Anthranils structure

NAME Methyl anthranilate STRUCTURAL FORMULA NH2 I COzCHs... 

Benzisoxazoles, also called anthranils as derivatives of anthranilic acid, are most commonly formed by the closure of bonds C(l)—C(2) or C(2)—C(3), or the introduction of atom C(3) resulting in formation of bonds C(2)—C(3) and C(3)—C(3a). As with the 1,2-benzisoxazole series, many early structural ambiguities were present in assignments (67AHC(8)277, 62HC(17)1, 66Dis(B)102). The 3-hydroxy compound is primarily in the keto form and only recently have ethers been reported. 

Figure 4.7 Two of the enzymatic activities involved in the biosynthesis of tryptophan in E. coli, phosphoribosyl anthranilate (PRA) isomerase and indoleglycerol phosphate (IGP) synthase, are performed by two separate domains in the polypeptide chain of a bifunctional enzyme. Both these domains are a/p-barrel structures, oriented such that their active sites are on opposite sides of the molecule. The two catalytic reactions are therefore independent of each other. The diagram shows the IGP-synthase domain (residues 48-254) with dark colors and the PRA-isomerase domain with light colors. The a helices are sequentially labeled a-h in both barrel domains. Residue 255 (arrow) is the first residue of the second domain. (Adapted from J.P. Priestle et al., Proc.

Priestle, J.P, et al. Three-dimensional structure of the bifunctional enzyme N-(5 -phosphoribosyl) anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escheriehia eoli. Proc. Natl. Aead. 

While this work was in progress Spath and Bretschneider showed that strychnine, on oxidation with permanganate in alkaline solution, furnished W-oxalylanthranilic acid (VII), brucine yielding oxalyl-4 5-dimethoxy-anthranilic acid, the latter observation providing confirmation of the evidence previously adduced that the two methoxy-groups in brucine are in the oj Ao-position relative to each other as indicated by Lions, Perkin and Robinson. The results so far considered indicate the presence in brucine and strychnine of the complex (VIII), which can be extended to (IX) if account is taken of the readiness with which carbazole can be obtained from strychnine and brucine and certain of their derivatives by decomposition with alkali at temperatures ranging from 200° to 400°, Knowledge of the structure of the rest of the molecule is mainly due to the results of the exhaustive study by Leuchs and his pupils of the oxidation... 

Chemical Name 2-(2,3-dimethylphenvl)amino] benzoic acid Common Name N-(2,3-xylvl)anthranilic acid Structural Formula ... 

NSAIDs are of diverse chemical structures salicylates (aspirin, sulphasalazine), indole acetic acids (indomethacin, etodolac), heteroaryl acetic acids (diclofenac), arylpropionic acids (ibuprofen, naproxen), anthranilic acids (mefenamic acid) and enolic acids (piroxicam, meloxicam). 

Another synthesis of diazepines (tricyclic) was carried out by reaction of an amino chloropyridine 258 and anthranilic acid [163]. First, a nucleophilic substitution occurred (Scheme 95) followed by an intramolecular amidation on compound 259 by microwave irradiation to give structure 260. The reaction was carried out at 100 °C for more than 2 h, a remarkably long time for a microwave-assisted reaction. 

The reagent does not replace nitrogen atoms, and N-alkyl or N-aryl anthranilic acids yield 2,l-benzisothiazoline-3-thiones (94) on heating with phosphorus pentasulfide in xylene. Curiously, when alkyl iV-arylanthranilates are treated in the same way, only a very small proportion—less than 10%— of 94 is obtained. The major product (80%) is the cyclic phosphorus-containing compound (95), the identification of which gives some clue about the structures of possible intermediates.122... 

Another multistep protocol that initially involves the formation of fused pyrimidines (quinazolines) has been described by Besson and coworkers in the context of synthesizing 8f-/-quinazolino[4,3-b]quinazolin-8-ones via double Niementowski condensation reactions (Scheme 6.250) [437]. In the first step of the sequence, an anthranilic acid was condensed with formamide (5.0 equivalents) under open-vessel microwave conditions (Niementowski condensation). Subsequent chlorination with excess POCl3, again under open-vessel conditions, produced the anticipated 4-chloro-quinazoline derivatives, which were subsequently condensed with anthranilic acids in acetic acid to produce the tetracyclic 8H-quinazolino[4,3-b]quinazolin-8-one target structures. The final condensation reactions were completed within 20 min under open-vessel reflux conditions (ca. 105 °C), but not surprisingly could also be performed within 10 min by sealed-vessel heating at 130 °C. 

