319-24-4

Usage

Uses

Used in Pharmaceutical Research:
2-Amino-5-fluorobenzoic acid methyl ester is used as a key intermediate in the synthesis of new drugs, leveraging its fluorinated structure to enhance metabolic stability and bioavailability. Its incorporation into drug molecules can potentially improve their efficacy and pharmacokinetic properties.
Used in Agrochemical Development:
In the agrochemical industry, 2-Amino-5-fluorobenzoic acid methyl ester is utilized as a precursor for the development of novel agrochemicals. Its unique reactivity and molecular structure contribute to the creation of compounds with specific pesticidal or herbicidal activities, aiming to increase crop yields and protect plants from various pests and diseases.
Used in Organic Synthesis:
2-Amino-5-fluorobenzoic acid methyl ester serves as a valuable building block in organic synthesis, enabling the construction of a wide range of fluorinated aromatic compounds. Its reactivity allows for the formation of various molecular structures with potential applications in materials science, medicinal chemistry, and other fields.
Overall, the versatility and unique properties of 2-Amino-5-fluorobenzoic acid methyl ester make it a promising compound for various applications across different industries, particularly in the development of new drugs and agrochemicals, as well as in organic synthesis for creating novel molecules with specific biological activities.

InChI:InChI=1/C8F10/c9-3-1(7(13,14)15)4(10)6(12)5(11)2(3)8(16,17)18

Upstream product

• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 394-02-5 5-fluoro-2-nitrobenzoyl chloride 
• 446-08-2 2-amino-5-fluorobenzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 7296-64-2 β-D-galactopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 623-27-8 terephthalaldehyde, 
• 67-56-1 methanol 
• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 393-85-1 methyl 5-fluoro-2-nitrobenzoate 

Downstream Products

• 777096-81-8 methyl 5-fluoro-2-[(2-ethoxyacetyl)amino]benzoate 
• 168900-02-5 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione 
• 1228017-72-8 methyl 2-azido-5-fluorobenzoate 
• 869294-30-4 ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate 
• 1253196-55-2 methyl (Z)-2-[(3-(2-benzylphenyl)-3-oxoprop-1-en-1-yl)amino]-5-fluorobenzoate 
• 1388642-19-0 methyl 5-fluoro-2-{[(4-methylphenyl)sulfonyl]amino}benzoate 
• 877264-44-3 5-fluoro-2-iodobenzaldehyde 
• 1202897-48-0 methyl 3-fluoro-6-iodobenzoate 
• 877264-43-2 (5-fluoro-2-iodophenyl)methanol 
• 66949-81-3 9-chloro-7-fluoro-1,2,3,4-tetrahydro-acridine 

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.

A General Approach to Enzyme-Responsive Liposomes

Liposomes are effective nanocarriers due to their ability to deliver encapsulated drugs to diseased cells. Nevertheless, liposome delivery would be improved by enhancing the ability to control the release of contents at the target site. While various stimuli have been explored for triggering liposome release, enzymes provide excellent targets due to their common overexpression in diseased cells. We present a general approach to enzyme-responsive liposomes exploiting targets that are commonly aberrant in disease, including esterases, phosphatases, and β-galactosidases. Responsive lipids correlating with each enzyme family were designed and synthesized bearing an enzyme substrate moiety attached via a self-immolating linker to a non-bilayer lipid scaffold, such that enzymatic hydrolysis triggers lipid decomposition to disrupt membrane integrity and release contents. Liposome dye leakage assays demonstrated that each enzyme-responsive liposome yielded significant content release upon enzymatic treatment compared to minimal release in controls. Results also showed that fine-tuning liposome composition was critical for controlling release. DLS analysis showed particle size increases in the cases of esterase- and β-galactosidase-responsive lipids, supporting alterations to membrane properties. These results showcase an effective modular strategy that can be tailored to target different enzymes, providing a promising new avenue for advancing liposomal drug delivery.

Neuroprotective activity of different monosaccharide-modified gastrodin analogs

Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.

Discovery of VU6027459: A First-in-Class Selective and CNS Penetrant mGlu7Positive Allosteric Modulator Tool Compound

Herein, we report the discovery of the first selective and CNS penetrant mGlu7 PAM (VU6027459) derived from a "molecular switch"within a selective mGlu7 NAM chemotype. VU6027459 displayed CNS penetration in both mice (Kp = 2.74) and rats (Kp= 4.78), it was orally bioavailable in rats (%F = 69.5), and undesired activity at DAT was ablated.

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.

Functionalised bicyclic tetramates derived from cysteine as antibacterial agents

Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton.

Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates

An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Tandem C-O and C-N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

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.