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Relevant bibliographies by topics / Anthranilic acid derivatives

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Academic literature on the topic 'Anthranilic acid derivatives'

Author: Grafiati

Published: 5 June 2025

Last updated: 24 June 2025

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Journal articles on the topic "Anthranilic acid derivatives"

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Chandrashekhara, Kumar B* Arun A. Bhagwath Chandrashekar K. S. "Pharmaceutical Chemistry Of Anthranilic Acid Derivatives: A Brief Review." International Journal of Pharmaceutical Sciences 2, no. 7 (2024): 2143–74. https://doi.org/10.5281/zenodo.13131906.

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Anthranilic acid is a benzenoid compound that has adjacent active important two reactive groups namely carboxylic acid group (-COOH) and amino group (-NH<sub>2</sub>). Consequently fascinating anthranilic acid derivatives have been prepared through both the active functional groups.  The literature review reveals an experiential and holistic approach of various manufacturing procedures and skills used for the production of anthranilic acid analogues and anthranilic scaffold along with the biological activities of some of the promising derived anthranilic acid molecules.  Pharmacology of anthranilic acid derivatives has been reported as alpha-glucosidase inhibitors, urease suppressors, keto-aldo reductase undecaprenyl pyrophosphate synthase (UppS) suppressors, mitogen activated protein kinase (MAPK), COX(Cyclooxygenase) inhibitors The analogues of anthranilic acid have been reported as an excellent pharmaceutical aids  such as anticancer, antidiabetic, antiviral, anti-inflammatory, analgesic and antimicrobial agents. The present review unveils the importance of anthranilic scaffold as a beginning material for the development of potent drug for their various pharmacological activities.

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Cambie, RC, PI Higgs, PS Rutledge, and PD Woodgate. "Aryne Chemistry of Podocarpic Acid Derivatives." Australian Journal of Chemistry 47, no. 8 (1994): 1483. http://dx.doi.org/10.1071/ch9941483.

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The anthranilic acid (2), a key intermediate for the generation of an aryne at C13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. The amine was converted into the anthranilic acid by two separate routes: firstly by directed lithiation and trapping of the lithium species with a CO2 moiety, and secondly by oxidative cleavage of an isatin fused across positions 13 and 14.

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3

Qin, Jiang Jiang, Hui Zi Jin, Jian Jun Fu, et al. "Anthranilic acid derivatives from Inula japonica." Chinese Chemical Letters 19, no. 5 (2008): 556–58. http://dx.doi.org/10.1016/j.cclet.2008.03.026.

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Slobodianiuk, Oksana, Oleksandra Berezhnytska, Tetyana Kamens'ka, and Мария Русакова. "SYNTHESIS AND PROPERTIES OF NEW N-ACYL DERIVATIVES OF ANTHRANILIC ACID." Ukrainian Chemistry Journal 85, no. 4 (2019): 59–70. http://dx.doi.org/10.33609/0041-6045.85.4.2019.59-70.

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A series of N-acyl derivatives of anthranil (or o -aminobenzoic acid) was first synthesized, namely 2-(4-octylbenzamido)benzoic acid, 2-(4-(heptyloxy)- benzamido)benzoic acid, 2-(4-(heptylsulfanyl)benz-amido)benzoic acid. 2-(4-octylbenzamido)benzoic acid was synthesized in five stages of octylbenzene, by acylating chloride acid using a Friedie-Crafts reaction. 2-(4-(heptyloxy)benzamido)benzoic acid was prepared from the methyl ester of p-hydroxybenzoic acid which, at the first stage, was activated with 1-bromoheptane in acetonitrile with potassium carbonate and catalytic amount of sodium iodide at heating. After that, hydrolysis of the ester group by hydroxide in the methanol–water system was performed. Synthesis of 2-(4-(heptylsulfanyl)benzamido)benzoic acid was carried out from p-sulfanylbenzoic acid, which was activated with 1-bromoheptane, in a system of ethanol–water with sodium hydroxide. Chlorinated hydrides of acids were obtained by reaction of acids with chlorinated thionyl in benzene. Acylation of the tret-butyl ester of anthranilic acid with formed chlorohydrides was carried out in pyridine upon heating and in dichloromethane with triethylamine (as the base), and dimethylaminopyridine (catalyst).At the last stage of the synthesis of all derivatives, the hydrolysis of tret-butyl esters with trifluoroacetic acid in dichloromethane to the formation of terminal compounds took place.The composition and structure of the synthesized compounds were determined using NMR 1H, infrared spectroscopy. The shape and position of the bands in the IR absorption spectra of the synthesized anthranilic acid derivatives are shifted and splited in comparison with the parent acid due to the presence of a secondary amino group, an additional aromatic moiety, and a different nature of the substitutes in the para-position to the amino group. For all synthesized derivatives, the sensitivity of various morphological forms Candida albicans was determined. The influence of the test substances on the cells of the yeast fungus was determined for 24–48 hours using Saburo and Spider nutrient media with the addition of mannitol. Compared with the already known influence of anthranilic acid on Candida albicans cells grown in Saburo nutrient medium for 24 hours, the compounds studied were more effective at all stages of cultivation. It has been shown that the synthetic derivatives studied are more active with respect to the cells in the biofilm composition, which consists of the yeast-like form of Candida albicans, than those cells that form a hyphal type biofilm. The yeast-like form of the Candida albicans cell is susceptible to synthetic derivatives. It is shown that the level of sensitivity of compounds 1-3 is higher in 4-6 times compared with anthranilic acid. Glyphs have been found to be more susceptible to the effects of the compounds studied than Е yeast cells of Candida albicans

