37673-10-2

Usage

Nitrile derivative

The compound contains a nitrile functional group (CN), which is a cyano group attached to an alkyl or aryl group.

Benzodioxole ring

The compound has a benzodioxole ring, which is a six-membered aromatic ring with two oxygen atoms attached to it.

Morpholine group

The compound has a morpholine group, which is a five-membered ring with four methylene groups and one nitrogen atom.

Acetonitrile functional group

The compound has an acetonitrile group (CH3CN), which is a cyano group attached to a methyl group.

Used as an intermediate

The compound is primarily used as an intermediate for the synthesis of other pharmaceuticals and organic compounds.

Potential applications in medicinal chemistry and drug development

Due to its unique structural features, the compound may have potential applications in the development of new drugs and therapies.

Solid at room temperature

The compound is a solid at room temperature, which affects its handling and storage.

Handled in a controlled laboratory environment

Due to its potential hazards and reactivity, the compound should be handled in a controlled laboratory environment with proper safety measures.

Upstream product

• 120-57-0 piperonal 
• 151-50-8 potassium cyanide 
• 35175-75-8 morpholinium perchlorate 
• 110-91-8 morpholine 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 143-33-9 sodium cyanide 

Downstream Products

• 6969-80-8 4-methoxy-6-(3',4'-(methylenedioxy)phenyl)-2H-pyran-2-one 
• 95849-35-7 2-(Benzo<1,2-d><1,3>dioxol-5-yl)-Δ¹-pyrrolin 
• 53970-04-0 1-(3,4-methylenedioxyphenyl)-2-(3',4',5'-trimethoxyphenyl)ethanone 
• 56221-42-2 1-(benzo[d][1,3]dioxol-5-yl)butane-1,3-dione 
• 436148-69-5 (4R,5S)-2-Benzo[1,3]dioxol-5-yl-4,5-bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-pentanenitrile 

Relevant academic research and scientific papers

Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever

Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like α-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained α-aminonitriles could be considered as AChEIs with micromolar IC 50 values ranging from 42.0 to 478.0 μM (10.3-124.0 μg/mL). Among this series, the best AChE inhibitor was the pyrrolidine α-aminonitrile 3 (IC50 = 42 μM), followed by the piperidine α-aminonitriles 2 and 6 (IC50 = 45 μM and IC50 = 51 μM, respectively), and the compound 7 (IC50 = 51 μM). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides.

Steric Inhibition of Synergistic Radical Stabilizing Effects

Equilibrium acidities in Me2SO for 14 α-N-morpholinyl-, 6 α-N-piperidinyl-, and 7 α-cyclohexylarylacetonitriles and the oxidation potentials of their conjugate bases have been determined.The increased pKHA values by about 2 units observed in these systems, relative to the corresponding arylacetonitriles, is ascribed to the presence of increased steric constraints in the anions.Hammett plots revealed larger ρ values than for arylacetonitriles (6-7 versus 5.5), pointing to an increased negative charge density on the benzylic carbon atoms in the anions.A plot of anion oxidation potentials, Eox(A-), versus pKHA for the α-N-morpholinylarylacetonitriles was linear with a slope near unity, showing that remote substituents for the most part have very little effect on radical stabilities.A 5 and 6 kcal/mol lowering of the BDE of the acidic C-H bond caused by replacing the cyclohexyl group in α-cyclohexylphenylacetonitrile by α-N-morpholinyl or N-piperidinyl groups, respectively, is attributed to the strong donor properties of these amino functions.The effects are only about one-third as large, however, as similar effects in R2NCH2COPh, where the steric effect of Ph is absent and a synergistic effect is believed to be operative.