Naphthalene carboxylate

These arotinoids, which were first introduced for the treatment of skin diseases, may also have potential as anticancer diugs. For example, the synthetic retinoid 6-[3-(l-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) has been shown to induce apoptosis in a variety of cancer cells including lung cancer cells in vitro, and studies concerning the use of this agent in vivo would be desirable. 

Naphthalene carboxylate dioxygenase Pseudomonas putida U103 1976 [237] [224]... 

In contrast to 2,3-dioxygenases, the related ipso/ortho oxygenation of aryl carbox-ylates has received considerable less attention and has hardly been utilized by the synthetic community, so far. Biooxidation of benzoic acid and P-naphthalene carboxylate provide access to corresponding 1,2-dihydroxylated dihydroaryl compounds in excellent stereoselectivity (Scheme 9.35), analogous to TDO- and NDO-mediated ortho/meta oxygenations. Whole-cell-mediated biotransformations were performed with mutant strains of Rahtonia and Pseudomonas and enable access to preparative quantities in >5 gl titers [261,262]. 

Less attention has been devoted to the degradation of naphthols and naphthalene carboxylates ... 

Althongh the degradation of naphthalene-2-carboxylate by Burkholderia sp. strain JT 1500 involves the formation of 1-hydroxy naphthalene-2-carboxylate, this is not formed from the expected (l/ ,25)-di-l,2-dihydrodiol-2-naphthoate. Possibly, therefore, the reaction is carried out by a monooxygenase, or a dehydration step is involved. Subsequent reactions produced pyruvate and o-phthalate that was degraded via 4,5-dihydroxyphthalate (Morawski et al. 1997). Degradation of naphthalene carboxylates formed by oxidation of methyl groups has already been noted. 

Recently, a large anionic pigment has been intercalated into an LDH host by ion-exchange of an Mg/Al LDH nitrate precursor with a solution of C.I. Pigment Red 48 2 (the calcium salt of 4-((5-chloro-4-methyl-2-sulfophenyl)azo)-3-hydroxy-2-naphthalene-carboxylic acid), in ethane-1,2-diol [215]. The UV-visible diffuse reflectance spectra of C.I. Pigment Red... 

Methoxy-7-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene 2-Naphthalene-carboxylic acid, 5,6,7,8-tetrahydro-3-methoxy-, methyl ester (78112-34-2), 65, 98 Methyl acrylate (96-33-3), 66, 54, 59 dimerization by Pd(II), 66, 52 Methylamine, N-benzylidene-, 65, 140 METHYL 4-0-BENZOYL-6-BROMO-6-DEOXY-a-0-GLUCOPYRANOSIDE ... 

Hydroxyzine pamoate is designated chemically as l-(p-chlorobenzhydryl)4-[2-(2-hydroxyethoxy) ethyl] diethyl-enediamine salt of l.l -methylene bis (2 hydroxyl-naphthalene carboxylic acid). Hydroxyzine pamoate 25 mg/5... 

Walther et al. improved the Na0Ph/C02 system by tuning the role of the solvent, such that the carboxylation of acetone was carried out selectively by sodium phenoxide with N-methyl-caprolactam under 0.1 MPa C02 to afford 3-ketoglutaric acid in 65% yield [34]. The same authors reported the conversion of acetyl-naphthalene (acetonaphthone) to acetyl-naphthalene carboxylic acid with 84% yield, and of cyclohexanone to cyclohexane-2,6-dicarboxylic acid in 56% yield. 

Methoxy-7-methoxycarbony1-1,2, 3,4-tet rahydronaphthalene 2-Naphthalene-carboxylic acid, 5,6,7,8-tetrahydro-3-methoxy-, methyl ester (10) ... 

In a stndy of retention of aromatic carboxylic acids under IPC conditions, linear free energy relationships were observed between the capacity factors and the extraction eqnilibrinm constants of benzoic acid and naphthalene carboxylic acid. The capacity factor of benzene polycarboxylic acids was directly related to then-association constants and qnatemary ammonium ions calculated on the basis of an electrostatic interaction model [27,28],... 

