Anthranilic Acid (anthranilic + acid)

Distribution by Scientific Domains


Selected Abstracts


ChemInform Abstract: Bacterial Translation Inhibitors, 1-Acylindazol-3-ols as Anthranilic Acid Mimics.

CHEMINFORM, Issue 14 2009
Donna L. Romero
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


Isoxazolinyl Derivatives of Anthranilic Acid as Antiinflammatory Agents.

CHEMINFORM, Issue 44 2003
Preeti Rani
Abstract For Abstract see ChemInform Abstract in Full Text. [source]


ChemInform Abstract: The Discovery of Anthranilic Acid-Based MMP Inhibitors.

CHEMINFORM, Issue 15 2001
Part 1.
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


ChemInform Abstract: Synthesis, Antiinflammatory and Analgesic Activity of Several Arylamides of N-Substituted Anthranilic Acids.

CHEMINFORM, Issue 34 2001
A. B. Shakirova
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


Acute action of rotenone on nigral dopaminergic neurons , involvement of reactive oxygen species and disruption of Ca2+ homeostasis

EUROPEAN JOURNAL OF NEUROSCIENCE, Issue 10 2009
Peter S. Freestone
Abstract Rotenone is a toxin used to generate animal models of Parkinson's disease; however, the mechanisms of toxicity in substantia nigra pars compacta (SNc) neurons have not been well characterized. We have investigated rotenone (0.05,1 ,m) effects on SNc neurons in acute rat midbrain slices, using whole-cell patch-clamp recording combined with microfluorometry. Rotenone evoked a tolbutamide-sensitive outward current (94 ± 15 pA) associated with increases in intracellular [Ca2+] ([Ca2+]i) (73.8 ± 7.7 nm) and intracellular [Na+] (3.1 ± 0.6 mm) (all with 1 ,m). The outward current was not affected by a high ATP level (10 mm) in the patch pipette but was decreased by Trolox. The [Ca2+]i rise was abolished by removing extracellular Ca2+, and attenuated by Trolox and a transient receptor potential M2 (TRPM2) channel blocker, N -(p -amylcinnamoyl) anthranilic acid. Other effects included mitochondrial depolarization (rhodamine-123) and increased mitochondrial reactive oxygen species (ROS) production (MitoSox), which was also abolished by Trolox. A low concentration of rotenone (5 nm) that, by itself, did not evoke a [Ca2+]i rise resulted in a large (46.6 ± 25.3 nm) Ca2+ response when baseline [Ca2+]i was increased by a ,priming' protocol that activated voltage-gated Ca2+ channels. There was also a positive correlation between ,naturally' occurring variations in baseline [Ca2+]i and the rotenone-induced [Ca2+]i rise. This correlation was not seen in non-dopaminergic neurons of the substantia nigra pars reticulata (SNr). Our results show that mitochondrial ROS production is a key element in the effect of rotenone on ATP-gated K+ channels and TRPM2-like channels in SNc neurons, and demonstrate, in these neurons (but not in the SNr), a large potentiation of rotenone-induced [Ca2+]i rise by a small increase in baseline [Ca2+]i. [source]


Altered kynurenine metabolism correlates with infarct volume in stroke

EUROPEAN JOURNAL OF NEUROSCIENCE, Issue 8 2007
L. G. Darlington
Abstract Inflammation and oxidative stress are involved in brain damage following stroke, and tryptophan oxidation along the kynurenine pathway contributes to the modulation of oxidative stress partly via the glutamate receptor agonist quinolinic acid and antagonist kynurenic acid, and via redox-active compounds such as 3-hydroxyanthranilic acid. We have confirmed that following a stroke, patients show early elevations of plasma neopterin, S100B and peroxidation markers, the latter two correlating with infarct volume assessed from computed tomography (CT) scans, and being consistent with a rapid inflammatory response. We now report that the kynurenine pathway of tryptophan metabolism was also activated, with an increased kynurenine : tryptophan ratio, but with a highly significant decrease in the ratio of 3-hydroxyanthranilic acid : anthranilic acid, which was strongly correlated with infarct volume. Levels of kynurenic acid were significantly raised in patients who died within 21 days compared with those who survived. The results suggest that increased tryptophan catabolism is initiated before or immediately after a stroke, and is related to the inflammatory response and oxidative stress, with a major change in 3-hydroxyanthranilic acid levels. Together with previous evidence that inhibiting the kynurenine pathway reduces brain damage in animal models of stroke and cerebral inflammation, and that increased kynurenine metabolism directly promotes oxidative stress, it is proposed that oxidative tryptophan metabolism may contribute to the oxidative stress and brain damage following stroke. Some form of anti-inflammatory intervention between the rise of S100B and the activation of microglia, including inhibition of the kynurenine pathway, may be valuable in modifying patient morbidity and mortality. [source]


