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Upstream product

• 89-95-2 2-methyl-benzyl alcohol 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 90-02-8 salicylaldehyde 
• 622-33-3 N-benzyloxyamine 
• 40138-16-7 2-formylbenzene boronic acid 
• 21013-96-7 (E)-2-hydroxylbenzaldehyde oxime 
• 100-44-7 benzyl chloride 
• 271-89-6 1-benzofurane 
• 37898-42-3 α-chloro-N-cyclohexyl-N-propionaldonitrone 

Downstream Products

• 1377291-10-5 2-(2,6-dinitro-4-(trifluoromethyl)phenoxy)benzaldehyde O-benzyl oxime 
• 937273-73-9 C₁₇H₁₇NO₃ 
• 273-53-0 benzoxazole 
• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 
• 100-51-6 benzyl alcohol 

Relevant academic research and scientific papers

Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry

The kinetic and thermodynamic selectivities of imine formation have been investigated for several dynamic covalent libraries of aldehydes and amines. Two systems were examined, involving the reaction of different types of primary amino groups (aliphatic amines, alkoxy-amines, hydrazides and hydrazines) with two types of aldehydes, sulfobenzaldehyde and pyridoxal phosphate in aqueous solution at different pD (5.0, 8.5, 11.4) on one hand, 2-pyridinecarboxaldehyde and salicylaldehyde in organic solvents on the other hand. The reactions were performed separately for given amine/aldehyde pairs as well as in competitive conditions between an aldehyde and a mixture of amines. In the latter case, the time evolution of the dynamic covalent libraries generated was followed, taking into consideration the operation of both kinetic and thermodynamic selectivities. The results showed that, in aqueous solution, the imine of the aliphatic amine was not stable, but oxime and hydrazone formed well in a pH dependent way. On the other hand, in organic solvents, the kinetic product was the imine derived from an aliphatic amine and the thermodynamic products were oxime and hydrazone. The insights gained from these experiments provide a basis for the implementation of imine formation in selective derivatization of mono-amines in mixtures as well as of polyfunctional compounds presenting different types of amino groups. They may in principle be extended to other dynamic covalent chemistry systems.

Synthesis of 4-(alkoxyamino)chroman-2-ones via 6-exo-trig cyclization of carbon-centered radicals into oxime ethers

[Figure not available: see fulltext.] 4-(Alkoxyamino)chroman-2-ones were synthesized via a 6-exo-trig cyclization of alkyl radicals obtained from α-bromoesters containing an oxime ether group. In the case of secondary bromides, the best results were achie

Boronic acids facilitate rapid oxime condensations at neutral pH

We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M-1

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.

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.

Scope of the radical addition-cyclization-elimination reaction of oxime ether towards the synthesis of tricyclic lactam derivatives

The synthesis of tricyclic lactam building blocks by the radical addition-cyclization-elimination (RACE) reaction is presented. A range of oxime ethers carrying unsaturated ester part have been tested for the radical reaction. A variety of substituents were incorporated around the aromatic backbones and their effect on the RACE reaction has been examined. In addition, the power of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of constrained analogue of methoctramine.

Synthesis and 5-HT2A, 5-HT1A and α1- binding affinities of 2-[2-hydroxy-3-(pyridin-3-yl-methyl)amino]-, 2-[2-hydroxy-3-(2-pyridin-2-yl-ethyl)amino]- and 2-[2-hydroxy-3-(4-N-methyl- piperazin-1-yl)-amino]propoxybenzaldehyde

Some oxime ether-substituted aryloxypropanolamines 3-5, structurally related to the active metabolite 2 of sarpogrelate 1, were synthesized and tested for their affinities at 5-HT2A and 5-HT1A serotoninergic receptors as well as at t

Intermolecular alkyl radical addition to the carbon-nitrogen double bond of oxime ethers and hydrazones

Intermolecular carbon radical addition to the carbon-nitrogen double bond of oxime ethers and hydrazones was studied. The reaction of unactivated aldoxime ethers proceeded smoothly in the presence of BF3·OEt2 to give the alkylated products in high yields via the free radical-mediated carbon- carbon bond-forming process.

REACTIONS OF VINYLNITROSONIUM IONS WITH SOME AROMATIC HETEROCYCLES - ELECTROPHILIC SUBSTITUTION VS CYCLOADDITION.

Reaction of N-cyclohexyl-N-propenyl-nitrosonium ion and N-cyclohexyl-N-ethenylnitrosonium ion with indole and N-methylindole resulted in electrophilic substitution while reaction of the former with skatole, benzothiophene and benzofuran resulted in cycloaddition.

Boron Chelates of Salicylaldoxime and Derivatives

Formation and structure of boron chelates of salicylaldoxime are studied with O-alkyloximes and O-acyloximes of salicylaldehyde.The six-membered ring chelates thus obtained are synthesized also by alkylation resp. acylation of the preformed salicylaldoxime boron chelates.Thermolysis of the difluoroboron or diphenylboron chelates gives fluoroboronic resp. phenylboronic acid derivatives of salicylaldoxime that are isolated as dimeric compounds. - Keywords: Boron chelates; Salicylaldoxime boronates; Salicylaldoxime, O-alkyloxime and O-acyloxime; 2-Aminobezaldoxim