Nilic acid

Acridone (I) can be readily prepared by the cyclisation of. V-pheiiylantlira-nilic acid (p. 217) using sulphuric acid. Many substituted acridones may be... 

A more elaborate example is the Niementowski reaction to give access to quinazo-linones and quinolines [62], The determining step consists in the reaction of anthra-nilic acid with some amides or ketones (Eq. 11). 

Cuscutic resinoside A (1 tetradecanoic acid, (115)-[[6-deoxy-3-(9-(6-deoxy-a-L-mannopyranosyl)-4-0-[(2/ ,3R)-3-hydroxy-2-niethyl-l-oxobutyl]-a-L-nianno-pyranosyl]oxy]-intramol. l,2 -ester) was obtained from the ethyl acetate-soluble fraction of a methanol extract prepared from the seeds of Cuscuta chinensis Lam. The purification of this compound employed a combination of column and preparative-scale HPLC. The structure was deduced from spectroscopic evidence and acid hydrolysis 14). The degradative process gave convolvuUnolic acid, nilic acid, and L-rhamnose. The sugar components were identified by GC analysis after being converted to their thiazolidine derivatives. This disaccharide has a unique macrocyclic lactone, which is placed between C-1 and C-2 of the first rhamnose moiety. 

Antimicrobial sulpha drugs, e.g. sulphanilamide, are the amide of sulpha-nilic acid, and certain related substituted amides. Sulphanilamide, the first of the sulpha drugs, acts by inhibiting the bacterial enzyme that incorporates para-aminobenzoic acid into folic acid. Sulphanilamide is a bacteriostatic drug, i.e. inhibits the further growth of the bacteria. 

J. C. Bigge, T. P. Patel, J. A. Bruce, P. N. Goulding, S. M. Charles, and R. B. Parekh, Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthra-nilic acid, Anal. Biochem., 230 (1995) 229-238. 

Caproic acid, as glycogenic agent, II, 134 labelled with isotopic C, III, 231 —, deuterio-, metabolism of, II, 152 Caprylic acid, as glycogenic agent, II, 134 labelled with isotopic C, III, 231 metabolism of, II, 152 Carbamic acid, N-phenyl. See Carba-nilic acid. 

In the present report, the use of radioiodinated diazotized iodosulfa-nilic acid and a lactoperoxidase-catalyzed iodination method for the labeling and examination of plasma membrane proteins and lipids in cells under humoral immune attack is described. 

In the same year paper chromatography was first attempted by Benassi (B4) for the simultaneous analysis of 8 tryptophan metabolites (kyn-urenine, 3-hydroxykynurenine, kynurenic acid, xanthurenic acid, anthra-nilic acid, 3-hydroxyanthranilic acid, 2-aminoacetophenone, and 2-amino-3-hydroxyacetophenone), separated by means of a mixtiue of methanol, n-butanol, benzene, and water and revealed through the fluorescence in ultraviolet light of 3655 A. Each compound elicits a different fluorescent color (cf. Table 1). 

Among the active compounds were xanthurenic and 3-hydroxyanthra-nilic acids, whereas tryptophan, kynurenine, and kynurenic, anthranilic, and nicotinic acids were unable to cause deiodination. These findings support, according to the authors, the view that the deiodination of the thyroid hormone may be closely associated with its biological action. 

Also Tojo and Uenoyama (T2) by means of paper chromatography detected neither 5-hydroxyanthranilic acid nor its conjugate forms in urine of senile cataract patients. They found, however, an ethanol-extractable substance giving a positive ninhydrin reaction and Rf value coinciding with that of tryptophan. The oral administration of a dose of anthra-nilic acid did not alter their findings. 