Enhancement of Ca2+ -regulated exocytosis by indomethacin in guinea-pig antral mucous cells: arachidonic acid accumulation

EXPERIMENTAL PHYSIOLOGY, Issue 1 2006
Shoko Fujiwara
Ca2+ -regulated exocytosis is enhanced by an autocrine mechanism via the PGE2,cAMP pathway in antral mucous cells of guinea-pigs. The inhibition of the PGE2,cAMP pathway by H-89 (an inhibitor of protein kinase A, PKA) or aspirin (ASA, an inhibitor of cyclo-oxygenase, COX) decreased the frequency of ACh-stimulated exocytotic events by 60%. Indomethacin (IDM, an inhibitor of COX), however, decreased the frequency of ACh-stimulated exocytotic events only by 30%. Moreover, IDM increased the frequency of ACh-stimulated exocytotic events by 50% in H-89-treated or ASA-treated cells. IDM inhibits the synthesis of Prostaglandin (PGG/H) and (15R)-15-hydroxy-5,8,11 cis-13-trans-eicosatetraenoic acid (15R-HPETE), while ASA inhibits only the synthesis of PGG/H. Thus, IDM may accumulate arachidonic acid (AA). AACOCF3 or N -(p -amylcinnamoyl) anthranilic acid (ACA; both inhibitors of phospholipase A2, PLA2), which inhibits AA synthesis, decreased the frequency of ACh-stimulated exocytotic events by 60%. IDM, however, did not increase the frequency in AACOCF3 -treated cells. AA increased the frequency of ACh-stimulated exocytotic events in AACOCF3 - or ASA-treated cells, similar to IDM in ASA- and H-89-treated cells. Moreover, in the presence of AA, IDM did not increase the frequency of ACh-stimulated exocytotic events in ASA-treated cells. The PGE2 release from antral mucosa indicates that inhibition of PLA2 by ACA inhibits the AA accumulation in unstimulated and ACh-stimulated antral mucosa. The dose,response study of AA and IDM demonstrated that the concentration of intracellular AA accumulated by IDM is less than 100 nm. In conclusion, IDM modulates the ACh-stimulated exocytosis via AA accumulation in antral mucous cells. [source]


SnCl2 · 2H2O-catalyzed one-pot synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 2 2010
Min Wang
A simple, efficient, and green procedure for the one-pot synthesis of 4(3H)-quinazolinones by three components condensation of anthranilic acid, ortho esters, and amines in the presence of SnCl2 · 2H2O has been developed. The reaction occurred within short reaction time at room temperature under solvent-free conditions to afford the title products in excellent yields. J. Heterocyclic Chem., (2010). [source]


Simple synthesis of 2-amino-4-(het)aryl-4,6-dihydro-1(3)(11)H -[1,3,5]triazino[2,1- b]quinazolin-6-ones,

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 1 2008
Anton V. Dolzhenko
The 2-amino-4-(het)aryl-4,6-dihydro-1(3)(11)H -[1,3,5]triazino[2,1- b]quinazolin-6-ones were prepared readily by cyclocondensation of anthranilic acid derived 4-oxo-3,4-dihydroquinazolinyl-2-guanidine with a variety of aldehydes. The structures of the compounds were confirmed by nmr spectroscopy, including 2D NOESY experiments. [source]


pH sensor based on polyaniline and aniline,anthranilic acid copolymer films using quartz crystal microbalance and electronic absorption spectroscopy

