52573-74-7

Usage

Uses

Used in Pharmaceutical Industry:
N1-ISOPROPYL-2-CYANOACETAMIDE is used as a building block for the creation of various drugs due to its versatile chemical structure. It serves as a key intermediate in the synthesis of pharmaceuticals, enabling the development of new and innovative medications.
Used in Agrochemical Production:
N1-ISOPROPYL-2-CYANOACETAMIDE is utilized in the production of agrochemicals, where it acts as a valuable intermediate in the synthesis of various agricultural chemicals. Its presence in these products helps to enhance their effectiveness and performance in crop protection and other agricultural applications.
Used in Fine Chemicals Industry:
N1-ISOPROPYL-2-CYANOACETAMIDE is also employed in the synthesis of fine chemicals, where its unique structure and properties contribute to the development of high-quality specialty chemicals for various applications, including research, manufacturing, and other industrial processes.

InChI:InChI=1/C6H10N2O/c1-5(2)8-6(9)3-4-7/h5H,3H2,1-2H3,(H,8,9)

Upstream product

• 75-31-0 isopropylamine 
• 105-56-6 ethyl 2-cyanoacetate 
• 105-34-0 methyl 2-cyanoacetate 
• 130750-34-4 5-(Bis-isopropylamino-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 

Downstream Products

• 457604-61-4 1-isopropyl-4-propyl-2,6-dioxo-1,2,3,6-tetrahydropyridine-3-carbonitrile 
• 457604-62-5 1,4-diisopropyl-2,6-dioxo-1,2,3,6-tetrahydropyridine-3-carbonitrile 
• 1018452-75-9 C₁₃H₁₅N₃OS 
• 1309764-29-1 C₂₀H₂₁FN₄O₃ 
• 1309764-22-4 C₂₀H₂₂N₄O₃ 
• 116314-68-2 N-Isopropyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide 
• 1307896-39-4 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-cyano-N-isopropylpropanamide 
• 1307895-82-4 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-cyano-N-isopropylacrylamide 

Relevant academic research and scientific papers

5-Aminothiophene-2,4-dicarboxamide analogues as hepatitis B virus capsid assembly effectors

Chronic hepatitis B virus (HBV) infection represents a major health threat. Current FDA-approved drugs do not cure HBV. Targeting HBV core protein (Cp) provides an attractive approach toward HBV inhibition and possibly infection cure. We have previously identified and characterized a 5-amino-3-methylthiophene-2,4-dicarboxamide (ATDC) compound as a structurally novel hit for capsid assembly effectors (CAEs). We report herein hit validation through studies on absorption, distribution, metabolism and excretion (ADME) properties and pharmacokinetics (PK), and hit optimization via analogue synthesis aiming to probe the structure-activity relationship (SAR) and structure-property relationship (SPR). In the end, these medicinal chemistry efforts led to the identification of multiple analogues strongly binding to Cp, potently inhibiting HBV replication in nanomolar range without cytotoxicity, and exhibiting good oral bioavailability (F). Two of our analogues, 19o (EC50 = 0.11 μM, CC50 > 100 μM, F = 25%) and 19k (EC50 = 0.31 μM, CC50 > 100 μM, F = 46%), displayed overall lead profiles superior to reported CAEs 7–10 used in our studies.

KINASE INHIBITORS

Methods of inhibiting kinases using kinase inhibitors having olefin moieties are disclosed.

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.

Enols of substituted cyanomalonamides

(Chemical Equation Presented) Twenty open-chain mono-, di-, and trialkyl and aryl-N-substituted cyanomalonamides R2R1NCOCH-(CN) CONHR3 were prepared. In solution, signals for both amide and a single enol are mostly observed, despite the potential for E and Z isomeric enols. The equilibrium (KEnol) values between the amides and the enols were determined in different solvents by NMR spectra. They decrease on increasing the polarity of the solvent in the order CDCl3 ～ C6D6 > THF-d8 (CD3)2CO > CD3CN > DMF-d7 > DMSO-d6. For the R1R2NCOCH(CN)CONHR3 system when R1 = R2 = H, Me or R1 = H, R2 = Me, K Enol for R3 follows the order: C6F5 > Ph ≥ An ≥ i-Pr ≥ t-Bu, and for R1, R2:H, H > Me, H > Me, Me in all solvents. A unique feature is the appreciable % enol in DMSO-d6 when R1 = R2 = H, in contrast with enol systems with other electron-withdrawing groups (EWGs). Calculations (B3LYP/6-31G**) corroborate the higher KEnol values for less alkyl-substituted systems, showing that in the most stable conformer when R1 = H, R2 = R3 = Me the N-hydrogens are closer to the CN group. The order of promoting substituents for enol of amide formation is CONH2 > CO2CH2CF3 > CO2Me > CONHMe. The solid-state structures of the isolated species, determined by X-ray crystallography, were either amides or enols, and a higher KEnol(CDCl3) value does not ensure a solid enol structure. In no system were both solid species isolated. The X-ray structures of the enols were temperature-dependent. In most cases, the difference between the O-H and O...H bond lengths at low temperature were appreciable, but they become closer at the higher temperature. Similar tendency for either the C=C/C-C or the C-O/C=O bonds was observed. This is ascribed to a hydrogen shift between two regioisomeric enols in an asymmetric double-well potential, which becomes faster at a higher temperature. Calculations show that the enol structures are nonsymmetrical, resembling the lower temperature structures, even when they are chemically symmetrical, but the energy differences between the two regioisomers are 1 kcal. The hydrogen bonds in the enol moiety are strong, with O...O distances 2.45 A, and are resonance-assisted hydrogen bonds. IR spectra in solution and the solid state qualitatively corroborate the NMR and X-ray structure determination.

A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1

The RNA polymerase holoenzyme is a proven target for antibacterial agents. A high-throughput screening program based on this enzyme from Staphylococcus aureus had previously identified a 2-ureidothiophene-3-carboxylate as a low micromolar inhibitor. An investigation of the relationships between the structures of this class of compounds and their inhibitory- and antibacterial activities is described here, leading to a set of potent RNA polymerase inhibitors with antibacterial activity. Characterization of this bioactivity, including studies of the mechanism of action, is provided, highlighting the power of the reverse chemical genetics approach in providing tools to inhibit the bacterial RNA polymerase.

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.

Synthesis of α-Cyano Carbonyl Compounds by Flash Vacuum Thermolysis of (Alkylamino)methylene Derivatives of Meldrum's Acid. Evidence for Facile 1,3-Shifts of Alkylamino and Alkylthio Groups in Imidoylketene Intermediates

The syntheses and flash vacuum thermolyses of 5--2,2-dimethyl-1,3-dioxane-4,6-diones (Meldrum's acid derivatives) 13a - i are described.Thermolysis of 13a as well as of ethyl 3-(tert-butylamino)acrylate (22) gives a tautomeric mixture of cyanoacetaldehyde (14) and 3-hydroxypropenenitrile (15).Thermolysis of 13b gives iminoacrolein 26 and not cyanoacetone (29).Thermolysis of 13c, d gives S-methyl cyanothioacetate (30), and 13f - h give cyanoacetamides 31 in high yields. 2-Cyanopent-4-enoic acid derivatives 32 are obtained from Meldrum's acids 13e, i.The results are discussed in terms of facile 1,3-shifts of methylthio and alkylamino groups in imidoylketenes, interconverting imidoylketenes and acylketene imines.

Isocyanoacylamides

Isocyanoacylamides have been found to inhibit the growth of broadleaf plants, espcially when applied as a post-emergent. At lower rates, the compounds of the invention are effective in regulating the growth of corn plants.