3849-20-5

Usage

Uses

Used in Organic Synthesis:
2-Cyano-2-oximinoacetamide is used as a building block in organic synthesis for the preparation of a variety of compounds. Its unique structure allows it to be a versatile component in the creation of new chemical entities.
Used in Chemical Reactions:
In the realm of chemical reactions, 2-Cyano-2-oximinoacetamide serves as a reagent, particularly in the formation of heterocyclic compounds. Its participation in such reactions is valuable for the development of complex molecular structures.
Used in Pharmaceutical Research:
2-Cyano-2-oximinoacetamide is used as a subject of pharmaceutical research for its potential applications in medicine. It is being studied for its antibacterial and antiviral properties, which could lead to the development of new treatments for infectious diseases.
Used in the Chemical Industry:
Within the chemical industry, 2-Cyano-2-oximinoacetamide is utilized for its capacity to contribute to the synthesis of various chemical products, highlighting its importance in the development of new materials and compounds.
Safety Considerations:
It is important to handle and store 2-Cyano-2-oximinoacetamide with care due to its classification as a hazardous material. Contact with the skin and eyes may cause irritation, necessitating proper safety measures during its use and disposal.

InChI:InChI=1/C3H3N3O2/c4-1-2(6-8)3(5)7/h8H,(H2,5,7)/b6-2+

Upstream product

• 107-91-5 cyanoacetic acid amide 
• 64-17-5 ethanol 
• 97925-39-8 nitromalononitrile 

Downstream Products

• 6719-21-7 2-Amino-2-cyanoacetamide 
• 475-08-1 cyano-nitro-acetic acid amide 
• 57967-17-6 C₆H₉N₃O₂ 
• 57967-16-5 C₆H₉N₃O₂ 
• 57967-21-2 C₉H₁₃N₃O₂ 
• 57967-29-0 C₁₀H₈BrN₃O₂ 
• 57967-30-3 C₁₀H₈FN₃O₂ 
• 57967-31-4 Cyan(phenacyloxyimino)acetamid 
• 57967-33-6 C₁₂H₁₃N₃O₃ 
• 57967-34-7 C₁₁H₁₀BrN₃O₃ 
• 57967-32-5 C₁₁H₈ClN₃O₃ 
• 57967-28-9 2-Cyano-2-[(E)-2-cyano-benzyloxyimino]-acetamide 
• 14056-39-4 acetylaminocyanoacetamide 
• 31785-07-6 N₂-benzoyl-3-nitriloalaninamide 

Relevant academic research and scientific papers

The synthesis of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

The objective was to synthesize (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2- ethoxyiminoacetic acid (the side chain for Ceftaroline fosamil). Oximation and alkylation were used on cyanoacetamide to get 2-cyano-2-hydroxyiminoacetamide, which became 2-ethyoxyiminopropanedinitrile through reaction with phosphorus oxychloride, and then aminolysis to get 2-ethoxyiminopropanedinitrile, which became 2-ethoxyimion-2-(5-amino-1,2,4 thiadiazol-3-yl) acetonitrile by brominating and with KSCN, followed by hydrolysis to get (Z)-2-(5-Amino-1,2,4- thiadiazol-3-yl)-2-ethoxyiminoacetic acid.

Design, synthesis and biological evaluation of novel Pseudomonas aeruginosa DNA gyrase B inhibitors

In the present study, we attempted to develop a novel class of compounds active against Pseudomonas aeruginosa (Pa) by exploring the pharmaceutically well exploited enzyme targets. Since, lack of Pa gyrase B crystal structures, Thermus thermophilus gyrase B in complex with novobiocin (1KIJ) was used as template to generate model structure by performing homology modeling. Further the best model was validated and used for high-throughput virtual screening, docking and dynamics simulations using the in-house database for identification of Pa DNA gyrase B inhibitors. This study led to an identification of three lead molecules with IC50 values in range of 6.25–15.6 μM against Pa gyrase supercoiling assay. Lead-1 optimization and expansion resulted in 15 compounds. Among the synthesized compounds six compounds were shown good enzyme inhibition than Lead-1 (IC50 6.25 μM). Compound 13 emerged as the most potential compound exhibiting inhibition of Pa gyrase supercoiling with an IC50 of 2.2 μM; and in-vitro Pa activity with MIC of 8 μg/mL in presence of efflux pump inhibitor; hence could be further developed as novel inhibitor for Pa gyrase B.

Preparation method of 3-aminofurazan-4-methanamide

The invention discloses a preparation method of 3-aminofurazan-4-methanamide. The method comprises the following steps: cyanoacetamide is subjected to nitrosation and isomerization to prepare 2-oximido cyanoacetamide, 2-oximido cyanoacetamide and hydroxylamine hydrochloride and organic base are subjected to a reaction to prepare an amidoxime intermediate which is 2-oximido-3-amidoxime acetamide, and the 2-oximido-3-amidoxime acetamide is subjected to a closed loop reaction under effect of thionyl chloride to generate a target product 3-aminofurazan-4-methanamide. The method has the advantagesof simple process flow, easily available raw material, and high product yield, and is suitable for industrial product, and is the novel synthetic method for 3-aminofurazan-4-methanamide.

SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazo[1,2-b]pyridazine compounds, substituted imidazo[1,5-b]pyridazine compounds, related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,2-b]pyridazine compounds described herein include substituted imidazo[1,2-b]pyridazine-3-carboxamide compounds and variants thereof.

Synthesis process of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid

The invention relates to a synthesis process of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid. With cyanoacetamide serving as a starting material, 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid is obtained through a hydroxyl oximation reaction, a methylation reaction, a cyclization reaction, a nitrile hydrolysis reaction and the like. Particularly, due to the fact that hydroxyapatite is added in the fifth step to serve as a catalyst, the yield of the intermediate product 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetonitrile and the total yield of the final product 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid can be effectively increased, and compared with the total yield not exceeding 9% in the prior art, the total yield of the technical scheme reaches 13% or so and is substantially increased; cost is lowered; industrial large-scale application is facilitated.

GPR17-MODULATING COMPOUNDS, DIAGNOSTIC AND THERAPEUTIC USES THEREOF

Disclosed are compounds able to modulate the activity of the GPR17 receptor in a highly specific way, which are useful in the treatment and diagnosis of diseases or dysfunctions involving the activation of said receptor. In particular, the compounds according to the invention can be used for neuroprotective and/or reparatory purposes, in cerebral, cardiac and renal ischaemia, in cerebral trauma, in chronic neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), and in demyelinating diseases such as multiple sclerosis.

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.

GPR17-MODULATING COMPOUNDS, DIAGNOSTIC AND THERAPEUTIC USES THEREOF

Disclosed are compounds able to modulate the activity of the GPR17 receptor in a highly specific way, which are useful in the treatment and diagnosis of diseases or dysfunctions involving the activation of said receptor. In particular, the compounds accor

Cyanoacetamide-based oxime carbonates: An efficient, simple alternative for the introduction of Fmoc with minimal dipeptide formation

Nowadays, most peptides are chemically achieved by using the Fmoc/tBu protection strategy, due to its fully orthogonal character, mild temporary group removal and resin cleavage steps. However, its introduction into N-unprotected amino acids is not exempt of synthetic inconveniences, such as dipeptide formation. Lately, novel oxime carbonates were introduced in the arsenal of reagents for the introduction of Fmoc, presenting almost negligible percentage of side-products. Herein, an enforced version of this family of Fmoc-carbonates is presented, containing stable and highly acidic cyanoacetamide-based oximes as leaving group. Such reactive species, affordable in only two steps from simple, readily available starting materials, show unusual ability to obtain the corresponding Fmoc-protected residues in high yield and minimal impact of detrimental side-products, mainly Fmoc-dipeptides.

Co-ordination ability of amino acid oximes. Potentiometric, spectroscopic and structural studies of complexes of 2-cyano-2-(hydroxyimino)acetamide

X-Ray crystallographic and solution studies have revealed the first examples of complexes of Cu2+ and Ni2+ with an oxime derivative in which completely deprotonated ligand molecules bind in trans position because of the lack of a hydrogen bond between the hydroxyl oxygens which usually stabilises the cis positioning.