POLYMERS FOR ADVANCED TECHNOLOGIES, Issue 8 2008
M. M. Ayad
Abstract The pH sensitivity based on conducting polyaniline (PANI) and copolymer of aniline and o -anthranilic acid (AA) films were studied using quartz crystal microbalance (QCM) technique and UV,Vis spectroscopy. The sensor was constructed from these polymer films coated on the electrode of the QCM. The resonant frequency changes as a function of pH in the range of 2,12 were measured. These changes are quantitative indication of the degree of dedoping or redoping of the polymer films upon the subsequent exposure of the electrode to 0.25,M sulfuric acid and different pH solutions. There are two linear regressions between the frequency change and pH with two different and opposite slopes in the regions from 2 to 9 and 9 to 12. The pH sensitivity of the copolymer film was found to be less than using the PANI film. Thin films of PANI and copolymer, which were chemically polymerized in a sulfuric acid solution, were deposited onto the inner walls of the quartz cuvettes. The UV,Vis absorption spectra of these films were measured in different pH solutions. Relations between the maximum absorption and its wavelength versus pH were constructed. The copolymer film shows some advantages over the PANI film. The difference between the PANI and copolymer films as pH sensors using the QCM and electronic absorption extends from the determination of pKa for both films. Copyright © 2008 John Wiley & Sons, Ltd. [source]


Toxicity and disruption of midgut physiology in larvae of the European corn borer, Ostrinia nubilalis, by anion transporter blockers

ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY (ELECTRONIC), Issue 3 2009
Dhana Raj Boina
Abstract In this study, four blockers of anion transporters (ATs) belonging to four different classes of organic acids, including DIDS (4, 4'-diisothiocyanatostilbene-2, 2'- disulfonic acid; a stilbene disulfonic acid), NPPB [(5-nitro-2-(3-phenylpropylamino) benzoic acid; an anthranilic acid)], 9-AC (anthracene-9-carboxylic acid; an aromatic carboxylic acid), and IAA-94 (indanyloxy acetic acid; an indanyloxy alkanoic acid), were tested for their toxicity against the European corn borer (ECB), Ostrinia nubilalis. All the AT blockers inhibited the growth of larvae, increased the developmental time, and decreased survival compared to controls, when second-instar ECB larvae were fed for seven days on treated diet. In general, DIDS and NPPB were the most active compounds, with the rank order of activity being DIDS>NPPB>IAA-94>9-AC. All the AT blockers decreased the midgut alkalinity in fifth-instar larvae when fed for 3,h on treated diet. Effective concentrations required for 50% decrease in midgut alkalinity (EC50) ranged between 29.1 and 41.2,ppm and the rank order of activity was NPPB>DIDS>IAA-94>9-AC. Similarly, all the tested AT blockers inhibited 36Cl, uptake from the midgut lumen in fifth-instar larvae when fed for 3,h on treated diet. Concentrations required for 50% inhibition of 36Cl, uptake (IC50) ranged between 7.4 and 11.0,ppm and the rank order of activity was DIDS>NPPB>9-AC >IAA-94. Modest to highly strong positive correlations observed among growth, midgut alkalinity, and midgut Cl, ion transport in AT blocker,fed larvae suggested that these effects are causally related to each other. Finally, AT blockers have the potential to become good candidates for development of insecticides with a unique mode of action. © 2009 Wiley Periodicals, Inc. [source]


N-[3,4-dimethoxycinnamoyl]-anthranilic acid (tranilast) suppresses microglial inducible nitric oxide synthase (iNOS) expression and activity induced by interferon-, (IFN-,)

BRITISH JOURNAL OF PHARMACOLOGY, Issue 6 2001
Michael Platten
Microglial cells up-regulate inducible nitric oxide synthase (iNOS) expression in response to various pro-inflammatory stimuli including interferon-, (IFN-,), allowing for the release of nitric oxide (NO). Tranilast (N-[3,4-dimethoxycinnamoyl]-anthranilic acid) is an antiallergic compound with suppressive effects on the activation of monocytes. Here, we show that N9 murine microglial cells express iNOS mRNA and protein and release nitric oxide into the culture medium in response to IFN-, (200 u ml,1) as measured by Northern and Western blot analyses and Griess assay. Exposure to non-toxic doses of tranilast (30 , 300 ,M) leads to a concentration-dependent inhibition of IFN-,-induced (200 u ml,1) iNOS mRNA and protein expression. This is paralleled by a suppression of NO-release into the cell culture medium. Inhibition of IFN-,-induced iNOS mRNA expression by tranilast is paralleled by an inhibition of nuclear factor-,B (NF-,B) activation and phosphorylation of inhibitory ,B (I,B) as determined by Western blot analyses and NF-,B reporter gene assay. These results suggest that tranilast-mediated suppression of microglial iNOS activity induced by IFN-, involves the inhibition of NF-,B-dependent iNOS mRNA expression. British Journal of Pharmacology (2001) 134, 1279,1284; doi:10.1038/sj.bjp.0704373 [source]


