106435-53-4

Basic information

• Product Name: Quinoxaline, 2-(chloromethyl)-
• Synonyms: Quinoxaline, 2-(chloromethyl)-
• CAS NO: 106435-53-4
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.62
• Mol File: 106435-53-4.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Quinoxaline, 2-(chloromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoxaline, 2-(chloromethyl)-(106435-53-4)
• EPA Substance Registry System: Quinoxaline, 2-(chloromethyl)-(106435-53-4)

Safety Data

• Hazardous Substances Data: 106435-53-4(Hazardous Substances Data)

Usage

General Description

Quinoxaline, 2-(chloromethyl)- is a chemical compound with the molecular formula C9H7ClN2. It is a chloromethyl derivative of quinoxaline, which is a heterocyclic compound containing a benzene ring fused to a pyrazine ring. Quinoxaline, 2-(chloromethyl)- has potential applications in the pharmaceutical and material science industries. It is commonly used as an intermediate in the synthesis of other organic compounds, including pharmaceuticals and agrochemicals. Additionally, it has been studied for potential use in organic electronic devices due to its electronic and optical properties. However, it is important to handle this compound with caution as it is an irritant to the skin, eyes, and respiratory system.

Upstream product

• 7251-61-8 2-methylquinoxaline 
• 87-90-1 trichloroisocyanuric acid 
• 95-54-5 1,2-diamino-benzene 
• 19714-00-2 2,3,4-trichlorodihydrofuran-1-one 
• 497-19-8 sodium carbonate 
• 112193-05-2 2-<(E)-2-Phenylethenyl>chinoxalin 
• 41242-94-8 2-hydroxymethylquinoxaline 

Downstream Products

• 950698-97-2 3-{3-tert-butylsulfanyl-1-[4-(6-methoxypyridin-3-yl)benzyl]-5-(quinoxalin-2-ylmethoxy)-1H-indol-2-yl}-2,2-dimethylpropionic acid 
• 1346434-78-3 3-[3-tert-butylsulfanyl-1-[4-(6-methoxypyridin-3-yl)benzyl]-5-(quinoxalin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionicacid ethyl ester 
• 1027304-01-3 2-{cyclohexyl-[4-(quinoxalin-2-ylmethoxy)-phenyl]-methoxy}-isoindole-1,3-dione 
• 1026345-32-3 O-{cyclohexyl-[4-(quinoxalin-2-ylmethoxy)-phenyl]-methyl}-hydroxylamine 
• 263257-21-2 cyclohexyl(4-(2-quinoxalylmethoxy)phenyl)methanol 

Relevant articles and documents

Microwave-assisted α-halogenation of 2-methylquinolines with tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane)

A simple and efficient methodology permitting the halogenation of 2-methylquinolines into 2-(chloromethyl)quinolines or 2-(bromomethyl)quinolines in the tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane) system has been developed for the first time. The halogenation can be rapidly completed with good to excellent yields and high selectivity under microwave irradiation.

5-lipoxygenase-activating protein (FLAP) inhibitors. Part 4: Development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin- 2-ylmethoxy)-1 H -indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor

The potent 5-lipoxygenase-activating protein (FLAP) inhibitor 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2- ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid 11cc is described (AM803, now GSK2190915). Building upon AM103 (1) (Hutchinson et al. J. Med Chem.2009, 52, 5803-5815; Stock et al. Bioorg. Med. Chem. Lett. 2010, 20, 213-217; Stock et al. Bioorg. Med. Chem. Lett.2010, 20, 4598-4601), SAR studies centering around the pyridine moiety led to the discovery of compounds that exhibit significantly increased potency in a human whole blood assay measuring LTB4 inhibition with longer drug preincubation times (15 min vs 5 h). Further studies identified 11cc with a potency of 2.9 nM in FLAP binding, an IC50 of 76 nM for inhibition of LTB4 in human blood (5 h incubation) and excellent preclinical toxicology and pharmacokinetics in rat and dog. 11cc also demonstrated an extended pharmacodynamic effect in a rodent bronchoalveolar lavage (BAL) model. This compound has successfully completed phase 1 clinical studies in healthy volunteers and is currently undergoing phase 2 trials in asthmatic patients.

Heteroarylmethoxyphenylalkoxyiminoalkylcarboxylic acids as leukotriene biosynthesis inhibitors

A novel series of heteroarylmethoxyphenylalkoxyiminoalkylcarboxylic acids was studied as leukotriene biosynthesis inhibitors. A hypothesis of structure-activity optimization by insertion of an oxime moiety was investigated using REV-5901 as a starting point. A systematic structure- activity optimization showed that the spatial arrangement and stereochemistry of the oxime insertion unit proved to be important for inhibitory activity. The promising lead, S-(E)-11, inhibited LTB4 biosynthesis in the intact human neutrophil with IC50 of 8 nM and had superior oral activity in vivo, in a rat pleurisy model (ED50 = 0.14 mg/kg) and rat anaphylaxis model (ED50 = 0.13 mg/kg). In a model of lung inflammation, S-(E)-11 blocked LTE4 biosynthesis (ED50 of 0.1 mg/kg) and eosinophil influx (ED50 of 0.2 mg/kg). S-(E)-11 (A-93178) was selected for further preclinical evaluation.