2226-83-7Relevant academic research and scientific papers
The conversion of a phenol to an aniline occurs in the biochemical formation of the 1-(4-aminophenyl)-1-deoxy- d -ribitol moiety in methanopterin
White, Robert H.
experimental part, p. 6041 - 6052 (2012/06/04)
Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-d-ribitol (APDR) moiety present in the C1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(β-d-ribofuranosyl)hydroxybenzene 5′-phosphate (β-RAH-P). The β-RAH-P then condenses with l-aspartate in the presence of ATP to form 4-(β-d-ribofuranosyl)-N-succinylaminobenzene 5′-phosphate (β-RFSA-P). Elimination of fumarate from β-RFSA-P produces 4-(β-d-ribofuranosyl)aminobenzene 5′-phosphate (β-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.
2-Carboxytetrahydroquinolines. Conformational and Stereochemical Requirements for Antagonism of the Glycine Site on the NMDA Receptor
Carling, Robert W.,Leeson, Paul D.,Moseley, Angela M.,Baker, Raymond,Foster, Alan C.,et al.
, p. 1942 - 1953 (2007/10/02)
2-Carboxy-1,2,3,4-tetrahydroquinoline derivatives, derived from kynurenic acid, have been synthesized and evaluated for in vitro antagonist activity at the glycine site on the NMDA receptor. 2,3-Dihydrokynurenic acids show reduced potency relative to the
1-ARYL-5-CARBOXYMETHYLHYDANTOIN DERIVATIVES. STRUCTURE OF 1-PHENYL-2-THIO-5-CARBOMETHOXYMETHYLHYDANTOIN
Baltrushis, R. S.,Beresnevichyus, Z.-I. G.,Vizgaitis, I. M.,Gatilov, Yu. V.
, p. 1226 - 1231 (2007/10/02)
The reaction of aromatic amines with maleic acid or its diethyl ester with subsequent hydrolysis gave N-arylaspartic acids, which were converted to 1-aryl- and 1-aryl-2-thio-5-carboxymethylhydantoins by the action of urea, cyanates, or thiocyanates in an