Disubstituted 4(3H) Quinazolones: A Novel Class of Antitumor Agents

CHEMICAL BIOLOGY & DRUG DESIGN, Issue 3 2009
Vikas Srivastava
A series of disubstituted 4(3H) quinazolines were designed for potential application in tumors. Firstly, N -benzoyl anthranilic acid is formed, which undergoes cyclization in the presence of pyridine. Subsequently, nucleophilic attack by semicarbazide on the carbonyl carbon gives 2-substituted 3-carbamido 4(3H) quinazolones, which gives final compound with appropriate substitution. The final as well as intermediate products were confirmed by NMR, FT-IR, and mass spectrometry. In vitro toxicity was performed with different cell lines and showed that the connection of hydrophilic styryl to quinazoline moiety increases its efficacy. [source]


KYNURENINE PATHWAY METABOLISM IN PATIENTS WITH OSTEOPOROSIS AFTER 2 YEARS OF DRUG TREATMENT

CLINICAL AND EXPERIMENTAL PHARMACOLOGY AND PHYSIOLOGY, Issue 11 2006
Caroline M Forrest
ABSTRACT 1Metabolism of tryptophan along the oxidative pathway via kynurenine results in the production of quinolinic acid and kynurenic acid, which can act on glutamate receptors in peripheral tissues. We have now measured the concentrations of kynurenine pathway metabolites in the plasma of patients with osteoporosis before treatment with drugs, throughout and after 2 years of treatment with the drugs raloxifene or etidronate. Oxidative stress was assessed by measuring levels of the lipid peroxidation products malondialdehyde and 4-hydroxynonenal. Kynurenines were analysed by HPLC. Bone density was measured using dual-energy X-ray absorptiometry scans. 2Patients with osteoporosis showed significantly lower baseline levels of 3-hydroxyanthranilic acid compared with healthy controls, but significantly higher levels of anthranilic acid and lipid peroxidation products. After 2 years treatment with etidronate and calcium, we observed significant therapeutic responses quantified by bone densitometric scanning. Significant improvements were not seen in patients treated with raloxifene. 3In parallel, the levels of 3-hydroxyanthranilic acid, anthranilic acid and lipid peroxidation products were restored to control values by both drug treatments studied and tryptophan levels were increased significantly compared with baseline values. 4The results suggest that tryptophan metabolism is altered in osteoporosis in a manner that could contribute to the oxidative stress and, thus, to progress of the disease. The oxidative metabolism of tryptophan (the kynurenine pathway) could represent a novel target for the development of new drugs for the treatment of osteoporosis. In addition, we noted that etidronate is a more effective drug than raloxifene, but that the simultaneous use of non-steroidal anti-inflammatory drugs may reduce the efficacy of etidronate. [source]


The reaction of acetic acid 2-selenoxo-2H -pyridin-1-yl esters with benzynes: A convenient route to Benzo[b]seleno[2,3- b]pyridines

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 1 2004
U. Narasimha Rao
Benzyne and its 3,4,5,6-tetraphenyl, 3- and 4-methyl, 3-methoxy and 4,5-difluoro derivatives react with acetic acid 2-selenoxo-2H -pyridin-1-yl esters 4a-e to give benzo[b]seleno[2,3- b]pyridines 10,15 in modest yields. The benzynes were generated by one or more of the following methods: diazotization of anthranilic acids 5a-g with isoamyl nitrate; mild thermal decomposition of 2-diazoniobenzenecarboxylate hydrochlorides 6a-d treatment of (phenyl)[o -(trimethylsilyl)phenyl]iodonium triflate (7) with tetrabutylammonium fluoride; and treatment of 2-trimethylsilylphenyl triflates 8a-c with cesium fluoride. In all the reactions, the corresponding 2-(methylselenenyl)pyridines 16a-d were also obtained suggesting that these reactions may involve selenium addition to benzyne via a SET (single electron transfer). [source]