55418-28-5

Usage

Chemical structure

A derivative of isoindoline-1,3-dione with a 2-(2-fluorobenzyloxy) group attached.

Physical form

White to off-white powder.

Uses

Organic synthesis and medicinal chemistry.

Potential applications

Building block for the synthesis of pharmaceuticals and agrochemicals.

Availability

Mainly used in research and development, not commonly found in commercial products.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 446-51-5 2-fluorobenzyl alcohol 
• 345-35-7 2-fluorobenzyl chloride 
• 17698-09-8 2-[(hydroxyamino)carbonyl]benzoic acid 
• 85-44-9 phthalic anhydride 

Downstream Products

• 55418-27-4 O-(2-fluorobenzyl)hydroxylamine 
• 215599-91-0 O-(2-fluorobenzyl)hydroxylamine hydrochloride 

Relevant academic research and scientific papers

Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid

Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.

N-(benzyloxy)-2-chloronicotinamide compound as well as preparation method and application thereof

The invention belongs to the technical field of chemical synthesis and medicine application, and particularly relates to preparation and application of an N-(benzyloxy)-2-chloronicotinamide compound. The preparation method comprises the following steps: reacting phthalic anhydride with hydroxylamine, then reacting with triethylamine for acidification to prepare N-hydroxyphthalimide, then carrying out substitution and hydrazinolysis, and finally reacting with dichloronicotinoyl chloride to prepare the N-(benzyloxy)-2-chloronicotinamide compound. The preparation method disclosed by the invention is simple and convenient to operate, the structure of the obtained product is confirmed by a nuclear magnetic hydrogen spectrum, herbicidal activity tests are carried out on the obtained 15 target products, and results show that all target compounds have an obvious inhibition effect on the seeds of the Agrostis matsumurae under the concentration of 1mM, and the inhibition effect reaches 100%; and along with the decrease of the concentration, even if the concentration reaches 100 [mu] M, the target compound can still show good herbicidal activity.

SUBSTITUTED 1-HYDROXY-PYRIDIN-2(1H)-ONES, AND METHODS OF MAKING AND USING SAME

The present invention includes novel substituted 1-hydroxy-pyridin-2(1H)-ones, which can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention inhibit HBV RNAse H activity.

Design, synthesis, molecular docking and biological evaluation of novel coumarin-oxime ether derivatives as COX-2 inhibitors

Coumarin-oxime ether derivatives (14-25) were synthesized by an efficient and straight forward procedure from the reaction of 3-acetyl coumarin (1) and o-substituted benzyl hydroxyl amines (2-13) in pyridinium p-toluenesulfonate/dichloromethane (PPTS/DCM)

O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.

Synthesis and Antimicrobial Activities of Oximes Derived from O- Benzylhydroxylamine as FabH Inhibitors

Forty-three oxime derivatives were synthesized by allowing O-benzylhydroxylamines to react with primary benzaldehydes or salicylaldehydes; these products were gauged as potential inhibitors of β-ketoacyl-(acyl-carrier-protein) synthaseIII (FabH). Among the 43 compounds, 38 are reported herein for the first time. These compounds were assayed for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Bacillus subtilis, Staphylococcus aureus, and Enterococcus faecalis. Compounds with prominent antibacterial activities were tested for their E. coli FabH inhibitory activities. 3-((2,4 Dichlorobenzyloxyimino) methyl) benzaldehyde O-2,4-dichlorobenzyl oxime (44) showed the best antibacterial activity, with minimum inhibitory concentrations of 3.13-6.25μgmL-1 against the tested bacterial strains, exhibiting the best E. coli FabH inhibitory activity, with an IC50 value of 1.7mM. Docking simulations were performed to position compound 44 into the E. coli FabH active site in order to determine the most probable binding conformation.

Synthesis, biological evaluation, and molecular docking studies of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives as novel antitubulin agents

A series of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives (1h-20h) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 2h showed the most potent activity in vitro, which inhibited the growth of MCF-7, Hep-G2 and A549 cell lines with IC50 values of 0.70 ± 0.05, 0.68 ± 0.02 and 0.86 ± 0.05 μM, respectively. Compound 2h also exhibited significant tubulin polymerization inhibitory activity (IC50 = 3.06 ± 0.05 μM). The result of flow cytometry (FCM) demonstrated that compound 2h induced cell apoptosis. Docking simulation was performed to insert compound 2h into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 2h with potent inhibitory activity in tumor growth may be a potential anticancer agent.

Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs

A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL -1. Compound 2a and 3a exhibited good activities against P. piricola at low dosage.

1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo.