4185-96-0

Usage

InChI:InChI=1/C7H5N3O/c8-5-7(10-11)6-3-1-2-4-9-6/h1-4,9H/b7-6+

Upstream product

• 2739-97-1 pyridine-2-acetonitrile 
• 151-50-8 potassium cyanide 
• 69716-28-5 2-pyridylhydroxyiminomethyl chloride 

Downstream Products

• 121168-93-2 N-(tosyloxy)picolinimidoyl cyanide 
• 1346257-81-5 (2,4-dinitrophenoxyimino)-2-pyridylacetonitrile 
• 79598-34-8 benzyloxycarbonylvaline hydroxyiminocyano-α-picoline ester 

Relevant academic research and scientific papers

Benzoheterocyclic Oxime Carbamates Active against Mycobacterium tuberculosis: Synthesis, Structure-Activity Relationship, Metabolism, and Biology Triaging

Screening of a library of small polar molecules against Mycobacterium tuberculosis (Mtb) led to the identification of a potent benzoheterocyclic oxime carbamate hit series. This series was subjected to medicinal chemistry progression underpinned by structure-activity relationship studies toward identifying a compound for proof-of-concept studies and defining a lead optimization strategy. Carbamate and free oxime frontrunner compounds with good stability in liver microsomes and no hERG channel inhibition liability were identified and evaluated in vivo for pharmacokinetic properties. Mtb-mediated permeation and metabolism studies revealed that the carbamates were acting as prodrugs. Toward mechanism of action elucidation, selected compounds were tested in biology triage assays to assess their activity against known promiscuous targets. Taken together, these data suggest a novel yet unknown mode of action for these antitubercular hits.

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

Abstract: Three oxyma sulfonate esters were prepared using dichloromethane-water (two-phase method) in the presence of sodium carbonate for scavenging HCl. The products were characterized by FT-IR, NMR (1H and 13C), UV-Vis spectra and elemental analysis. X-ray single crystal diffraction experiments proved the molecular structures of three esters. Their molecular structures were also calculated using DFT/B3LYP method. The optimized structures agreed well with the X-ray structures. Time-dependent density functional theory (TD-DFT) was used to assign the electronic absorption bands observed experimentally. Pyridine derivative showed two bands at shorter λ max compared to the others, both experimentally and theoretically. The NMR chemical shifts were computed for protons and carbons using GIAO method, which correlated well with the experimental data. Natural charges, dipole moments and chemical reactivity of these molecules, as well as their non-linear optical activity, were computed and compared. Graphical Abstract:: SYNOPSIS An eco-friendly method was used to synthesise three oxyma-sulfonate esters using two-phase (dichloromethane-water) method in presence of sodium carbonate for scavenging HCl. The oxyma sulfonate esters were characterized using different spectroscopic techniques (FT-IR, NMR, UV-Vis) as well as X-ray single crystal diffraction analysis. The electronic and spectroscopic properties of these esters were computed using DFT/B3LYP method[Figure not available: see fulltext.].

Synthesis, characterization and anti-proliferation activities of novel cyano oximino sulfonate esters

A series of novel cyano oximino sulfonate derivatives were prepared from the reaction of arylsulfonyl chloride with different cyanoacetamide-based oximes ranging from the simplest unsubstituted amide to analogues containing N-ethyl (mimicking the Oxyma template), N-piperidinyl and N-morpholinyl chains. In addition, the cyano oximes, N-hydroxybenzimidoyl cyanide and N-hydroxypicolinimidoyl cyanide were also used in the synthesis of the novel cyano oximino sulfonate derivatives. The structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, and elemental analysis. The preliminary bioassays showed that some of the title compounds, such as 2-oxo-2-(piperidin-1-yl)-N-(tosyloxy)acetimidoyl cyanide (TsPipOx), N-(tosyloxy)benzimidoyl cyanide (TsPhOX), N-(naphthalen-2-ylsulfonyloxy)-2-oxo- 2-(piperidin-1-yl)acetimidoyl cyanide (NpsPipOx), 2-amino-N-(naphthalen-2- ylsulfonyloxy)-2-oxoacetimidoyl cyanide (NpsAmOx), N-(naphthalen-2- ylsulfonyloxy)benzimidoyl cyanide (NpsPhCN), and N-(naphthalen-2-ylsulfonyloxy) picolinimidoyl cyanide (NpsPyCN), showed anti-proliferation effect on the mouse fibroblast L929. The calculated IC50-values were ranging between 36.5 μg/mL and 0.235 mg/mL. However the anti-proliferation effects seem to be cytostatic rather than cytotoxic. The compounds only minimize the growth activity without completely killing the cells.

New topologies in pentanuclear nickel/oximato clusters: Structural and magnetic characterization

In the present work, five new Ni5 clusters employing the versatile 2-pyridylcyanoxime ligand have been synthesized and chemically, structurally, and magnetically characterized. The crystallographic examination of these Ni5 clusters together with those already published in the literature, giving a total number of 14 complexes, exhibiting up to 8 different topologies for which the relationship between topology, reaction conditions and magnetic response has been analyzed. DC magnetic measurements were carried in the 300-2 K range for the new complexes and the analysis of the experimental data revealed an antiferromagnetic response for the oximato mediated interactions with a variety of ground states (S = 0, 1, 3) as function of the cluster topology.

Spectrophotometric determination of pKa's of 1-Hydroxybenzotriazole and oxime derivatives in 95% acetonitrile-water

1-hydroxybenzotriazole derivatives are used with carbodiimide as additives to generate active esters during peptide bond formation. They are also used as additives during the peptide bond formation. Dissociation constants of the 1-hdroxybenzotriazole (HOBt) and its derivatives, 1- hydroxy-6- chlorobenzotriazole, 1-hydroxy-6-trifluoromethylbenzotriazole, 1-hydroxy-6-nitrobenzotriazole were determined spectrophotometrically in 95% acetonitrile-water. In addition, 7-aza-1- hydroxybenzotriazole (7-HOAt) and 4-aza-1-hydroxybenzotriazole (4-HOAt) were also studied. Recently, oxyma was reported as a good replacement for the benzotriazole derivatives. As alcoholic components of active esters, the oximes seem to be good leaving groups. Therefore it was expected, that the strongly acidic and nucleophilic oximes, which possess electron-withdrawing groups in the molecule, are suitable as additives during the peptide bond formation. The dissociation constant of some oximes,such as diethyl 2-(hydroxyimino)malonate, ethyl 2-cyano-2-(hydroxyimino) acetate (oxyma), hydroxycarbonimidoyl dicyanide and N-hydroxypicolinimidoyl cyanide in 95% acetonitrile-water are reported.

COMU: A safer and more effective replacement for benzotriazole-based uronium coupling reagents

We describe a new family of uronium-type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative-especially ethyl 2-cy ano-2- (hydroxyimino) acet ate (Oxyma)-had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (COMU) performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. COMU also showed a less hazardous safety profile than the benzotriazolebased HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.