3741-87-5

Usage

General Description

1-methyl-1-phenyl-2-(1-phenylethylidene)hydrazine, also known as phenelzine, is a hydrazine derivative that is used as a monoamine oxidase inhibitor (MAOI) antidepressant. It works by blocking the enzymes that break down certain neurotransmitters in the brain, leading to an increase in their levels. This, in turn, helps to alleviate the symptoms of depression. Phenelzine has been shown to be effective in treating major depressive disorder and other mood disorders. However, it is also associated with potential side effects and drug interactions, and therefore should be used with caution and under the supervision of a healthcare professional.

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 98-86-2 acetophenone 
• 651712-40-2 acetophenone phenylhydrazone 
• 74-88-4 methyl iodide 
• 536-74-3 phenylacetylene 
• 100-63-0 phenylhydrazine 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 

Downstream Products

• 106032-47-7 1-(Methyl-phenyl-amino)-6-phenyl-2,3-dihydro-1H-pyridin-4-one 
• 10604-22-5 3-phenylcinnoline 
• 109310-82-9 2-(N-methyl-N-phenylhydrazono)-2-phenylacetaldehyde 
• 167895-49-0 (C₆H₅C(CH₂)NN(CH₃)(C₆H₅))PdCl(P(C₆H₅)3) 
• 128737-90-6 2,4,7-Trinitro-fluoren-9-one; compound with N-methyl-N-phenyl-N'-[1-phenyl-eth-(E)-ylidene]-hydrazine 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

Zirconium complexes stabilized by amine-bridged bis(phenolato) ligands as precatalysts for intermolecular hydroamination reactions

A series of zirconium complexes bearing amine-bridged bis(phenolato) ligands of different steric and electronic properties have been synthesized, and their activities in catalyzing intermolecular hydroamination reactions have been studied and compared. In

Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst

An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.

Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives. Copyright

A general study of [(η5-Cp′)2Ti(η 2-Me3SiC2SiMe3)]-catalyzed hydroamination of terminal alkynes: Regioselective formation of Markovnikov and anti-Markovnikov products and mechanistic explanation (Cp′=C (5)H(5), C(5)H(4)Et, C(5)Me(5))

A general study of the regioselective hydroamination of terminal alkynes in the presence of [(η5-Cp)2Ti(η2-Me 3SiC2SiMe3)] (1), [(η5-CpEt) 2Ti(η2-Me3SiC2SiMe3)] (CpEt= ethylcyclopentadienyl) (2), and [(η5-Cp*) 2Ti(η2-Me3SiC2SiMe3)] (Cp=pentamethylcyclopentadienyl) (3) is presented. While aliphatic amines give mainly the anti-Markovnikov products, anilines and aryl hydrazines yield the Markovnikov isomer as main products. Interestingly, using aliphatic amines such as n-butylamine and benzylamine the different catalysts lead to a significant change in the observed regioselectivity. Here, for the first time a highly selective switch from the Markovnikov to the anti-Markovnikov product is observed simply by changing the catalyst. Detailed theoretical calculations for the reaction of propyne with different substituted anilines and tert-butylamine in the presence of [(η5-C5H5)Ti(= NR)(NHR)] (R=4-C6H4X; X=H, F, Cl, CH3, 2,6-dimethylphenyl) reveal that the experimentally observed regioselectivity is determined by the relative stability of the corresponding π-complexes 10. While electrostatic stabilization favors the Markovnikov performance for aniline, the steric repulsive destabilization disfavors the Markovnikov performance for tert-butylamine.

Synthesis of β-lactams via cycloaddition of hydrazones with phenoxyketene

Phenoxyketene is capable of annelating the disubstituted hydrazones to afford stereoselectivity cis-monocyclic β-lactams with a 1-amino functionality. The ease of cycloaddition is governed by substitutents on the azomethine carbon as well as on the hydraz

Inhibiteurs mixtes des voies de la cyclooxygenase et des lipoxygenases: synthese et activite de derives hydrazoniques

Dual inhibitors of the cyclooxygenase and lipoxygenase pathways: synthesis and activity of hydrazone derivatives.Non-steroidal anti-inflammatory drugs (NSAIDs) act by preventing prostaglandin production.In recent years, research on non-steroid dual inhibitors of prostaglandin and leukotriene biosyntheses has been developed.These compounds should represent a new class of anti-inflammatory drugs, with a wider spectrum of activity than classical NSAIDs.The present paper reports the synthesis of hydrazone derivatives.The effect of various substitutions is studied on platelet cyclooxygenase (i.e. prostaglandin synthesis) and on leukocyte 5-lipoxygenase (i.e. leukotriene synthesis).Among the 50 tested compounds, 2 hydrazone derivatives were selected for their significant dual inhibitory potency: 2-acetylthiophene-2-thiazolylhydrazone 5g, and N-phenyl benzimidrazone 6c.Keywords - non-steroidal anti-inflammatory drugs / hydrazones / dual inhibitor / cyclooxygenase / lipoxygenase