Amido benzoic acids

Methyl Anthranilate.—This ester is one of extreme importance, and to it is largely due the possibility of manufacturing artificial neroli oils. It was discovered as a constituent of neroli oil in 1895 by Walbaum, and has since been identified in numerous other flower oils, such as tuberose, ylang-ylang, jasmin, and gardenia. Its value in synthetic perfumery is therefore obvious. Its constitution is that of a methyl ester or orthp-amido-benzoic acid, of the formula here shown —... 

Further, the reaction is of practical value in the preparation of o-amido-benzoic acid, used in the manufacture of artificial indigo. If, as above, bromine and caustic potash are allowed to act on phthalimide, there is first formed, by the addition of water, an add-amide ... 

A simple example in this class with which to begin is A,A-diethyl-m-to-luamide 0V,/V-dicthyl-3-mcthylbenzamidc, DEET, 4.82), an extensively used topical insect repellant. The hydrolysis product 3-methylbenzoic acid was detected in the urine of rats dosed intraperitoneally or topically with DEET. However, amide hydrolysis represented only a minor pathway, the major metabolites resulting from methyl oxidation and A-dealkylation [52], Treatment of rats with /V,/V-dicthylbcnzamidc (4.83), a contaminant in DEET, produced the same urinary metabolites as its secondary analogue, A-ethylbenzamide (see Sect. 4.3.1.2). This observation can be explained by invoking a metabolic pathway that involves initial oxidative mono-A-deethylation followed by enzymatic hydrolysis of the secondary amide to form ethylamine and benzoic acid [47], Since diethylamide was not detected in these experiments, it appears that A,A-diethylbenzamide cannot be hydrolyzed by amidases, perhaps due to the increased steric bulk of the tertiary amido group. 

The next example is 1,3-dibenzoylurea (4.222), a diacetylated linear urea. The hydrolysis kinetics and enzymatic cleavage of 1,3-dibenzoylurea together with various other /V-acylbenzamides were studied to assess the suitability of these compounds as prodrugs for the amido group [113]. At pH 7.4 and 37°, 1,3-dibenzoylurea was hydrolyzed quantitatively to benzoic acid and N-benzoylurea (4.223) with a tm value of 39 h. Since the hydrolysis of 1,3-di-benzoylurea was not catalyzed by human plasma, it was concluded that the acyclic diureide structure is not appropriate in prodrug design. 

Plant. In plants, the cyano group is hydrolyzed to an amido group which is subsequently oxidized to a carboxylic acid. Hydrolyzes to hydroxybenzoic acid (Hartley and Kidd, 1987). In plants, bromoxynil may hydrolyze to a benzoic acid (Humburg et al., 1989). Bromoxynil-resistant cotton was recently developed by inserting a bxn gene cloned from the soil bacterium Klebsiella ozaenae. This gene, which encodes a specific nitrolase, converted bromoxynil to its primary metabolite 3,5-dibromo-4-hydroxybenzoic acid (Stalker et al, 1988). 

Recently fluorinated chains were also attached to amine based dendrimers, like PPI and poly(amido amine) (PAMAM), by means of ionic self assembly with semiperfluorinated alkanoic acids (Fig. 71, 216, 217). All dendrimer complexes 216 with perfluorinated alkanoic acids show SmA phases except the fifth generation dendrimer which shows a Colrec phase [378]. Also semiperfluorinated 4-alkoxybenzoic acids 217 [379] and mixed systems combining fluorinated and nonfluorinated alkanoic or benzoic acids (216, 217) have been reported [379-381]. In most cases layer structures (SmA) and for higher generation dendrimers also modulated SmA phases (Colrec phases) were observed. The layer thickness of the SmA phases of the mixed complexes 216 depends on the ratio of fluorinated and non-fluorinated acids, where smaller d values were observed for dendrimers with low Rp-content for Rp-rich dendrimers the more rigid Rp-chains provide... 

The reaction of benzoic acid hydrazide with carbon disulfide in basic medium was first described by Busch and Starke (63) who identified the reaction product as benzoyldithiocarbazic acid (LXXXII). Hog-garth (767) found, that, in the absence of alkali, 5-phenyl-Z]4-l,3.4-oxadiazoline-2-thione (LXXXIII) and 1,2-dibenzoylhydrazine were formed in the reaction of benzoic acid hydrazide with carbon disulfide. If this same reaction is carried out in pyridine, there is formed, beside 5 -phenyl-J 4-1,3,4-oxadiazoline-2-thione (LXXXI11), 3 -phenyl-4-ben z-amido-J2"I>2,4-triazoline-5-thione (LXXXV), probably from the intermediately formed t,5-dibenzoylthiocarbohdrazide (LXXXIV). 

Metrizoic Acid. 3-(Acetylamino)-5-(acetylmethyl-amino)-2,4,6-triiodobenzoic acid 3-acetamido-2,4,6-triiodo-5-(N-methylacetamido) benzoic acid N-methyl-3,5 -diacet-amido-2,4,6 triiodobenzoic acid. mol wt... 

Amidotrizoate meglumine Angiografin Angiovist 282 Benzoic acid, 3,5-diacetamido-2,4,6-triiodo-, compd. with 1-deoxy-1-(methylamino)-D-glucitol 3,5-Bis(acet-amido)-2,4,6-... 

Solubility op the Three Isomeric Amido Nitro Benzoic Acids. 

Hippuric acid—Benzyl-glycocol—Benzyl-amido-acetic acid— CHa,[NH(C H6CO)],COOH—179—is a constant constituent of the urine of the herbivora, and of human urine to the extent of 0.29-2.84 grams (4.5-43.8 grains) in 34 hours. It is more abundant with a purely vegetable diet, after the administration of benzoic acid, and in diabetes mellitus and chorea. 

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