6641-44-7Relevant articles and documents
1,2,3-Triazoles based 3-substituted 2-thioquinoxalines: Synthesis, anti-bacterial activities, and molecular docking studies
Keivanloo, Ali,Fakharian, Mahsa,Sepehri, Saghi
, (2020)
New 1,2,3-triazoles based on 3-Substituted 2-thioquinoxalines were synthesized via a copper-catalyzed click reaction. The new 1,2,3-triazoles were screened for their in vitro antibacterial activities and were subjected to molecular docking studies. The starting materials included, 3-substituted-2-propargylthioquinoxalines were prepared from 2,3-dichloroquinoxaline, aliphatic amines, sodium sulfide, and propargyl bromide. The click of 2-propargythioquinoxalines with aryl azides catalyzed by copper(II) salen complex afforded novel 1,2,3-triazole-linked thioquinoxalines derivatives. The use of salen copper(II) complex as a catalyst, increased the reaction rate and reduced the loading of the toxic copper species. Results obtained from the in vitro anti-bacterial activities of the synthesized compounds revealed that compounds 7e, 7g, and 7k are active against Bacillus subtilis and Micrococcus luteus bacteria. Furthermore, in silico molecular docking results stipulated a sign of good correlation between experimental activity and calculated binding affinity. Docking studies proved 7e as the most potent compound. In addition, the binding maps exhibited activities that may attribute to the existence of electron donating and lipophilic group at para position of phenyl ring and hydrophobic interactions and hydrogen bond with the protein active sites.
Novel multi-component synthesis of 1,4-disubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed coupling reaction/hetero-annulation in water
Keivanloo, Ali,Kazemi, Shaghayegh Sadat,Nasr-Isfahani, Hossein,Bamoniri, Abdolhamid
supporting information, p. 6536 - 6542 (2016/09/23)
1,4-Disubstituted pyrrolo[1,2-a]quinoxalines were prepared through the one-pot multi-component reactions of 3-substituted-2-chloroquinoxalines, propargyl alcohol, and secondary amines, catalyzed by Pd/Cu, in the presence of K2CO3and sodium dodecyl sulfate (SDS) in water. This process provided a facile, eco-friendly, and highly efficient method for the synthesis of new pyrrolo[1,2-a]quinoxalines in water with good yields.
Efficient diverse approach for quinoxaline-derived glycosylated and morphinylated analogs
Beldi, Razika,Atta, Kamal F.,Aboul-Ela, Sallah,El Ashry, El Sayed H.
, p. 50 - 56 (2011/04/16)
Sulfanyl-glycosides have been synthesized by reaction of 2,3-dimercaptoquinoxaline (1) with acetohalo sugars in presence of base to give the thioglycosides-derived quinoxalines 5-7 and 9. Similarly, the acyclic analogs 23-26 were prepared by coupling of 1 with different acyclo-alkylating agents. The preparation of 3-morpholinyl-quinoxalines 10 and 11 allowed the synthesis of 3-glycosylsulfanyl-2-morpholinyl-quinoxalines 12-14 and 17 as well as the acyclic analogs 27-29. Microwave irradiation of the reactants turned out to be preferred over the conventional method for achieving the synthetic goals. This study made an available venue to the synthesis of diverse quinoxaline derivatives.