Oxidative degradation of ancistrocladine (1) with KMn04 to the naphthalene carboxylic ester 2, which was independently synthesized, accounted for more than half of the carbon atoms of the molecule and simultaneously demonstrated the site of the linkage to the other molecular moiety. The structure and substitution pattern of the tetrahydro isoquinoline part of 1 became evident mainly from degradation products like the 7-lactone 7, the fully aromatic isoquinoline 4, as well as the benzofurane 9 (see Scheme 2), obtained by a Claisen rearrangement... 

In the naphthalene carboxylic acid series [structure type II, aromatic B, D, and E rings, no C ring], incorporation of a methyl group para to C-6 or at C-19 does not result in a significant loss of activity. However, incorporation of a methyl group at C-10 results in loss of activity. 

Nevertheless, using the 1,8-ANS (5) method, with ANS as a guest, fluorescence increases with 10 and 11 and therefrom complex formation constants have been obtained, which are remarkably higher than that of the cyclodextrins and of open chained reference host compounds. The complex constants of 10 towards the hydroxy-naphthalene carboxylates 13 and 14 as guests have also been determined The authors suppose the intermediate formation of inclusion complexes also because of the capability of 10 and especially 12 to accelerate the hydrolysis of chloroacetic acid phenolates in water solution. The increase of the hydrolysis rate is explained by the activation of the complexed esters. 

Reaction between full (2,3-2-0-acetyl-6-deoxy-6-iodine)-/3-CD and 6-hydroxy-2-naphthalene carboxylic acid methyl ester could generate the whole (2,3-di-0-acetyl-6-0-2-naphthyl methyl)-/S-CD in the NaH/DMF solution [10]. 

Polymeric structures based on networks of homoleptic eight-coordinate La(III) centers linked through 2,2 -bipyridine-A/ 77 -dioxide have been prepared, for example, by the reaction of La(CF3S03)3 and 2,2 - and 4,4 -bipyridine-A(A/ -dioxide in methanol at 20 °C [122]. The reaction of FeCl2, 1,10-phenanthroline and benzene-1,2,4,5-tetracarboxylate in water at 160 °C in a Teflon reactor produces a two-dimensional polymeric structure of [Fe(phenanthroline)-(benzenecarboxylate)] [123]. Multi-dimensional metalorganic coordination polymers with metal-aromatic interaction which exhibit strong photoluminescent behavior have been prepared by different Ag(I)-naphthalene-carboxylates with hexamethylenetetramine in CH2CI2 [124]. 

Amino-2-naphthalene-carboxylic acid 3-Amino-2-naphthoic acid C HgNOj 5959-52-4 187.195 ye If (dil al) 216.5 s EtOH, eth... 

A suitable substitution of the aromatic nucleus of benzoyl chloride (nitration, bromination), or the use of chlorides of naphthalene-carboxylic adds, or, especially, anthraquinone-carboxylic acids, results in their esters being solid substances, even when prepared from aliphatic alcohols. The most popular derivatives for the identification of alcohols are, however, the esters of 3,5-dinitrobenzoic acid. 

A final synthetic effort in the yohimbine alkaloid area concerns the studies reported by Loewenthal and his coworkers (Scheme 3.92) (143). The aim was to develop an efficient method to prepare the bicyclic enone 21, which serves as a key intermediate in the Woodward reserpine synthesis strategy (19). The route for preparation of 21 began with Friedel Crafts reaction of 2-methoxynaphthalene (523) with the oxalyl chloride equivalent 524, a process which afforded the acenaphthenoquinone 525. Oxidative-decarboxylation of 525 yielded the naphthalene-carboxylic acid 526 which was transformed by Birch reduction and esterification to the dihydro-derivative 527. Carboxyla-tion then provided geminal diester 528 which was epoxidized. Sequential lactonization and methylation afforded tricyclic lactone 529. Ester cleavage with subsequent decarboxylation gave lactone 530 which was demethylated to provide 531. While no further effort was given to the development of this... 

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