In total, 185 substances were found in the wing-sac liquid of male S. bilineata from a Costa Rican population. For a more detailed analysis the relative peak area of thirteen focus compounds was compared (Table 14.1). Of these nine were male-specific substances (indole, indol-3-carboxaldehyde, indole-3-carboxylic acid, 2-aminoacetophenon, anthranilic acid, SHJOH-dipyrrolofl -aT -dJpyrazine-5,10-dione (pyrocoll), indolo[2,l-b]quinazoline-6,12-dione (tryptanthrin), 2,6,10-trimethyl-3-oxo-6,10-dodecadienolide, and a compound C15H24O2 of unknown structure), three were fatty acids (tetradecanoic acid, hexadecanoic acid, and octadecanoic acid), and one a steroid (cholesterol). On average, the cumulative peak area of these substances made up 62.5 20.7% of the whole chromatogram area. 

The low-temperature form I is stable up to 81 °C, above which temperature the structure changes to form II. Anthranilic acid I has 2 independent molecules for each asymmetric unit, one being neutral while the other has a zwitterionic form (CgThtNHs+COCP). 

Clark, L., Shah, P. S. and Mason, J. R. (1991). Chemical repellency in birds relationship between structure of anthranilate and benzoic acid derivatives and avoidance response. Journal of Experimental Zoology 269,310-322. 

Fig. 1. Structures of some bilirubin conjugates and nature of the azo derivatives obtained by treatment with diazotized ethyl anthranilate. From Fevery et al. (F5), by kind permission of the Editor of The BiochemicalJoumal.

A remarkable preference was demonstrated for one particular cocrystal, the sulfadimidineranthranilic acid (13 14) cocrystal. In a grinding competition experiment, a sulfadimidinersalicylic acid (13 15) cocrystal, for which the crystal structure had been previously determined 1391, was ground in the presence of anthranilic acid 14. The result was a displacement of salicylic acid 15 by... 

Methyl anthranilate 172 (Structure 4.51) is found in the oils of sweet orange, lemon, mandarin, bergamot, neroli and ylang-ylang oils and jasmine and tuberose absolutes. Methyl N-methyl anthranilate 173 is the main constituent of mandarin petit grain oil, and occurs also in bitter orange, mandarin and rue oils. 

Condensations of anthranilic acid derivatives lead to the 6,12-diamino- and 6,12-dioxo-dibenzodiazocines, and the dichloro compound (279) is available from the latter (54JCS3429). Reduction of (279) via the dihydrazino compound was used to prepare the parent dibenzo[6,/][l,5]diazocine (280) (67CC1077). The NMR value (5 8.53 p.p.m.) of the 6(12) proton is indicative of the diazocine structure, presumably in a tub form, rather than the valence isomeric dibenzodiazapentalene (281). 

Because benzanilides exhibit fungicidal activity 38) and anthranilic acid esters have fungicidal and bactericidal activities 39,40), Kirino et al. attempted to derive a new class of fungicides from those having a hybrid structure, methyl N-(substituted benzoyl)anthranilates 41. Among various derivatives, m-substituted compounds (19) were shown to exhibit appreciable preventive activity against powdery mildew of cucumber. 

Figure 12.6 Structures of capsaicin, maple lactone, and methyl anthranilate.

Intermolecular cyclocondensation of anthranilic acid by heating with polyphosphoric acid gave a mixture of products from which the trimer (702) having the title structure was isolated (84MI6). 

Several V02+ complexes with (107) and (108) derived from dibenzoylmethane or pyrrole-2-carboxyaldehyde and several amines (taurine, anthranilic acids, /I-alanine) were formulated as [VO(SB)(H2O)2] 780 783 it was proposed that these SBs behave as tridentate ligands and assume a monomeric structure on the basis of fiia and ebulliometric measurements in dioxane. A pyridine adduct [VO(PE)(py)2] was also obtained where PE is the SB (108 R—O = CH2CH2SOj).782... 

In the tryptophan branch (Fig. 22-17), chorismate is converted to anthranilate in a reaction in which glutamine donates the nitrogen that will become part of the indole ring. Anthranilate then condenses with PRPP. The indole ring of tryptophan is derived from the ring carbons and amino group of anthranilate plus two carbons derived from PRPP. The final reaction in the sequence is catalyzed by tryptophan synthase. This enzyme has an a2/32 subunit structure and can be dissociated into two a subunits and a /32 subunit that catalyze different parts of the overall reaction ... 

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