50593-73-2

Basic information

• Product Name: 4-CHLORO-6-METHOXY-2-METHYLQUINOLINE
• Synonyms: TIMTEC-BB SBB010126;4-CHLORO-6-METHOXYQUINALDINE;4-CHLORO-6-METHOXY-2-METHYLQUINOLINE;6-Methoxy-4-chloro-2-methylquinoline;6-Methoxy-4-chloroquinalidine;6-Methoxy-4-chloro quinilidine;4-Chloro-6-methoxy-2-methyl-1-azanaphthalene;4-Chloro-6-Methoxy-2-Methylquinoline 4-Chloro-6-Methoxy-2-Methyl-Quinoline
• CAS NO: 50593-73-2
• Molecular Formula: C₁₁H₁₀ClNO
• Molecular Weight: 207.66
• Mol File: 50593-73-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 308.8 °C at 760 mmHg
• Flash Point: 140.6 °C
• Appearance: /
• Density: 1.228 g/cm³
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 4-CHLORO-6-METHOXY-2-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-METHOXY-2-METHYLQUINOLINE(50593-73-2)
• EPA Substance Registry System: 4-CHLORO-6-METHOXY-2-METHYLQUINOLINE(50593-73-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36/37/39-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 50593-73-2(Hazardous Substances Data)

Usage

General Description

4-Chloro-6-methoxy-2-methylquinoline is a chemical compound with the molecular formula C11H10ClNO. It is a quinoline derivative with a chlorine atom at the 4th position, a methoxy group at the 6th position, and a methyl group at the 2nd position on the quinoline ring. 4-CHLORO-6-METHOXY-2-METHYLQUINOLINE has potential applications in the pharmaceutical industry, where it may be used as a building block for the synthesis of various drugs and biologically active molecules. Its unique structure and functional groups make it a valuable intermediate for the production of pharmaceuticals and other organic compounds. Additionally, it may also possess biological activities that make it a target for further research in medicinal chemistry.

InChI:InChI=1/C11H10ClNO/c1-7-5-10(12)9-6-8(14-2)3-4-11(9)13-7/h3-6H,1-2H3

Upstream product

• 80056-93-5 ethyl 3-[(4-methoxyphenyl)imino]butanoate 
• 33240-23-2 ethyl 3-((4-methoxyphenyl)amino)but-2-enoate 
• 104-94-9 4-methoxy-aniline 
• 58596-37-5 6-methoxy-2-methylquinolin-4(1H)-one 
• 15644-90-3 6-methoxy-2-methylquinolin-4-ol 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 657367-83-4 N-(4-aminophenyl)-6-methoxy-2-methylquinolin-4-amine 
• 1171611-95-2 4-hydrazino-6-methoxy-2-methylquinoline hydrochloride 
• 29125-41-5 6-methoxy-2-methyl-4-(2-(pyridin-3-ylmethylene)hydrazinyl)quinoline 

Relevant articles and documents

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Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines

There is an urgent need to develop new efficacious antimalarials to address the emerging drug-resistant clinical cases. Our previous phenotypic screening identified styrylquinoline UCF501 as a promising antimalarial compound. To optimize UCF501, we herein report a detailed structure-activity relationship study of 2-arylvinylquinolines, leading to the discovery of potent, low nanomolar antiplasmodial compounds against a Plasmodium falciparum CQ-resistant Dd2 strain, with excellent selectivity profiles (resistance index 200). Several metabolically stable 2-arylvinylquinolines are identified as fast-acting agents that kill asexual blood-stage parasites at the trophozoite phase, and the most promising compound 24 also demonstrates transmission blocking potential. Additionally, the monophosphate salt of 24 exhibits excellent in vivo antimalarial efficacy in the murine model without noticeable toxicity. Thus, the 2-arylvinylquinolines represent a promising class of antimalarial drug leads.

ANTIMALARIAL COMPOUNDS

Antimalarial compounds of the formula: in which n is 1 or 2; X is C or N; R1 is a moiety comprising a secondary amine and a tertiary amine joined by a C2 to C4 alkyl chain; and R2 is CF3, F, or H, or an analog, combination, derivative, prodrug, stereoisomer, or pharmaceutically acceptable salt thereof. Pharmaceutical compounds including the antimalarial compounds. Methods of treating or preventing malaria comprising administering an effective amount of the antimalarial compounds.

Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription

Aberrant overexpression of heterogeneous nuclear ribonucleoprotein K (hnRNP K) is a key feature in oncogenesis and progression of many human cancers. hnRNP K has been found to be a transcriptional activator to up-regulate c-myc gene transcription, a critical proto-oncogene for regulation of cell growth and differentiation. Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound 25) was determined to be the first-reported hnRNP K binding ligand with its KD values of 4.6 and 2.6 μM measured with SPR and MST, respectively. Subsequent evaluation showed that the binding of compound 25 to hnRNP K could disrupt its unfolding of c-myc promoter i-motif, resulting in down-regulation of c-myc transcription. Compound 25 showed a selective anti-proliferative effect on human cancer cell lines with IC50 values ranged from 1.36 to 3.59 μM. Compound 25 exhibited good tumor growth inhibition in a Hela xenograft tumor model, which might be related to its binding with hnRNP K. These findings illustrated that inhibition of DNA-binding protein hnRNP K by compound 25 could be a new and selective strategy of regulating oncogene transcription instead of targeting promoter DNA secondary structures such as G-quadruplexes or i-motifs.