13720-94-0

Basic information

• Product Name: ETHYL 4-CHLORO-3-QUINOLINECARBOXYLATE
• Synonyms: 4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;AURORA 18125;ETHYL 4-CHLORO-3-QUINOLINECARBOXYLATE;ETHYL 4-CHLOROQUINOLINE-3-CARBOXYLATE;NSC 109461;NSC 136916;4-CHLORO-3-QUINOLINECARBOXYLATE
• CAS NO: 13720-94-0
• Molecular Formula: C₁₂H₁₀ClNO₂
• Molecular Weight: 235.67
• Product Categories: Acids and Derivatives;Heterocycles
• Mol File: 13720-94-0.mol

Chemical Properties

• Melting Point: 46-48°C
• Boiling Point: 328.5 °C at 760 mmHg
• Flash Point: 152.5 °C
• Appearance: /
• Density: 1.286
• Vapor Pressure: 0.000189mmHg at 25°C
• Refractive Index: 1.609
• PKA: 1.78±0.24(Predicted)
• CAS DataBase Reference: ETHYL 4-CHLORO-3-QUINOLINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-CHLORO-3-QUINOLINECARBOXYLATE(13720-94-0)
• EPA Substance Registry System: ETHYL 4-CHLORO-3-QUINOLINECARBOXYLATE(13720-94-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13720-94-0(Hazardous Substances Data)

Usage

Uses

Ethyl 4-chloroquinoline-3-carboxylate is used as organic chemical synthesis intermediate.

InChI:InChI=1/C12H10ClNO2/c1-2-16-12(15)9-7-14-10-6-4-3-5-8(10)11(9)13/h3-7H,2H2,1H3

Upstream product

• 26892-90-0 ethyl 4-hydroxy-3-quinolinecarboxylate 
• 52980-28-6 ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 54535-22-7 diethyl (anilinomethylene)malonate 
• 62-53-3 aniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 40516-46-9 diethyl (ethoxymethylene)malonate 
• 16863-96-0 3-chloro-1H-indole 
• 22736-43-2 ethyl 2-bromo-2-diazoacetate 

Downstream Products

• 23511-93-5 4-anilino-quinoline-3-carboxylic acid ethyl ester 
• 21168-46-7 4-Chlor-3-hydroxymethyl-chinolin 
• 13720-96-2 4-ethoxy-3-ethoxycarbonylquinoline 
• 77779-60-3 2-phenyl-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 77779-36-3 2-(4-chlorophenyl)-pyrazolo[4,3-c]quinolin-3-one 
• 77779-50-1 2-(p-methoxyphenyl)-pyrazolo[4,3-c]quinolin-3(5H)-one 
• 1027028-91-6 4-[N'-(2-Chloro-phenyl)-hydrazino]-quinoline-3-carboxylic acid ethyl ester 
• 77779-43-2 2-(2,4-dichlorophenyl)-pyrazolo[4,3-c]-quinolin-3(5H)-one 
• 77792-54-2 4-[N'-(2,4-Dichloro-phenyl)-hydrazino]-quinoline-3-carboxylic acid ethyl ester 
• 93074-72-7 ethyl 4-aminoquinoline-3-carboxylate 
• 50741-46-3 ethyl 3-quinolinecarboxylate 
• 26892-90-0 ethyl 4-hydroxy-3-quinolinecarboxylate 
• 77779-51-2 CGS 11361 

Relevant articles and documents

A multifunctional therapeutic approach: Synthesis, biological evaluation, crystal structure and molecular docking of diversified 1H-pyrazolo[3,4-b]pyridine derivatives against Alzheimer's disease

2-(piperazin-1-yl)–N-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamides are described as a new class of selective and potent acetylcholinesterase (AChE) inhibitors and amyloid β aggregation inhibitors. Formation of synthesized compounds (P1–P9) was justified via H1 NMR, C13 NMR, mass spectra and single crystal X-Ray diffraction study. All compounds were evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity, inhibition of self-mediated Aβ aggregation and Cu(II)-mediated Aβ aggregation. Also, docking study carried out was in concordance with in vitro results. The most potent molecule amongst the derivatives exhibited excellent anti-AChE activity (IC50 = 4.8 nM). Kinetic study of P3 suggested it to be a mixed type inhibitor. In vitro study revealed that all the compounds are capable of inhibiting self-induced β-amyloid (Aβ) aggregation with the highest inhibition percentage to be 81.65%. Potency of P1 and P3 to inhibit self-induced Aβ1-42 aggregation was ascertained by TEM analysis. Compounds were also evaluated for their Aβ disaggregation, antioxidation, metal-chelation activity.

