52493-35-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-CYANO-N-PROPYLACETAMIDE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic properties.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-CYANO-N-PROPYLACETAMIDE serves as a valuable building block, enabling the construction of a wide array of chemical compounds for various applications.
Used in Research Laboratories:
2-CYANO-N-PROPYLACETAMIDE is utilized in research settings as a compound of interest for studying its properties and potential reactions, furthering scientific understanding and innovation in chemical and pharmaceutical fields.
Used in the Production of Derivatives:
2-CYANO-N-PROPYLACETAMIDE is also used as a precursor for the production of various derivatives, expanding its applications across different industries that may benefit from the unique characteristics of these derived products.

InChI:InChI=1/C6H10N2O/c1-2-5-8-6(9)3-4-7/h2-3,5H2,1H3,(H,8,9)

Upstream product

• 107-10-8 propylamine 
• 105-34-0 methyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 107-91-5 cyanoacetic acid amide 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 23795-49-5 2-cyano-3-(4-chlorophenyl)-N-propylacrylamide 
• 23795-37-1 2-cyano-3-phenyl-N-propylacrylamide 
• 457604-60-3 1,4-dipropyl-2,6-dioxo-1,2,3,6-tetrahydropyridine-3-carbonitrile 
• 94341-89-6 N-n-propyl-4,6-dimethyl-3-cyano-2-pyridone 
• 1093862-99-7 (E)-N-propyl-2-cyano-2-[(2-fluorophenyl)hydrazono]acetamide 
• 1253049-53-4 (E)-N-propyl-2-cyano-2-[(2-bromophenyl)hydrazono]acetamide 
• 1589638-39-0 2-cyano-3-(2,4-dimethoxy-6-((E)-4-methoxystyryl)phenyl)-N-propylacrylamide 

Relevant academic research and scientific papers

Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines

A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC 50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach

Based on a known nanomolar Bcl-2 homology domain 3 (BH3) mimetic 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b] pyrrole-9-carbonitrile (S1, MW: 331), we applied a fragment-based approach to obtain BH3 mimetics with improved affinity and improved solubility in a water-ethanol (9:1) cosolvent. After the deconstruction of 1 (S1), we obtained fragment cyanoacetamide (4), which was determined to be a ligand efficiency (LE) hot part. After a rational optimization through fragment evolution beginning with fragment 4, a smaller Mcl-1 inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g, MW: 288) with a 6-fold increase in affinity compared to 1 was obtained, as predicted by our optimization curve and identified by Mcl-1 protein nuclear magnetic resonance (NMR).

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Development and SAR of functionally selective allosteric modulators of GABAA receptors

Positive modulators at the benzodiazepine site of α2- and α3-containing GABAA receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at α2-/α3-containing GABAA receptors and that show no functional activity at α1-containing GABA A receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the α2- and α3-containing GABAA receptors, while simultaneously neutral antagonists at α1-containing GABAA receptors, is described. Such functionally selective modulators of GABAA receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses.

Synthesis of substituted 3-cyano-2-pyridones: Part IV - Influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed synthesis of substituted 3-cyano-2-pyridones

Lipase from Candida rugosa has been used to study the influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed reaction of pyridone ring formation in water at 40°C. Starting with 1,3-diketones and cyanoacetamides and for comparison, the expected corresponding substituted 3-cyano-2-pyridones have been synthesized by chemical methods. Bulkier substitueras lower the initial reaction rate of the enzyme catalyzed reactions and consequently the yield of the corresponding pyridones. N-alkyl cyanoacetamides are more reactive in comparison to the corresponding 3-alkyl-2,4-pentanediones with respect to the obtained yields of the corresponding substituted 3-cyano-2-pyridones.

Small molecule inhibitors of dynamin I GTPase activity: Development of dimeric tyrphostins

Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a ìèpotent lead, 2-cyano-3-(3,4- dihydroxyphenyl)thioacrylamide (1, IC50 70 μM). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low μM potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 ± 0.6 μM), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 ± 0.2 μM), and the corresponding 3-methyl ether (11) (IC 50 = 9 ± 3 μM). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50's of 1.7 ± 0.2, 1.7 ± 0.2, and 5 ± 1 μM, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50's of 42 ± 3, 38 ± 2, and 61 ± 2 μM, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.

DIHYDROPYRIDINE DERIVATIVES FOR USE AS HUMAN NEUTROPHIL ELASTASE INHIBITORS

The invention relates to novel dihydropyridine derivatives, of Formula (I) processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction and heart failure development.

Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries

2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH-acidic carbonyl compounds, N,N-dimethylformamide dimethylacetal and methylene active nitriles, leads to 2-pyridones and fused analogues in moderate to good overall yields and high purities. The proposed mechanism of this novel multi-component reaction, structure elucidation of products and intermediates are discussed.

Green chemistry approaches to the Knoevenagel condensation: Comparison of ethanol, water and solvent free (dry grind) approaches

We report a comparative study of the Knoevenagel condensation with a variety of substituted benzaldehydes (17 examples) and cyanoamides (3 examples), using three different methodologies: (a) traditional ethanol reflux; (b) water reflux; and (c) solvent fr

Dimerization of merocyanine dyes. Structural and energetic characterization of dipolar dye aggregates and implications for nonlinear optical materials

Aggregation of polar merocyanine dyes has been identified as an important problem in the fabrication of organic materials for photonic applications. In this work, a series of merocyanine dyes is synthesized, and their aggregation is investigated by a combination of several experimental techniques to reveal structure-property relationships. These studies provide clear evidence for the formation of centrosymmetric dimers for all investigated merocyanines in concentrated solution and in the solid state. The thermodynamics of dimerization in liquid solution is studied by concentration-dependent permittivity measurements, UV-vis spectroscopy, and electrooptical absorption experiments. A centrosymmetric dimer structure with antiparallel ordering of the dipole moments is observed in solution by 2D NMR spectroscopy as well as in the solid state by x-ray crystallography and interpreted in terms of dipolar and π-π interactions. The optical properties of the dimer aggregates are satisfactorily explained by an excitonic coupling model. The effect of an external electric field on the dimerization equilibrium is considered and quantitatively determined by electrooptical absorption measurements. Implications of the observed findings on the design of nonlinear optical and photorefractive materials are discussed.