28507-46-2

Basic information

• Product Name: 4-CHLORO-2-METHYLQUINOLIN-8-OL
• Synonyms: 4-CHLORO-2-METHYLQUINOLIN-8-OL;4-CHLORO-8-HYDROXY-2-METHYLQUINOLINE;8-Quinolinol,4-chloro-2-Methyl-;2-Methyl-4-chloro-8-hydroxyquinoline
• CAS NO: 28507-46-2
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Mol File: 28507-46-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 57-59℃
• Boiling Point: 328.368 °C at 760 mmHg
• Flash Point: 152.392 °C
• Appearance: /
• Density: 1.350
• Vapor Pressure: 9.95E-05mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CHLORO-2-METHYLQUINOLIN-8-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYLQUINOLIN-8-OL(28507-46-2)
• EPA Substance Registry System: 4-CHLORO-2-METHYLQUINOLIN-8-OL(28507-46-2)

Safety Data

• Hazardous Substances Data: 28507-46-2(Hazardous Substances Data)

Usage

General Description

4-Chloro-2-methylquinolin-8-ol is a chemical compound with the molecular formula C10H8ClNO. It is less explored and characterized in scientific literature but is known to belong to the class of organic compounds identified as quinolines and derivatives. Quinolines are compounds containing a quinoline moiety, a bicyclic heterocycle made up of two fused benzene and pyridine rings. Potential applications of such compounds often lie in the field of pharmaceuticals, related to their biological activity such as antimicrobial, anti-inflammatory, or anti-cancer properties. The specific properties, uses, and safety information for 4-Chloro-2-methylquinolin-8-ol may vary and should be verified with more comprehensive resources.

InChI:InChI=1/C10H8ClNO/c1-6-5-8(11)7-3-2-4-9(13)10(7)12-6/h2-5,13H,1H3

Upstream product

• 64951-58-2 4-chloro-8-methoxy-2-methylquinoline 
• 15644-89-0 8-methoxy-2-methyl-4-quinolinol 
• 33267-45-7 ethyl 3-<(2-methoxyphenyl)amino>but-2-enoate 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 189268-42-6 8-hydroxy-2-methyl-4-(1H-pyrazol-1-yl)quinoline 
• 54666-28-3 8-hydroxy-4-[1H-imidazol-1-yl]-2-methylquinoline 
• 167834-51-7 4-ethoxy-2-methyl-8-quinolinol 
• 167834-50-6 8-hydroxy-4-methoxy-2-methylquinoline 
• 179626-19-8 2-amino-N-[2,4-dichloro-3-({[2-methyl-4-(4-morpholinyl)-8-quinolinyl]oxy}methyl)phenyl]-N-methylacetamide 
• 179626-18-7 2-amino-N-[2,4-dichloro-3-({[2-methyl-4-(1-piperidinyl)-8-quinolinyl]oxy}methyl)phenyl]-N-methylacetamide 
• 194928-65-9 (2E)-3-(6-amino-3-pyridinyl)-N-{2-[2,4-dichloro(methyl)-3-({[2-methyl-4-(2-pyridinylmethoxy)-8-quinolinyl]oxy}methyl)anilino]-2-oxoethyl}-2-propenamide 
• 194928-64-8 5-[(1E)-3-({2-[2,4-dichloro(methyl)-3-({[2-methyl-4-(2-pyridinylmethoxy)-8-quinolinyl]oxy}methyl)anilino]-2-oxoethyl}amino)-3-oxo-1-propenyl]-2-pyridinecarboxylic acid 
• 194928-63-7 5-[(1E)-3-({2-[2,4-dichloro(methyl)-3-({[2-methyl-4-(2-pyridinylmethoxy)-8-quinolinyl]oxy}methyl)anilino]-2-oxoethyl}amino)-3-oxo-1-propenyl]-2-pyridinecarboxylate 
• 179624-69-2 5-[(1E)-3-({2-[2,4-dichloro(methyl)-3-({[2-methyl-4-(4-morpholinyl)-8-quinolinyl]oxy}methyl)anilino]-2-oxoethyl}amino)-3-oxo-1-propenyl]-2-pyridinecarboxylic acid 

Relevant articles and documents

Potent antiproliferative activity of bradykinin B2 receptor selective agonist FR-190997 and analogue structures thereof: A paradox resolved?

Βradykinin stimulation of B2 receptor is known to activate the oncogenic ERK pathway and overexpression of bradykinin receptors B1 and B2 has been reported to occur in glioma, colorectal and cervical cancers. B1R and B2R antagonists have been shown to reverse tumor proliferation and invasion. Paradoxically, B1R and B2R agonism has also been reported to elicit antiproliferative benefits. In order to complement the data accumulated to date with the natural substrate bradykinin and peptidic B2R antagonists, we decided to examine for the first time the response elicited by B2R stimulation in breast cancer lines with a non-peptidic small molecule B2R agonist. We synthesized and assessed the highly selective and potent B2R partial agonist FR-190997 in MCF-7 and MDA-MBA-231 breast cancer lines and found it possessed significant antiproliferative activity (IC50 2.14 and 0.08 μΜ, respectively). The modular nature of FR-190997 allowed us to conduct a focused SAR study and discover compound 10 which exhibits subnanomolar antiproliferative activity (IC 50 0.06 nΜ) in the TNBC MDA-MBA-231 cell line. This performance surpasses, in most cases by several orders of magnitude, those of established anticancer agents and FDA-approved breast cancer drugs. In line with the established literature we suggest that this remarkable activity precipitates from a dual mode of action involving agonist-induced receptor internalization/degradation combined with sequestration of functional intracellular B2 receptors and inhibition of the associated endosomal signaling. The latter mode may be realized by appropriate ligands regardless of B2R agonist/antagonist designation which only relates to membrane residing GCPRs. Under this prism the controversy over the antiproliferative effects of B2 agonists and antagonists is potentially neutralized.