86505-94-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-AMINO-6-FLUOROBENZOATE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 2-AMINO-6-FLUOROBENZOATE is utilized as a building block in the production of pesticides, enhancing the effectiveness of these chemicals in agricultural applications.
Used in Fine Chemicals Industry:
METHYL 2-AMINO-6-FLUOROBENZOATE also serves as an ingredient in the manufacturing of other fine chemicals, where its unique structure and functional groups are leveraged to create specialty products for various applications.
As a white solid at room temperature, METHYL 2-AMINO-6-FLUOROBENZOATE requires careful storage and handling due to its potential reactivity and toxicity, ensuring safety in its diverse applications across industries.

InChI:InChI=1/C8H8FNO2/c1-12-8(11)7-5(9)3-2-4-6(7)10/h2-4H,10H2,1H3

Upstream product

• 1897-52-5 2,6 difluorobenzonitrile 
• 67-56-1 methanol 
• 78755-94-9 5-fluoro-2H-benzo[d][1,3]-oxazine-2,4(1H)-dione 
• 434-76-4 2-amino-6-fluorobenzoic acid 
• 74-88-4 methyl iodide 
• 212189-78-1 methyl 2-fluoro-3-nitrobenzoate 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 77326-36-4 2-amino-6-fluorobenzonitrile 

Downstream Products

• 120257-01-4 methyl 2-chlorosulfonyl-6-fluorobenzoate 
• 221285-25-2 (2-amino-6-fluorophenyl)methanol 
• 1246775-80-3 methyl 2-(benzylamino)-6-fluorobenzoate 

Relevant academic research and scientific papers

Discovery of β-Arrestin Biased, Orally Bioavailable, and CNS Penetrant Neurotensin Receptor 1 (NTR1) Allosteric Modulators

Neurotensin receptor 1 (NTR1) is a G protein coupled receptor that is widely expressed throughout the central nervous system where it acts as a neuromodulator. Neurotensin receptors have been implicated in a wide variety of CNS disorders, but despite extensive efforts to develop small molecule ligands there are few reports of such compounds. Herein we describe the optimization of a quinazoline based lead to give 18 (SBI-553), a potent and brain penetrant NTR1 allosteric modulator.

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.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of formula I : wherein c, R2, R3, R4, R5, R6, R7 and R8 are defined herein, are useful as inhibitors of HIV replication.

CONSTRAINED COMPOUNDS AS CGRP-RECEPTOR ANTAGONISTS

The invention encompasses constrained bicyclic and tricyclic CGRP-receptor antagonists, methods for identifying them, pharmaceutical compositions comprising them, and methods for their use in therapy for treatment of migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

Constrained compounds as CGRP-receptor antagonists

The invention encompasses constrained bicyclic and tricyclic CGRP-receptor antagonists, methods for identifying them, pharmaceutical compositions comprising them, and methods for their use in therapy for treatment of migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

2-Arylaminopyrimidine derivatives as PLK inhibitors

Anilino-pyrimidine and 1,2,4-triazine compounds (1) are new. Anilino-pyrimidine and 1,2,4-triazine compounds of formula (1), their tautomers, racemates, enantiomers and/or diastereomers and acid-addition salts are new. X : NR 1a>, O or S; Y : CH or N; Z : hydrogen, halo, (halo)1-3C alkyl, 2-3C alkenyl, 2-3C alkynyl, formyl, 1-3C (halo)alkylcarbonyl, 2-3C alkenyl-, 2-3C alkynyl-carbonyl or pseudohalo; A : (hetero)aryl group (i) or (ii); R a> - R f>e.g. hydrogen, halo or nitro; R 1> and R 1a>hydrogen or methyl; R 2>e.g. Cl, Br, I, OR 6>; R 3>e.g. -CONR 1>-L-Q 3-Q 4-R 9>, -NR 1>-CO-L-Q 3-Q 4-R 9>; R 4>e.g. OR 6>, COR 6>, CONR 6>R 7>, NR 6>R 7>, NR 6>COR 7>, NR 6>SO 2R 7>, N=CR 6>R 7>, SR 6>, SOR 6>, SO 2R 6>, SO 2NR 6>R 7> or pseudohalogen, or any of 1-8C alkyl, 2-10C alkenyl or alkynyl, 3-8C cycloalkyl, (hetero)aryl or heterocyclyl; R 5>hydrogen, halo, trifluoromethyl, 1-3C alkyl or OR 6>; R 6>, R 7>e.g. hydrogen or any of 1-5C alkyl, 2-5C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; L : e.g. bond or residue of 1-16C alkyl, 2-16C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; Q 3 and Q 4bond or a mono- or bi-cyclic heterocyclyl, optionally substituted by one or more of Me, Et, halo, amino, hydroxy or pseudohalo; R 9>as L but not a bond; and T : N, O or S. Full definitions are given in the DEFINITIONS (Full Definitions) field. [Image] [Image] ACTIVITY : Cytostatic; Antiinflammatory; Immunosuppressive; Virucide; Anti-HIV; Dermatological; Nootropic; Neuroprotective; Nephrotropic; Vulnerary; Antibacterial; Fungicide; Antiparasitic; Antipsoriatic; Osteopathic; Cardiovascular-Gen; Vasotropic; Gastrointestinal-Gen. MECHANISM OF ACTION : Kinase inhibitor; Polo-like kinase (PLK) inhibitor. In a trial, (1) was found to have EC 50 against recombinant human PLK1 of below 5, generally 1 mu M. No results for specific compounds were given.

Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples

The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.

4H-3,1-BENZOXAZIN-4-ONES AND RELATED COMPOUNDS AND USE AS ENZYME INHIBITORS

Novel 2-amino-4H-3,1-benzoxazin-4-ones represented by the formula wherein R 1, R 2, R 3 and X are defined herein are useful as enzyme inhibitors in animals.