87378-87-8Relevant academic research and scientific papers
Bioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols
Fu, Hua,Li, Hongyun,Li, Youshan,Lou, Zhenbang,Yang, Haijun,Zhao, Yufen
supporting information, p. 3671 - 3677 (2020/02/04)
A bioorthogonal ligation and cleavage method via reactions of chloroquinoxalines (CQ) and ortho-dithiophenols (DT) is presented. Double nucleophilic substitutions of ortho-dithiophenols to chloroquinoxalines provide conjugates containing tetracyclic benzo[5,6][1,4]dithiino[2,3-b]quinoxaline with strong built-in fluorescence together with release of the other functional molecules. Three cleavable linkers were designed and successfully used in release of the molecules containing biotin from the protein conjugates. The CQ-DT bioorthogonal reactions can be applied for the bioorthogonal ligations, bioorthogonal cleavages, and trans-tagging of proteins, and show advantages of readily accessible unnatural orthogonal groups, appealing reaction kinetics (k2≈1.3 m?1 s?1), excellent biocompatibility of orthogonal groups, and high stability of conjugates. This complements previous bioorthogonal reactions and is a new route for protein-fishing applications and in-gel fluorescence analysis.
NUCLEOPHILIC SUBSTITUTIONS ON 2-CHLORO-3-NITROQUINOXALINE
Nasielski-Hinkens, R.,Kaisin, M.,Grandjean, D.,Loos, M.,Nasielski, J.
, p. 919 - 926 (2007/10/02)
Piperidine, cyclohexylamine, methoxide ion and para-thiocresolate ion react with 2-chloro-3-nitroquinoxaline 1 by selectively substituting the nitro group, in contrast to be behavior of most ortho-chloronitroaromatics which loose halide when subjected to nucleophilic substitution reactions.This inversion is interpreted as being due to the lack of activation of the 2-position by the nitro group in the 3-position because of the low value of the ?-bond index between these two vertices.It is also suggested that the substitution by neutral reagents such as amines is strongly influenced by stabilizing interactions between the negatively charged nitro group and the ammonium moiety in the ? complex; this built-in solvation may be responsible for inversions in the chemoselectivity between chloro and nitro nucleofugicities.
Some Sulfur-containing Quinoxalines (1)
Campaigne, E.,McLaughlin, Astley R.
, p. 623 - 628 (2007/10/02)
A series of quinoxalines having oxygen, chlorine or sulfur substituted at the 2-position and long-chain alkyl, alkylthio, arylthio, alkylthioalkyl or arylthioalkyl groups at the 3-position have been synthesized.
