55687-19-9Relevant academic research and scientific papers
Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis
Huang, Lin,Xu, Jun,He, Lei,Liang, Chenfeng,Ouyang, Yani,Yu, Yongping,Li, Wanmei,Zhang, Pengfei
supporting information, p. 3627 - 3631 (2021/05/03)
Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure.
Electrochemically C-H/S-H Oxidative Cross-Coupling between Quinoxalin-2(1 H)-ones and Thiols for the Synthesis of 3-Thioquinoxalinones
Zhou, Jiadi,Li, Zhonghui,Sun, Zexu,Ren, Quanlei,Zhang, Qiwei,Li, Hu,Li, Jianjun
, p. 4365 - 4372 (2020/04/10)
An electrochemical method for the C(sp2)-H thioetherification of quinoxalin-2(1H)-ones with primary, secondary, and tertiary thiols has been reported. Various quinoxalin-2(1H)-ones underwent this thioetherification smoothly under metal- A nd chemical oxidant-free conditions, affording 3-alkylthiol-substituted quinoxalin-2(1H)-ones in moderate to good yields.
QUINOXALINE-BASED LXR MODULATORS
-
Page/Page column 29, (2010/06/11)
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)
Hazeldine,Polin,Kushner,Paluch,White,Edelstein,Palomino,Corbett,Horwitz
, p. 1758 - 1776 (2007/10/03)
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.
High-affinity partial agonist imidazo[1,5-a]quinoxaline amides, carbamates, and ureas at the γ-aminobutyric acid A/benzodiazepine receptor complex
Jacobsen, E. Jon,TenBrink, Ruth E.,Stelzer, Lindsay S.,Belonga, Kenneth L.,Carter, Donald B.,Im, Haesook K.,Im, Wha Bin,Sethy, Vimala H.,Tang, Andy H.,VonVoigtlander, Philip F.,Petke, James D.
, p. 158 - 175 (2007/10/03)
A series of imidazo[1,5-a]quinoxaline amides, carbamates, and ureas which have high affinity for the γ-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies ranging from antagonists to full
