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Anthranilic Acid

Catalog No.: GC41593

Anthranilic Acid is a potential precursor in the synthesis of quinazolinones, including methaqualone.

Anthranilic Acid Chemical Structure

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Anthranilic Acid is a potential precursor in the synthesis of quinazolinones, including methaqualone.[1] For this reason, anthranilic acid, its esters, and its salts are categorized as List I chemicals with the Drug Enforcement Administration in the United States. Anthranilic acid is also a natural antimicrobial metabolite produced by a number of bacterial strains.[2] This product is intended for research and forensic applications.

[1]. Soliman, F.S., Shafik, R.M., and Elnenaey, E.A. Synthesis of methaqualone and its diphasic titration in pure and tablet forms. Journal of Pharmaceutical Sciences 67(3), 411-413 (1978).
[2]. Hund, H.K., de Beyer, A., and Lingens, F. Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp. Biological Chemistry of Hoppe-Seyler 371(10), 1005-1008 (1990).

Chemical Properties

Cas No. 118-92-3 SDF
Synonyms NSC 144, NSC 40929
Chemical Name 2-amino-benzoic acid
Canonical SMILES OC(C1=C(N)C=CC=C1)=O
Formula C7H7NO2 M.Wt 137.1
Solubility DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 0.5 mg/ml Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

Medicinal chemistry of Anthranilic Acid derivatives: A mini review

Drug Dev Res 2021 Nov;82(7):945-958.PMID:34117784DOI:10.1002/ddr.21842.

Anthranilic Acid and its analogues present a privileged profile as pharmacophores for the rational development of pharmaceuticals deliberated for managing the pathophysiology and pathogenesis of various diseases. The substitution on Anthranilic Acid scaffold provides large compound libraries, which enable a comprehensive assessment of the structure activity relationship (SAR) analysis for the identification of hits and leads in a typical drug development paradigm. Besides, their widespread applications as anti-inflammatory fenamates, the amide and anilide derivatives of Anthranilic Acid analogues play a central role in the management of several metabolic disorders. In addition, these derivatives of Anthranilic Acid exhibit interesting antimicrobial, antiviral and insecticidal properties, whereas the derivatives based on anthranilic diamide scaffold present applications as P-glycoprotein inhibitors for managing the drug resistance in cancer cells. In addition, the Anthranilic Acid derivatives serve as the inducers of apoptosis, inhibitors of hedgehog signaling pathway, inhibitors of mitogen activated protein kinase pathway, and the inhibitors of aldo-keto reductase enzymes. The antiviral derivatives of Anthranilic Acid focus on the inhibition of hepatitis C virus NS5B polymerase to manifest considerable antiviral properties. The Anthranilic Acid derivatives reportedly present neuroprotective applications by downregulating the key pathways responsible for the manifestation of neuropathological features and neurodegeneration. Nevertheless, the transition metal complexes of Anthranilic Acid derivatives offer therapeutic applications in diabetes mellitus, and obesity by regulating the activity of α-glucosidase. The present review demonstrates a critical analysis of the therapeutic profile of the key derivatives of Anthranilic Acid and its analogues for the rational development of pharmaceuticals and therapeutic molecules.

An anthranilic acid-responsive transcriptional regulator controls the physiology and pathogenicity of Ralstonia solanacearum

PLoS Pathog 2022 May 26;18(5):e1010562.PMID:35617422DOI:10.1371/journal.ppat.1010562.

Quorum sensing (QS) is widely employed by bacterial cells to control gene expression in a cell density-dependent manner. A previous study revealed that Anthranilic Acid from Ralstonia solanacearum plays a vital role in regulating the physiology and pathogenicity of R. solanacearum. We reported here that Anthranilic Acid controls the important biological functions and virulence of R. solanacearum through the receptor protein RaaR, which contains helix-turn-helix (HTH) and LysR substrate binding (LysR_substrate) domains. RaaR regulates the same processes as Anthranilic Acid, and both are present in various bacterial species. In addition, anthranilic acid-deficient mutant phenotypes were rescued by in trans expression of RaaR. Intriguingly, we found that Anthranilic Acid binds to the LysR_substrate domain of RaaR with high affinity, induces allosteric conformational changes, and then enhances the binding of RaaR to the promoter DNA regions of target genes. These findings indicate that the components of the Anthranilic Acid signaling system are distinguished from those of the typical QS systems. Together, our work presents a unique and widely conserved signaling system that might be an important new type of cell-to-cell communication system in bacteria.