PANICINOTAM DERIVATIVE, PREPARATION METHOD AND USE THEREOF

Provided are penicinotam derivatives, a tautomer, a stereoisomer, a racemate, a nonequal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition comprising the deriva

Sulfonamide-based 4-anilinoquinoline derivatives as novel dual Aurora kinase (AURKA/B) inhibitors: Synthesis, biological evaluation and in silico insights

Aurora kinases (AURKs) were identified as promising druggable targets for targeted cancer therapy. Aiming at the development of novel chemotype of dual AURKA/B inhibitors, herein we report the design and synthesis of three series of 4-anilinoquinoline derivatives bearing a sulfonamide moiety (5a-d, 9a-d and 11a-d). The percent inhibition of AURKA/B was determined for all target quinolines, then compounds showed more than 50percent inhibition on either of the enzymes, were evaluated further for their IC50 on the corresponding enzyme. In particular, compound 9d displayed potent AURKA/B inhibitory activities with IC50 of 0.93 and 0.09 μM, respectively. Also, 9d emerged as the most efficient anti-proliferative analogue in the US-NCI anticancer assay toward the NCI 60 cell lines panel, with broad spectrum activity against different cell lines from diverse cancer subpanels. Docking studies, confirmed that, the sulfonamide SO2 oxygen was involved in a hydrogen bond with Lys162 and Lys122 in AURKA and AURKB, respectively, whereas, the sulfonamide NH could catch hydrogen bond interaction with the surrounding amino acid residues Lys141, Glu260, and Asn261 in AURKA and Lys101, Glu177, and Asp234 in AURKB. Furthermore, N1 nitrogen of the quinoline scaffold formed an essential hydrogen bond with the hinge region key amino acids Ala213 and Ala173 in AURKA and AURKB, respectively.

Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamidesAQ3 as carbonic anhydrase isoforms I and II inhibitors

Carbonic anhydrases (CAs, EC 4.2.1.1) are crucial metalloenzymes that are involved in diverse bioprocesses. We report the synthesis and biological evaluation of novel series of benzenesulfonamides incorporating un/substituted ethyl quinoline-3-carboxylate moieties. The newly synthesised compounds were in vitro evaluated as inhibitors of the cytosolic human (h) isoforms hCA I and II. Both isoforms hCA I and II were inhibited by the quinolines reported here in variable degrees: hCA I was inhibited with KIs in the range of 0.966–9.091 μM, whereas hCA II in the range of 0.083–3.594 μM. The primary 7-chloro-6-flouro substituted sulphfonamide derivative 6e (KI = 0.083 μM) proved to be the most active quinoline in inhibiting hCA II, whereas, its secondary sulfonamide analog failed to inhibit the hCA II up to 10 μM, confirming the crucial role of the primary sulphfonamide group, as a zinc-binding group for CA inhibitory activity.

4 - Amino quinoline -3 - a ester derivative and its preparation method and application

The invention provides a 4 - substituted amino quinoline - 3 - carboxylic acid ester derivative and its preparation method and application, 4 - amino quinoline - 3 - carboxylic acid ester derivative of the general formula: . The compounds in vitro demonstrates very good anti-tumor activity, can be applied to the preparation of anti-tumor drug.

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: Novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

We present a short and efficient way of synthesizing two synthetically versatile 4-quinolone-3-carboxylate building blocks by cyclopropanation-ring expansion of 3-chloroindoles with α-halodiazoacetates as the key step. This novel transformation was applied towards the synthesis of the antibiotic drug norfloxacin.

Tetracyclic lactam compound, preparation method and application thereof

The invention relates to a tetracyclic lactam compound, or a tautomer, a stereisomer, racemate, a non-equivalent mixture of an enantiomer, a geometrical isomer, a solvate, medically acceptable salt orprodrug thereof, and a drug combination containing the same. The invention further discloses application of the tetracyclic lactam compound or the drug combination serving as drugs, particularly as antibacterial, antiviral and antiparasitic drugs.

Method for preparing penicinotam compound

The invention belongs to the field of organic synthesis and in particular relates to a method for preparing a penicinotam compound. The method comprises the following steps: by taking phenylamine andethoxy methylene propane dioic acid dio-ethylest as initial raw materials, carrying out a condensation reaction, carrying out a Gould-Jacob reaction so as to form a quinoline mother ring, further carrying out a bromo- and Suzuki reaction so as to obtain a 2-(1-(t-butyloxycarboryl)-1H-pyrrole-2-yl)-4-chloroquinoline-3-ethyl formate intermediate, and finally carrying out a ring closing reaction, thereby obtaining a target product, namely the penicinotam.

Method for preparing penicinoline compound

The invention discloses a method for preparing a penicinoline compound and belongs to the field of organic synthesis. The method comprises the following steps: by taking phenylamine and ethoxy methylene propane dioic acid dio-ethylest as initial raw materials, carrying out a condensation reaction, carrying out a Gould-Jacob reaction so as to form a quinoline mother ring, further carrying out a bromo- and Suzuki reaction so as to obtain a 2-(1-(t-butyloxycarboryl)-1H-pyrrole-2-yl)-4-chloroquinoline-3-ethyl formate intermediate, and finally carrying out hydrolysism obtaining penicinoline.

Panicinotam analog and preparation method and use thereof

The present invention relates to a panicinotam analog, or a tautomer, a stereoisomer, a raceme, a non-equivalent mixture of enantiomers, a geometrical isomer, a solvate, a pharmaceutically-acceptablesalt or a prodrug thereof, and a pharmaceutical composition comprising the panicinotam analog. The present invention also provides use of the panicinotam analog or the pharmaceutical composition serving as drugs, and especially as antivirus, antibacterial and antiparasitic drugs.