55687-05-3

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dichloroquinoxaline is used as a synthetic intermediate for the preparation of chloroquinoxalines from (chloro)nitroanilines. These chloroquinoxalines are key components in the development of (chloroquinoxalinyloxy)phenoxypropionic acid analogs, which exhibit antitumor properties. 2,5-Dichloroquinoxaline plays a crucial role in the synthesis of potential cancer-fighting drugs, contributing to the advancement of oncology treatments.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 1758, 2001 DOI: 10.1021/jm0005149

InChI:InChI=1/C8H4Cl2N2/c9-5-2-1-3-6-8(5)11-4-7(10)12-6/h1-4H

Upstream product

• 55687-19-9 5-chloroquinoxaline-2(1H)-one 
• 55687-19-9 5-chloro-2-quinoxalinol 
• 21745-41-5 2,3-diaminochlorobenzene 
• 347162-12-3 2-chloro-N-cyanomethyl-6-nitroaniline 
• 148010-70-2 5-chloro-3,4-dihydro-quinoxalin-2-ol 
• 769-11-9 2-chloro-6-nitroaniline 
• 347162-13-4 N-(2-chloro-6-nitrophenyl)glycine 

Downstream Products

• 97919-22-7 4-amino-N-(5-chloro-2-quinoxalinyl)benzenesulfonamide 
• 1225652-87-8 2-(3-bromophenoxy)-5-chloroquinoxaline 

Relevant academic research and scientific papers

QUINOXALINE-BASED LXR MODULATORS

Disclosed are quinoxaline-based modulators of Liver X receptors (LXRs) and related methods. The modulators include compounds of formula (I): wherein: each of L1 and L2 is, independently, a bond, —O— or —NH—;R2 is C6/

Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469)

2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469) is among the most highly and broadly active antitumor agents to have been evaluated in our laboratories and is currently scheduled to enter clinical trials in 2001. The mechanism or mechanisms of action of XK469 remain to be elaborated. Accordingly, an effort was initiated to establish a pharmacophore hypothesis to delineate the requirements of the active site, via a comprehensive program of synthesis of analogues of XK469 and evaluation of the effects of structural modification(s) on solid tumor activity. The strategy formulated chose to dissect the two-dimensional parent structure into three regions - I, ring A of quinoxaline; II, the hydroquinone connector linkage; and III, the lactic acid moiety - to determine the resultant in vitro and in vivo effects of chemical alterations in each region. Neither the A-ring unsubstituted nor the B-ring 3-chloro-regioisomer of XK469 showed antitumor activity. The modulating antitumor effect(s) of substituents of differing electronegativities, located at the several sites comprising the A-ring of region I, were next ascertained. Thus, a halogen substituent, located at the 7-position of a 2-{4-[(2-quinoxalinyl)oxy]phenoxy}propionic acid, generated the most highly and broadly active antitumor agents. A methyl, methoxy, or an azido substituent at this site generated a much less active structure, whereas 5-, 6-, 8-chloro-, 6-, 7-nitro, and 7-amino derivatives all proved to be essentially inactive. When the connector linkage (region II) of 1 was changed from that of a hydroquinone to either a resorcinol or a catechol derivative, all antitumor activity was lost. Of the carboxylic acid derivatives of XK469 (region III), i.e., CONH2, CONHCH3, CON(CH3)2, CONHOH, CONHNH2, CN, or CN4H (tetrazole), only the monomethyl- and N,N-dimethylamides proved to be active.

Antitumor compositions and methods of treatment

This invention provides certain sulfonamidoquinoxaline derivatives and methods for using them in the treatment of susceptible neoplasms in mammals. Also provided are certain novel pharmaceutical formulations employing these sulfonamidoquinoxaline derivatives, in combination with a carrier, diluent or excipient.