1501-41-3

Basic information

• Product Name: 3-(bromomethyl)-1-methylquinoxalin-2(1H)-one
• CAS NO: 1501-41-3
• Molecular Formula: C₁₀H₉BrN₂O
• Molecular Weight: 253.0953
• Mol File: 1501-41-3.mol

Chemical Properties

• Boiling Point: 350.4°C at 760 mmHg
• Flash Point: 165.7°C
• Density: 1.57g/cm³
• Vapor Pressure: 4.42E-05mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 3-(bromomethyl)-1-methylquinoxalin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(bromomethyl)-1-methylquinoxalin-2(1H)-one(1501-41-3)
• EPA Substance Registry System: 3-(bromomethyl)-1-methylquinoxalin-2(1H)-one(1501-41-3)

Safety Data

• Hazardous Substances Data: 1501-41-3(Hazardous Substances Data)

Upstream product

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 3149-25-5 1,3-dimethyl-1H-quinoxalin-2-one 
• 127-09-3 sodium acetate 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 95-54-5 1,2-diamino-benzene 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 

Downstream Products

• 791068-34-3 3-(benzylamino-methyl)-1-methyl-1H-quinoxalin-2-one 
• 791068-36-5 (S)-1-methyl-3-[(1-phenyl-ethylamino)methyl]-1H-quinoxalin-2-one 
• 791068-35-4 (R)-1-methyl-3-[(1-phenyl-ethylamino)methyl]-1H-quinoxalin-2-one 

Relevant articles and documents

C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.

QUINOXALINONE-3- ONE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

The invention relates to quinoxalinone derivatives of general Formula (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.General Formula (I) wherein X and R1-R9 are as defined in the description

Novel compounds for enhancing chemotherapy

The present invention provides chemical compounds, pharmaceutical compositions, and methods for increasing the therapeutic efficacy of drugs. Specifically, the invention provides compounds and compositions for inhibiting drug transport proteins that efflu

Structure-activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists

A significant problem in the clinical treatment of cancer relates to the development of tumor resistance to many chemotherapeutic agents. Acquired drug resistance is often mediated through overexpression of membrane transport proteins that effectively efflux anticancer agents. Two of the best-studied transporters, P-glycoprotein (Pgp) and MRP1, have pharmacological properties that only partially overlap. In our search for improved drug-resistance antagonists, we have identified a family of substituted quinoxalines that selectively antagonizes Pgp over MRP1. Consequently, a focused library of congeners was designed and synthesized starting with a parent bromomethylquinoxalinone. This parent quinoxalinone was then condensed with a series of phenols to yield a family of substituted phenoxymethylquinoxalinones. These compounds were evaluated for their toxicity toward drug-sensitive MCF-7 breast carcinoma cells and for their abilities to antagonize Pgp and MRP1 in drug-resistant cell lines (NCI/ADR and MCF-7/VP, respectively). The results of this structure-activity study indicate that compounds with carbonyl substitutions of the phenoxy group (ester, amide, or ketone moieties) demonstrate excellent antagonism of Pgp while having relatively low toxicity toward drug-sensitive cells. Importantly, none of these compounds antagonized MRP1. Because of their transporter selectivity, we predict that substituted quinoxalinones may be more effective MDR modulators in vivo than are nonselective transporter antagonists.

Quinoxalinone compounds useful for expanding the lumina or air passages in mammals

Compounds of the formula below are useful for expanding the lumina or air passages in a mammal in need of said treatment. The compounds are also useful for treating atopic eczema and urticaria. STR1 wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, alkyl of one to four carbon atoms, inclusive, alkoxy of one to four carbon atoms, inclusive, and cyano; R1 is hydrogen, methyl or ethyl; R2 is hydrogen, alkyl of one to six carbon atoms, inclusive, phenyl, benzyl, CH2 Z wherein Z is fluoro, chloro, or bromo, CO2 M, CH2 CO2 M, CH2 CH2 CO2 M and CHR3 CO2 M wherein M is hydrogen, alkyl of one to four carbon atoms, inclusive, or a physiologically acceptable metal or amine cation and R3 is alkyl of one to three carbon atoms, inclusive, with the proviso that M is not hydrogen when R2 is CH2 CO2 M or a CHR3 CO2 M.