The disease is a rare inherited disorder characterized by a progressive degeneration of the lenticular nucleus in the brain and by cirrhosis of the liver. Barbeau et al. (Bl) studied a case of Wilson s disease which presented normal ceruloplasmin and serum copper values but increased excretion of kynurenine, 3-hydroxykynurenine, and conjugated anthra-nilic acid in xurine after an oral dose of 2 g L-tryptophan. This defect in tryptophan metabolism could be related to that of other amino acids and to the actual content of ceruloplasmin in Wilson s disease (Bl). These findings corroborated Marver s (M2) investigations demonstrating a definite excretion of kynurenine and 3-hydroxykynurenine in abnormal proportions after a tryptophan load in a case of Wilson s disease. 

According to Zini (Zl), prolonged oral treatment with isonicotinic acid hydrazide interfered with tryptophan metabolism, probably by inhibiting kynureninase activity, which catalyzes the synthesis of anthra-nilic acid from kynurenine. 

The main adverse effects of tolfenamic acid (particularly nephrotoxicity) are similar to those of the other anthra-nilic acid derivatives. However, dysuria has been reported more often and confirmed by rechallenge (SEDA-4, 68). 

A. o-Hydrazinobenzoic acid hydrochloride. In a 2-1. beaker, provided with a stirrer and a low-temperature thermometer, and cooled in an ice-salt bath, are placed 42 g. (0.31 mole) of anthra-nilic acid and 300 ml. of water. The stirrer is started, and 340 ml. of concentrated hydrochloric acid (sp. gr. 1.18) is added in one portion the anthranilic acid dissolves, and its hydrochloride begins to separate almost immediately. After the mixture has been cooled to 0°, a solution of 21.6 g. (0.31 mole) of technical sodium nitrite in 210 ml. of water is added from a dropping funnel, the tip of which extends below the surface of the suspension, at such a rate that the temperature never rises above 3°. The addition requires about 30 minutes stirring is continued for 15 minutes longer, and at the end of this period a positive test with starch-iodide paper should be obtained (Note 1). The dear brown solution is then diluted with 150 ml. of ice water. 

Studies by Thomas and Stocker180 and Christen et al.181 indicated that the formation and release of the aminophenolic antioxidant 3-hydroxyanthra-nilic acid (3-HAA) via the kynurenine pathway are responsible for the ability of interferon-y-primed human macrophages to inhibit the oxidation of low-density lipoprotein (LDL), an event implicated as an important event in atherogenesis. 3-HAA efficiently inhibits LDL oxidation by acting as an aqueous oxidant scavenger and a synergist for LDL-associated vitamin E. 

Jahnke, M., T. El-Banna, R. Klintworth, and G. Auling. 1990. Mineralization of ortha-nilic acid is a plasmid-associated trait in Alcaligenes sp. 0-1. /. Gen. Microbiol. 136 2241-2249. 

N,N-Diallylanthranilic acid (IX) was prepared from anthra-nilic acid (24.6 g, 0.2 mol) and allylbromide (25 g, 0.20 mol) dissolved in 40 mL of ethanol and refluxed for 8 hr. The solution was basified by an equivalent amount of aqueous... 

Agents that are oxidatively activated and inactivate the enzyme by covalently binding to it include (a) diverse sulfur compounds (e.g., carbon disulfide , parathion -, diethyldithiocarbamate , isothiocyanates , thioureas , thiophenes , tie-nilic acid - - , and mercaptosteroids , (b) halo-genated structures such as chloramphenicoF- , A-monosubstituted dichloroacetamides , and N-(2-p-nitrophenethyl)dichloroacetamide , (c) alkyl and aryl olefins and acetylenes such as... 

Koenigs, L.L., R.M. Peter, A.P. Hunter, R.L. Haining, A.E. Rettie, T. Friedberg et al. (1999). Electrospray ionization mass spectrometric analysis of intact cytochrome P450 Identification of tie-nilic acid adducts to P450 2C9. Biochemistry 38, 2312-2319. 

Lopez-Garcia, M.P., P.M. Dansette, and D. Mansuy (1993). Thiophene derivatives as new mechanism-based inhibitors of cytochromes P450 Inactivation of yeast-expressed human liver P450 2C9 by tie-nilic acid. Biochemistry 33, 166-175. 

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