Nematicidal Anthranilic Acid derivatives from Laccaria species

Phytochemistry 2019 Apr;160:85-91.PMID:30802801DOI:10.1016/j.phytochem.2019.01.008.

Three undescribed natural products, the Anthranilic Acid derivatives laccanthrilic acids A, B, and C, as well as the known (3S)-1,2,3,4-tetrahydro-3-β-carboline-3-carboxylic acid were isolated from fruiting bodies of Laccaria laccata. The structures were established by 1D and 2D NMR spectroscopy, HR-(+)-ESIMS and chemical synthesis. The absolute configuration of laccanthrilic acids A and B was determined by GC-MS after hydrolytic cleavage and derivatisation of the resulting glutamic acid with methanol and Mosher's reagent and subsequent comparison with authentic synthetic samples of known absolute configuration. The absolute configuration of laccanthrilic acid C was determined by comparison of the CD spectra of laccanthrilic acids B and C with each other. Metabolic profiling of related species showed that the compounds are common in the genus Laccaria. Laccanthrilic acid B exhibited moderate nematicidal effects against Caenorhabditis elegans, which might explain to some degree the beneficial role of these fungi for the growth and survival of their host plants.

Anthranilic Acid Accumulation in Saccharomyces cerevisiae Induced by Expression of a Nonribosomal Peptide Synthetase Gene from Paecilomyces cinnamomeus BCC 9616

Chembiochem 2022 Dec 16;23(24):e202200573.PMID:36250803DOI:10.1002/cbic.202200573.

Heterologous expression of nrps33, a nonribosomal peptide synthetase gene, from Paecilomyces cinnamomeus BCC 9616 in Saccharomyces cerevisiae unexpectedly resulted in the accumulation of Anthranilic Acid, an intermediate in tryptophan biosynthesis. Based on transcriptomic and real-time quantitative polymerase chain reaction (RT-qPCR) results, expression of nrps33 affected the transcription of tryptophan biosynthesis genes especially TRP1 which is also the selectable auxotrophic marker for the expression vector used in this work. The product of nrps33 could inhibit the activity of Trp4 involved in the conversion of anthranilate to N-(5'-phosphoribosyl)anthranilate and therefore caused the accumulation of Anthranilic Acid. This accumulation could in turn result in down-regulation of downstream tryptophan biosynthesis genes. Anthranilic Acid is typically produced by chemical synthesis and has been used as a substrate for synthesising bioactive compounds including commercial drugs; our results could provide a new biological platform for production of this compound.

Anthranilic Acid from Ralstonia solanacearum plays dual roles in intraspecies signalling and inter-kingdom communication

ISME J 2020 Sep;14(9):2248-2260.PMID:32457502DOI:10.1038/s41396-020-0682-7.

Quorum sensing (QS) signals are widely utilized by bacteria to regulate biological functions in response to cell population density. Previous studies have demonstrated that Ralstonia solanacearum employs two different types of QS systems. We report here that Anthranilic Acid controls important biological functions and the production of QS signals in R. solanacearum. It was demonstrated that the biosynthesis of Anthranilic Acid is mainly performed by TrpEG. The accumulation of Anthranilic Acid and the transcription of trpEG occur in a cell density-dependent manner in R. solanacearum. Both the Anthranilic Acid and TrpEG homologues are conserved in various bacterial species. Moreover, we show that Sporisorium scitamineum sexual mating and hypha formation are strongly inhibited by the addition of exogenous Anthranilic Acid. Our results suggest that Anthranilic Acid is important for the physiology of bacteria in addition to its role in inter-kingdom communication.


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