50413-30-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-methoxy-benzoic acid methyl ester is used as a precursor in the synthesis of various pharmaceuticals for its ability to be chemically modified and incorporated into the structure of different drugs. Its versatility allows for the development of new medications with potential therapeutic benefits.
Used in Dye Industry:
In the dye industry, 2-Amino-4-methoxy-benzoic acid methyl ester is used as a starting material for the production of various dyes. Its chemical properties enable the creation of a range of colors and hues, making it a valuable component in the formulation of dyes for different applications.
Used in Agrochemical Industry:
2-Amino-4-methoxy-benzoic acid methyl ester is utilized as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in the development of these products contributes to the enhancement of agricultural productivity and crop protection.
Used in Chemical Production:
As a versatile chemical compound, 2-Amino-4-methoxy-benzoic acid methyl ester is used in the production of various chemicals for different industries. Its ability to be modified and combined with other compounds makes it a valuable component in the synthesis of a wide range of chemical products.

InChI:InChI=1/C9H11NO3/c1-12-6-3-4-7(8(10)5-6)9(11)13-2/h3-5H,10H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 4294-95-5 4-methoxyanthranilic acid 
• 33844-21-2 2-nitro-4-methoxybenzoic acid 
• 52351-75-4 6-methoxyisatin 
• 201230-82-2 carbon monoxide 
• 153898-63-6 2-iodo-5-methoxyaniline 
• 536-90-3 m-Anisidine 
• 75-18-3 dimethylsulfide 
• 121-98-2 methyl 4-methoxybenzoate 
• 181871-73-8 methyl 4-methoxy-2-nitrobenzoate 
• 6966-87-6 2-(hydroxyimino)-N-(3-methoxyphenyl)acetamide 

Downstream Products

• 108489-18-5 N-(5-methoxy-2-methoxycarbonyl-phenyl)-succinamic acid 
• 16064-24-7 7-methoxyquinazoline-4(3H)-one 
• 93009-62-2 methyl 4-methoxy-2-((4-methylphenyl)sulfonamido)benzoate 
• 187601-84-9 8-methoxy-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one 
• 187601-82-7 8-methoxy-1-tosyl-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one 
• 200010-59-9 8-Methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4,5-dione 4-oxime 
• 200010-60-2 8-Methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4,5-dione 4-(O-methyl-oxime) 
• 200010-64-6 N-[8-Methoxy-5-oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl]-acetamide 
• 200010-58-8 ethyl 8-methoxy-5-oxo-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate 
• 200010-72-6 N-[8-Methoxy-5-oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl]-propionamide 
• 200010-62-4 3-[5-Hydroxy-8-methoxy-4-[(E)-methoxyimino]-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-propionic acid ethyl ester 
• 200010-61-3 [5-Hydroxy-8-methoxy-4-[(E)-methoxyimino]-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-propynoic acid ethyl ester 

Relevant academic research and scientific papers

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins

A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.

Alkynyl Benzoxazines and Dihydroquinazolines as Cysteine Targeting Covalent Warheads and Their Application in Identification of Selective Irreversible Kinase Inhibitors

With a resurgence in interest in covalent drugs, there is a need to identify new moieties capable of cysteine bond formation that are differentiated from commonly employed systems such as acrylamide. Herein, we report on the discovery of new alkynyl benzoxazine and dihydroquinazoline moieties capable of covalent reaction with cysteine. Their utility as alternative electrophilic warheads for chemical biological probes and drug molecules is demonstrated through site-selective protein modification and incorporation into kinase drug scaffolds. A potent covalent inhibitor of JAK3 kinase was identified with superior selectivity across the kinome and improvements in in vitro pharmacokinetic profile relative to the related acrylamide-based inhibitor. In addition, the use of a novel heterocycle as a cysteine reactive warhead is employed to target Cys788 in c-KIT, where acrylamide has previously failed to form covalent interactions. These new reactive and selective heterocyclic warheads supplement the current repertoire for cysteine covalent modification while avoiding some of the limitations generally associated with established moieties.

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Antituberculosis Activity of the Antimalaria Cytochrome bcc Oxidase Inhibitor SCR0911

The ability to respire and generate adenosine triphosphate (ATP) is essential for the physiology, persistence, and pathogenicity of Mycobacterium tuberculosis, which causes tuberculosis. By employing a lead repurposing strategy, the malarial cytochrome bc

HETEROCYCLIC ACYL HYDRAZONE LINKERS, METHODS AND USES THEREOF

The present application is directed to compounds of Formula (I): compounds of Formula (II): compounds of Formula (III): and compounds of Formula (IV): compositions comprising these compounds and their uses, for example as medicaments and /or diagnostics.

Pyridyl Radical Cation for C?H Amination of Arenes

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp2)?H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N?X pyridinium reagents mediated by visible light.

Development of Potent Inhibitors of Fatty Acid Amide Hydrolase Useful for the Treatment of Neuropathic Pain

The unique role of fatty acid amide hydrolase (FAAH) in terminating endocannabinoid (EC) signaling supports its relevance as a therapeutic target. Inhibition of EC metabolizing enzymes elicits indirect agonism of cannabinoid receptors (CBRs) and therapeutic efficacy devoid of psychotropic effects. Based on our previous ligands, and aiming at the discovery of new selective FAAH inhibitors, we developed a series of 12 new compounds characterized by functionalized tricyclic scaffolds. All the developed compounds display negligible activity on monoacylglycerol lipase (MAGL) and CBRs. The most potent FAAH inhibitors of the newly developed series, 6-oxo-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepin-9-yl-6-phenylhexylcarbamate (5 h) and 4-oxo-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepin-9-yl-(6-phenylhexyl)carbamate (5 i) (nanomolar FAAH inhibitors, the latter of which also shows micromolar affinity at the CB1R), were selected for further studies. Results of cell-based studies on a neuroblastoma cell line (IMR32) demonstrated 5 h, 5 i, and our reference compound 3 ([3-(3-carbamoylpyrrol-1-yl)phenyl] N-(5-phenylpentyl)carbamate) to lack any cytotoxic effect, while all three showed the ability to decrease oxidative stress by reducing the expression of the redox-sensitive transcription factor NF-κB. Encouraged by these data, these compounds were studied in vivo and were dosed orally in a mouse model of neuropathic pain. At 10 mg kg?1 all the compounds were able to relieve the hypersensitivity induced by oxaliplatin.

Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR α/β agonist activity and equal PPAR-γ agonist activity than does bavachinin.

Discovery of novel bacterial RNA polymerase inhibitors: Pharmacophore-based virtual screening and hit optimization

The bacterial RNA polymerase (RNAP) is a validated target for broad spectrum antibiotics. However, the efficiency of drugs is reduced by resistance. To discover novel RNAP inhibitors, a pharmacophore based on the alignment of described inhibitors was used for virtual screening. In an optimization process of hit compounds, novel derivatives with improved in vitro potency were discovered. Investigations concerning the molecular mechanism of RNAP inhibition reveal that they prevent the protein-protein interaction (PPI) between σ70 and the RNAP core enzyme. Besides of reducing RNA formation, the inhibitors were shown to interfere with bacterial lipid biosynthesis. The compounds were active against Gram-positive pathogens and revealed significantly lower resistance frequencies compared to clinically used rifampicin.

NEW ANTIVIRAL COMPOUNDS

The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.