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5

Platten, Michael, Peggy P. Ho, Sawsan Youssef, et al. "Treatment of Autoimmune Neuroinflammation with a Synthetic Tryptophan Metabolite." Science 310, no. 5749 (2005): 850–55. http://dx.doi.org/10.1126/science.1117634.

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Local catabolism of the amino acid tryptophan (Trp) by indoleamine 2,3-dioxygenase (IDO) is considered an important mechanism of regulating T cell immunity. We show that IDO transcription was increased when myelin-specific T cells were stimulated with tolerogenic altered self-peptides. Catabolites of Trp suppressed proliferation of myelin-specific T cells and inhibited production of proinflammatory T helper–1 (TH1) cytokines. N-(3,4,-Dimethoxycinnamoyl) anthranilic acid (3,4-DAA), an orally active synthetic derivative of the Trp metabolite anthranilic acid, reversed paralysis in mice with experimental autoimmune encephalomyelitis, a model of multiple sclerosis (MS). Trp catabolites and their derivatives offer a new strategy for treating TH1-mediated autoimmune diseases such as MS.

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Schrey, Hedda, Freya Janina Müller, Philipp Harz, Zeljka Rupcic, Marc Stadler, and Peter Spiteller. "Nematicidal anthranilic acid derivatives from Laccaria species." Phytochemistry 160 (April 30, 2019): 85–91. https://doi.org/10.1016/j.phytochem.2019.01.008.

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Schrey, Hedda, Müller, Freya Janina, Harz, Philipp, Rupcic, Zeljka, Stadler, Marc, Spiteller, Peter (2019): Nematicidal anthranilic acid derivatives from Laccaria species. Phytochemistry 160: 85-91, DOI: 10.1016/j.phytochem.2019.01.008, URL: http://dx.doi.org/10.1016/j.phytochem.2019.01.008

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Schrey, Hedda, Freya Janina Müller, Philipp Harz, Zeljka Rupcic, Marc Stadler, and Peter Spiteller. "Nematicidal anthranilic acid derivatives from Laccaria species." Phytochemistry 160 (April 2019): 85–91. http://dx.doi.org/10.1016/j.phytochem.2019.01.008.

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8

Shou, Qingyao, Linda K. Banbury, Alan T. Maccarone, et al. "Antibacterial anthranilic acid derivatives from Geijera parviflora." Fitoterapia 93 (March 2014): 62–66. http://dx.doi.org/10.1016/j.fitote.2013.12.008.

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9

Shaw, Claire, Matthias Hess, and Bart C. Weimer. "Microbial-Derived Tryptophan Metabolites and Their Role in Neurological Disease: Anthranilic Acid and Anthranilic Acid Derivatives." Microorganisms 11, no. 7 (2023): 1825. http://dx.doi.org/10.3390/microorganisms11071825.

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The gut microbiome provides the host access to otherwise indigestible nutrients, which are often further metabolized by the microbiome into bioactive components. The gut microbiome can also shift the balance of host-produced compounds, which may alter host health. One precursor to bioactive metabolites is the essential aromatic amino acid tryptophan. Tryptophan is mostly shunted into the kynurenine pathway but is also the primary metabolite for serotonin production and the bacterial indole pathway. Balance between tryptophan-derived bioactive metabolites is crucial for neurological homeostasis and metabolic imbalance can trigger or exacerbate neurological diseases. Alzheimer’s, depression, and schizophrenia have been linked to diverging levels of tryptophan-derived anthranilic, kynurenic, and quinolinic acid. Anthranilic acid from collective microbiome metabolism plays a complex but important role in systemic host health. Although anthranilic acid and its metabolic products are of great importance for host–microbe interaction in neurological health, literature examining the mechanistic relationships between microbial production, host regulation, and neurological diseases is scarce and at times conflicting. This narrative review provides an overview of the current understanding of anthranilic acid’s role in neurological health and disease, with particular focus on the contribution of the gut microbiome, the gut–brain axis, and the involvement of the three major tryptophan pathways.

