106435-53-4

Usage

Uses

Used in Pharmaceutical Industry:
Quinoxaline, 2-(chloromethyl)is used as a key intermediate in the synthesis of pharmaceuticals for its ability to form a wide range of biologically active molecules. Its unique structure allows for the development of new drugs with potential applications in treating various diseases and medical conditions.
Used in Material Science Industry:
In the material science industry, Quinoxaline, 2-(chloromethyl)is utilized as a precursor for the development of advanced materials with specific electronic and optical properties. Its potential use in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, is being explored due to its ability to enhance device performance and efficiency.
Used in Agrochemical Industry:
Quinoxaline, 2-(chloromethyl)is also employed as an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals. Its unique chemical properties enable the creation of innovative products that can improve crop protection and yield.
However, it is crucial to handle Quinoxaline, 2-(chloromethyl)with care, as it is an irritant to the skin, eyes, and respiratory system. Proper safety measures should be taken during its production, storage, and use to minimize potential health risks.

Upstream product

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

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 academic research and scientific papers

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.

2,6-Difluorobenzamide Inhibitors of Bacterial Cell Division Protein FtsZ: Design, Synthesis, and Structure–Activity Relationships

A wide variety of drug-resistant microorganisms are continuously emerging, restricting the therapeutic options for common bacterial infections. Antimicrobial agents that were originally potent are now no longer helpful, due to their weak or null activity toward these antibiotic-resistant bacteria. In addition, none of the recently approved antibiotics affect innovative targets, resulting in a need for novel drugs with innovative antibacterial mechanisms of action. The essential cell division protein filamentous temperature-sensitive Z (FtsZ) has emerged as a possible target, thanks to its ubiquitous expression and its homology to eukaryotic β-tubulin. In the latest years, several compounds were shown to interact with this prokaryotic protein and selectively inhibit bacterial cell division. Recently, our research group developed interesting derivatives displaying good antibacterial activities against methicillin-resistant Staphylococcus aureus, as well as vancomycin-resistant Enterococcus faecalis and Mycobacterium tuberculosis. The aim of the present study was to summarize the structure–activity relationships of differently substituted heterocycles, linked by a methylenoxy bridge to the 2,6-difluorobenzamide, and to validate FtsZ as the real target of this class of antimicrobials.

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.

A new synthesis of novel tricyclic 2(5H)-furanone heterocycles from 3,4,5-trichloro-2(5H)-furanone

A novel class of five-six-six tricyclic 2(5H)-furanone heterocycles was synthesized from 3,4,5-trichloro-2(5H)-furanone and bifunctional o-nucleophiles in a single step. In addition, 2-(chloromethyl)quinoxaline was obtained through this method, and the distinctive formation mechanism of this compound is discussed.

Substituted tetralins, chromans and related compounds in the treatment of asthma

PCT No. PCT/US87/02734 Sec. 371 Date Apr. 11, 1990 Sec. 102(e) Date Apr. 11, 1990 PCT Filed Oct. 19, 1987Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals; pharmaceutical compositions comprising said compounds; a method of treatment with said compounds; and intermediates useful in the synthesis of said compounds.

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.

Intercalator amino acids: Synthesis of heteroaryl alanines

Stereoselective alkylation of (S)-(-)-2-t-butyl-1-t-butyloxycarbonyl-3-methyl-4-imidazolinone with 2-chloromethylquinoline, 2-chloromethylquinoxaline and 5-chloromethyl-1,10-phenanthroline, followed by hydrolysis, afforded the corresponding (S)-(+)-α-amino acids with high enantiomeric excess.

Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases

Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals, pharmaceutical compositions thereof, a method of treatment therewith, and to intermediates useful in the synthesis thereof.

Side chain chlorination process of heterocycles

A novel method of chlorinating the alkyl side chains of a nitrogen containing heterocyclic comprising reacting an alkyl substituted heterocycle with trichloroisocyanuric acid at temperatures of 20° to 200° C. to obtain the same in high yields.

Side Chain Chlorinations of N-Heterocyclic Compounds by Trichloroisocyanuric Acid (TCC)

N-Heterocyclic compounds such as 2-methylpyridines, 2-methylquinoline, and 2-methylquinoxaline react with trichloroisocyanuric acid (TCC) without the addition of an initiator to provide the corresponding chloromethyl derivatives in good yields.