1753-20-4Relevant academic research and scientific papers
An improved procedure for the nitration of benzo-2,1,3-selenadiazoles and their reduction to ortho-phenylenediamines
Wright,McClure
, p. 1023 - 1026 (2004)
A method for the nitration of benzo-2,1,3-selenadiazoles using nitric acid dissolved in a mixture of methanesulfonic acid and phosphorus pentoxide at room temperature is presented. The SN2Ar displacement of fluoride that is observed when sulfur
Synthesis and structure-activity relationships of substituted 1,4- dihydroquinoxaline-2,3-diones: Antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors
Keana,Kher,Sui Xiong Cai,Dinsmore,Glenn,Guastella,Huang,Ilyin,Lu,Mouser,Woodward,Weber
, p. 4367 - 4379 (2007/10/02)
A series of mono-, di-, tri-, and tetrasubstituted 1,4- dihydroquinoxaline-2,3-diones (QXs) were synthesized and evaluated as antagonists at N-methyl-D-aspartate (NMDA)/glycine sites and α-amino-3- hydroxy-5-methylisoxazole-4-propionic acid-preferring non-NMDA receptors. Antagonist potencies were measured by electrical assays in Xenopus oocytes expressing rat whole brain poly(A)+ RNA. Trisubstituted QXs 17a (ACEA 1021), 17b (ACEA 1031), 24a, and 27, containing a nitro group in the 5 position and halogen in the 6 and 7 positions, displayed high potency (K(b) ~ 6-8 nM) at the glycine site, moderate potency at non-NMDA receptors (K(b) = 0.9-1.5 μM), and the highest (120-250-fold) selectivity in favor of glycine site antagonism over non-NMDA receptors. Tetrasubstituted QXs 17d,e were more than 100-fold weaker glycine site antagonists than the corresponding trisubstituted QXs with F being better tolerated than Cl as a substituent at the 8 position. Di- and monosubstituted QXs showed progressively weaker antagonism compared to trisubstituted analogues. For example, removal of the 5-nitro group of 17a results in a ~100-fold decrease in potency (10a,b,z), while removal of both halogens from 17a results in a ~3000-fold decrease in potency (10v). In terms of steady-state inhibition, most QX substitution patterns favor antagonism at NMDA/glycine sites over antagonism at non-NMDA receptors. Among the QXs tested, only 17i was slightly selective for non- NMDA receptors.
Nitration of 5-Fluoro-2,1,3-benzoselenadiazoles, and the Synthesis of 4-Fluoro-3-nitro-, 4-Fluoro-6-nitro, 5-Fluoro-3-nitro-o-phenylenediamines and 3,4-Diamino-2-nitrophenols by Subsequent Deselenation
Tian, Wei,Grivas, Spiros,Olsson, Kjell
, p. 257 - 262 (2007/10/02)
Fuming nitric and concentrated sulfuric acids converted the title benzoselenadiazoles 1 and 8 into their 4- and/or 7-nitro derivatives.Unlike the m-fluoronitro substituted products 6 and 9, the o-fluoronitro substituted products 2 were accompanied by the
