19840-99-4

Basic information

• Product Name: CARBOSTYRIL 124
• Synonyms: 7-amino-4-methyl-2(1h)-quinolinon;7-AMINO-4-METHYL-2(1H)-QUINOLINONE;7-AMINO-2-HYDROXY-4-METHYLQUINOLINE;CARBOSTYRIL 7;CARBOSTYRIL 124;7-amino-4-methyl-2-quinolone;CARBOSTYRIL 124 99%;7-amino-4-methylquinolin-2(1H)-one
• CAS NO: 19840-99-4
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 243-363-2
• Product Categories: Quinolines, Quinazolines and derivatives;Chemical Amines;Amines;Aromatics;Heterocycles
• Mol File: 19840-99-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: >275°C (dec.)
• Boiling Point: 417.6 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: off-white to tan solid
• Density: 1.223 g/cm³
• Vapor Pressure: 3.5E-07mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.45±0.70(Predicted)
• CAS DataBase Reference: CARBOSTYRIL 124(CAS DataBase Reference)
• NIST Chemistry Reference: CARBOSTYRIL 124(19840-99-4)
• EPA Substance Registry System: CARBOSTYRIL 124(19840-99-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 19840-99-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Tan Solid

Uses

Suitable as a laser dye

General Description

Carbostyril 124 (CS124) is a chromophore that can be used as a laser dye for sensitization and optical detection. It acts as an antenna molecule that facilitates the light absorption and enhances fluorescence efficiency.

InChI:InChI=1/C10H10N2O/c1-6-4-10(13)12-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3,(H,12,13)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 108-45-2 m-phenylenediamine 
• 141-97-9 ethyl acetoacetate 
• 1210052-44-0 C₃₁H₄₂N₆O₁₁ 
• 156942-38-0 7-(N^α-glutaryl-L-leucyl-L-tyrosylamido)-4-methyl-2-quinolinone 
• 156942-37-9 7-(N^α-glutaryl-L-tyrosylamido)-4-methyl-2-quinolinone 
• 127556-39-2 7-(S-benzyl-L-cysteinyl-amido)-4-methyl-2-quinolinone hydrochloride 
• 137324-44-8 Z-Cys(Bzl)-Pro-NH-Meq 

Downstream Products

• 114058-74-1 2-chloro-4-methyl-7-aminoquinoline 
• 1174006-41-7 TMP-cDTPA 
• 1174006-44-0 TMP-cTTHA 

Relevant articles and documents

Antitumor agents 187: Synthesis and cytotoxicity of substituted 8,8- dimethyl-2H,8H-pyrano[6,5-h]quinoline-2-one and related compounds

Several substituted 8,8-dimethyl-2H,8H-pyrano[6,5-h]quinoline-2-ones and related compounds were synthesized and evaluated for their in vitro cytotoxicity against a panel of human tumor cell lines. The most active compound (3) showed significant cytotoxic activity with GI50 values in the micromolar range.

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Synthesis and bioactivity of 4,10-dimethyl-pyridino[2,3-h]quinolin-2(1H)-one-9-carboxylic acid and its esters

4,10-Dimethyl-pyridino[2,3-h]quinolin-2(1H)-one-9-carboxylic acid (1) was synthesized by a new approach via the key intermediate 7-[1-aza-2-(dimethylamino)vinyl]-4-methylquinolin-2(1H)-one (4). Compound 1 and its esters were evaluated in cytotoxicity and anti_HIV assays. The 9-carboxyl (1s)-endo-(-)-borneol ester (9) showed marginal cytotoxic activity in CAK1-1, HOS, KB, and HCT-8 cells.

Fluorescent retinoid X receptor ligands for fluorescence polarization assay

Retinoid X receptor (RXR) agonists are candidate agents for the treatment of metabolic syndrome and type 2 diabetes via activation of peroxisome proliferator-activated receptor (PPAR)/RXR or liver X receptor (LXR)/RXR-heterodimers, which control lipid and glucose metabolism. Reporter gene assays or binding assays with radiolabeled compounds are available for RXR ligand screening, but are unsuitable for high-throughput screening. Therefore, as a first step towards stabilizing a fluorescence polarization (FP) assay system for high-throughput RXR ligand screening, we synthesized fluorescent RXR ligands by modification of the lipophilic domain of RXR ligands with a carbostyril fluorophore, and selected the fluorescent RXR agonist 6-[ethyl(1-isobutyl-2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-7-yl)amino] nicotinic acid 8d for further characterization. Compound 8d showed FP in the presence of RXR and the FP was decreased in the presence of the RXR agonist LGD1069 (2). This compound should be a lead compound for use in high-throughput assay systems for screening RXR ligands.

Synthesis and biological evaluation of quinolone derivatives as transthyretin amyloidogenesis inhibitors and fluorescence sensors

Under certain conditions, numerous soluble proteins possess an inherent tendency to convert into insoluble amyloid aggregates, which are associated with several sporadic and genetic human diseases. Transthyretin (TTR) is one of the more than 30 human amyloidogenic proteins involved in conditions such as senile systemic amyloidosis, familial amyloid polyneuropathy, and familial amyloid cardiomyopathy. Considerable effort has been focused on identifying the native tetrameric TTR stabilizers to inhibit rate-limiting tetramer dissociation and, consequently, ameliorate TTR amyloidogenesis. Here, we describe the design and synthesis of quinolin-2(1H)-one derivatives that could be structurally complementary to the thyroxine-binding site within tetrameric TTR. Among these quinolin-2(1H)-one derivatives, compound 7a allowed 16.7% of V30M-TTR (3.6 μM) fibril formation at the same concentration and 49.6% at a concentration of 1.8 μM. Compound 7a exhibited much greater potency in complex biological samples like human plasma than that observed with tafamidis, the drug approved for the treatment of TTR amyloid cardiomyopathy for wild-type or hereditary TTR-mediated amyloidosis. Furthermore, the unique spectral properties of compound 7a demonstrated its high potential for TTR quantification, imaging sensors, and fluorescent tools to study the mechanism of TTR amyloidogenesis.

METAL CHELATORS FOR IMAGING, THERAPEUTICS, AND BIOANALYSIS

A variety of compounds are provided capable of chelating a metal, in particular a lanthanide such as Eu(III) and Tb(III). Luminescent complexes of the compound and a metal ion are also provided, in particular luminescent metal complexes are provided containing a lanthanide such as Eu(III) or Tb(III) and a compound described herein. In some aspects, the luminescent complexes are capable of exhibiting bright emissions with high quantum yields. Methods of making the compound are provided. Methods of using the compounds and luminescent complexes are also provided, for example for imaging and therapeutic applications.

Gold-Catalyzed Hydroarylation of N-Aryl Alkynamides for the Synthesis of 2-Quinolinones

A mild method for the synthesis of 2-quinolinones via hydroarylation of N-aryl alkynamides is reported. While traditional methods have relied on the use of strong Br?nsted or Lewis acids, this report describes the development of mild reaction conditions that yield 2-quinolinones in good to excellent yield using a commercially available gold catalyst. Substrates bearing a variety of functional groups are presented, with N-substitution proving to be key to the reactivity of several substrates.