70032-30-3

Basic information

• Product Name: diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate
• Synonyms: diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate;DIETHYL((3-CHLORO-4-FLUOROANILINO)METHYLENE)MALONATE;[[(3-Chloro-4-fluorophenyl)amino]methylene]propanedioic acid diethyl ester;DIETHYL 2-((3-CHLORO-4-FLUOROANILINO)METHYLENE)MALONATE(WXG01223);DIETHYL 2-((3-CHLORO-4-FLUOROANILINO)METHYLENE)MALONATE
• CAS NO: 70032-30-3
• Molecular Formula: C₁₄H₁₅ClFNO₄
• Molecular Weight: 315.7246032
• EINECS: 274-287-8
• Mol File: 70032-30-3.mol
• Article Data: 30

Chemical Properties

• Melting Point: 77-79 °C
• Boiling Point: 359.2°C at 760 mmHg
• Flash Point: 171°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 2.42E-05mmHg at 25°C
• Refractive Index: 1.548
• PKA: -1.50±0.70(Predicted)
• CAS DataBase Reference: diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate(70032-30-3)
• EPA Substance Registry System: diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate(70032-30-3)

Safety Data

• Hazardous Substances Data: 70032-30-3(Hazardous Substances Data)

Usage

Uses

Diethyl 2-(((3-Chloro-4-fluorophenyl)amino)methylene)malonate is an intermediate in the preparation of fluoroquinolone-triazole hybrid compounds with antibacterial and antifungal properties.

InChI:InChI=1/C14H15ClFNO4/c1-3-20-13(18)10(14(19)21-4-2)8-17-9-5-6-12(16)11(15)7-9/h5-8,17H,3-4H2,1-2H3

Upstream product

• 105-53-3 diethyl malonate 
• 27971-92-2 diethyl 2,2,2-trichloroethylidenepropanedioate 
• 226881-97-6 2-[2,2,2-trichloro-1-(3-chloro-4-fluoro-phenylamino)-ethyl]-malonic acid diethyl ester 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 70458-93-4 7-Chloro-6-fluoro-4-hydroxy-3-quinolinecarboxylic acid ethyl ester 
• 1435910-87-4 ethyl 7-chloro-6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant articles and documents

Microwave assisted synthesis and antibacterial activity of new quinolone derivatives

A series of novel 6-fluoro-7-(5-alkyl-1,3,4-thiadiazol/oxadiazol-2-ylsulfanyl)-4-quino-lone-3- carboxylic acids were synthesized using microwave irradiation. The compounds were tested for their in vitro antibacterial activity. All compounds containing the 1,3,4-thiadiazole/oxadiazole moiety at position 7 showed promising antibacterial activity.

NEXT-GENERATION MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.

3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities

Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate with a low IC50 value of about 2.20 ± 0.14 and was selected for further exploration. Spectroscopic analyses and agarose-gel electrophoresis assays indicated that 5a could interact with DNA and strongly inhibit topoisomerase I (Topo I). Further screening of the Topo I activity of compounds 5b, 5c, 5e, 5f, 5h, 5i, 5j, 5l, and 5n suggested that some of the compounds might exert quite a different cytotoxicity profile to that of 5a. Molecular modeling studies confirmed that 5a adopts a unique mode to interact with DNA and Topo I. Other molecular mechanistic studies suggested that the treatment of MGC-803 cells with 5a induces S phase arrest, up-regulates the pro-apoptotic protein, down-regulates the anti-apoptotic protein, activates caspase-3, and subsequently induces mitochondrial dysfunction so as to induce cell apoptosis. The in vivo efficiency of 5a was also evaluated on MGC-803 xenograft nude mice and the relative tumor growth inhibition was 42.4percent at 12 mg kg-1 without an obvious loss in the body weight. This journal is

Fluorine walk: The impact of fluorine in quinolone amides on their activity against African sleeping sickness

Human African Trypanosomiasis, also known as African sleeping sickness, is caused by the parasitic protozoa of the genus Trypanosoma. If there is no pharmacological intervention, the parasites can cross the blood-brain barrier (BBB), inevitably leading to death of the patients. Previous investigation identified the quinolone amide GHQ168 as a promising lead compound having a nanomolar activity against T. b. brucei. Here, the role of a fluorine substitution at different positions was investigated in regard to toxicity, pharmacokinetics, and antitrypanosomal activity. This ‘fluorine walk’ led to new compounds with improved metabolic stability and consistent activity against T. b. brucei. The ability of the new quinolone amides to cross the BBB was confirmed using an 18F-labelled quinolone amide derivative by means of ex vivo autoradiography of a murine brain.