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Al-Zaydi, Khadijah M., Ebtisam A. Hafez, and Mohamed H. Elnagdi. "Studies with Functionally Substituted Heteroaromatics: A New Routes for Synthesis of Pyridazino[2,3-a] Quinazoline and Pyridazino-6-imine Derivatives." Journal of Chemical Research 2000, no. 4 (2000): 154–55. http://dx.doi.org/10.3184/030823400103166940.

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Dissertations / Theses on the topic "Anthranilic acid derivatives"

1

Wiklund, Per. "Synthesis of heterocycles from anthranilic acid and its derivatives /." Stockholm, 2004. http://diss.kib.ki.se/2004/91-7349-913-7/.

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2

Liu, Yi Ting, and 劉怡婷. "The Pharmacokinetics of Anti-inflammatory Anthranilic Acid Derivatives in Rats." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/39680594300339525197.

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碩士<br>長庚大學<br>中醫學系天然藥物<br>99<br>The anthranilic acid derivatives, DSM-RX 116 (Ethyl 2- (2- fluorobenzamido) benzoate), DSM-RX 78 (Methyl 2-(2-fluorobenzamido)benzoate), and their hydrolysis compound, SMP-3 (2-(2-fluorobenzamido)benzoic acid), were synthesized. In previous study, DSM-RX 78 and DSM-RX 116 showed inhibitory effects on fMLP-induced superoxide anion generation in neutrophil with IC50 value of 0.65 and 0.17 μM. Furthermore, i.v. administration of DSM-RX 78 and DSM-RX 116 in rats subjected to trauma - hemorrhagic (T/H) shock caused a significant improvement in multiple organ dysfunctions. In present study, the experimental of plasma concentrations and pharmacokinetic analysis of DSM-RX 116, DSM-RX 78 and SMP-3 were determined by HPLC analysis. The pharmacokinetics, distributions and toxicitys of intravenously (1.0 mg/kg) and oral (40.0 mg/kg) administered SMP-3、DSM-RX 116 and DSM-RX 78 were also determined in Sprague Dawley rats. The in vitro experiments showed that DSM-RX 116 and DSM-RX 78 will hydrolysis to SMP-3 by esterase, and the protein binding ratio of SMP-3 was 100%. In addition, the protein binding ratio of the hydrolysis product SMP-3 was up to 99%. Mean kinetic parameters of DSM-RX 116, DSM-RX 78 and SMP-3 via i.v. administration as follows: elimination half-life (t1/2) 8.98, 8.77 and 23.99 min; clearance (CL) 24.57, 22.31 and 2.24 mL/min/kg; AUC0- 41.76, 48.03 and 486.44 min∙mg/L. Since DSM-RX 116 and DSM-RX 78 were hydorlyzed to SMP-3 through oral administration, they with similar kinetic parameters in oral administration. The toxicity of SMP-3, DSM-RX 78 and DSM-RX 116, including cumulative dose (3 mg/kg/day for 7 days) and single dose (45 mg/kg/day), were evaluated using intravenously administration. In single dose experimental, the histology analysis showed there were no toxicity to heart, brain, kidney, and lung; but they may exhibit liver toxicity.

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Southern, Cathrine Ann. "Spectroscopy of anthranilic acid and its derivatives in a supersonic jet /." 2002. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&res_dat=xri:pqdiss&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&rft_dat=xri:pqdiss:3060268.

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Book chapters on the topic "Anthranilic acid derivatives"

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Kikelj, D. "From Anthranilic Acid Derivatives and Nitriles." In Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-016-00761.

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Kikelj, D. "From Anthranilic Acid Derivatives and Guanidine, Imidates, or Formimidamides." In Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-016-00760.

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Kikelj, D. "From Anthranilic Acid Derivatives and Cyanates, Thiocyanates, Urea, or Carbamates." In Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-016-00759.

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Kikelj, D. "From Anthranilic Acid Derivatives and Amides or Thioamides (Niementowski's Synthesis)." In Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-016-00762.

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Kikelj, D. "From Anthranilic Acid Derivatives and Other N—C Synthons (1,3,5-Triazine, Gold's Reagent, Activated Nitriles)." In Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-016-00763.

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Conference papers on the topic "Anthranilic acid derivatives"

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Kwon, IS, K. Kwak Jong Hwan, S. Pyo, AR Kim, and FJ Schmitz. "A New Anthranilic Acid Derivative from Oscarella stillans as Regulator of Inflammatory Cytokines in Macrophages." In GA 2017 – Book of Abstracts. Georg Thieme Verlag KG, 2017. http://dx.doi.org/10.1055/s-0037-1608162.

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