41037-28-9

Basic information

• Product Name: 6-Bromo-4-methylquinoline
• Synonyms: 6-bromo-4-methylquinoline;Quinoline, 6-broMo-4-Methyl-
• CAS NO: 41037-28-9
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08
• Mol File: 41037-28-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 94-95℃
• Boiling Point: 315.773 °C at 760 mmHg
• Flash Point: 144.774 °C
• Appearance: /
• Density: 1.488 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.85±0.16(Predicted)
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: 6-Bromo-4-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-4-methylquinoline(41037-28-9)
• EPA Substance Registry System: 6-Bromo-4-methylquinoline(41037-28-9)

Safety Data

• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 41037-28-9(Hazardous Substances Data)

Usage

Description

6-Bromo-4-methylquinoline is an organic compound characterized by its quinoline structure with a bromine atom at the 6th position and a methyl group at the 4th position. It is a synthetic intermediate used in the chemical industry for the production of various compounds.

Uses

Used in Pharmaceutical Industry:
6-Bromo-4-methylquinoline is used as a reagent for the synthesis of dibenzenesulfonamide derivatives, which are important compounds in the pharmaceutical industry. These derivatives have potential applications in the development of new drugs due to their diverse chemical properties and biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 6-Bromo-4-methylquinoline serves as a key intermediate for the production of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of complex molecules with specific properties and applications.

InChI:InChI=1/C10H8BrN/c1-7-4-5-12-10-3-2-8(11)6-9(7)10/h2-6H,1H3

Upstream product

• 78-94-4 methyl vinyl ketone 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 7101-68-0 4-methyl-6-quinolinecrboxylic acid 
• 916812-60-7 6-formyl-4-methylquinoline 
• 476474-52-9 6-bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline 
• 898391-75-8 6-bromoquinoline-4-carbaldehyde 
• 109555-19-3 4-[trans-2-(6-bromo-[4]quinolyl)-vinyl]-N,N-dimethyl-aniline 

Relevant articles and documents

Structural optimization towards promising β-methyl-4-acrylamido quinoline derivatives as PI3K/mTOR dual inhibitors for anti-cancer therapy: The in vitro and in vivo biological evaluation

Built upon the 4-acrylamido quinoline derivative 4, a previously discovered PI3K/mTOR dual inhibitor, structural modification was undertaken in this study with the attempt to improve its oral exposure via introducing steric hindrance to the 4-acrylamido functionality. Consequently, 14d, as the representative among the synthesized compounds, exhibited IC50 values of 0.80, 0.67, 1.30, 1.30 and 5.0 nM against PI3Kα, PI3Kβ, PI3Kγ, PI3Kδ and mTOR, respectively. Besides, 14d displayed comparable anti-proliferative activity against both PC3 and U87MG cell lines to that of the positive reference GSK2126458 with respective GI50 value of 0.36 and 0.14 μM. Kinase selectivity assay showed that 14d was selective to PI3K family. In U87MG cells, 14d can strongly down-regulate PI3K/Akt/mTOR pathway via blocking both PI3K and mTOR signaling at the concentration as low as 25 nM. Importantly, following a PO dose of 5 mg/kg in male SD rats, 14d displayed favorable oral exposure (AUC0-t = 1336.16 h × ng/mL, AUC0-∞ = 1447.63 h × ng/mL) and high maximum plasma concentration (Cmax = 903.00 ng/mL). In a U87MG glioblastoma xenograft model, tumor growth inhibition of 93.5% and tumor regression were observed at PO dose of 30 and 60 mg/kg, respectively. Meanwhile, no overt loss of body weight was observed in the 14d-treated groups. Taken together, 14d, by virtue of its attractive performance, merits further development as a potential anti-tumor candidate.

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

NOVEL PYRAZOLOPYRIDINE DERIVATIVES AS PHARMACEUTICAL AGENTS

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