATION)

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