345-53-9

Basic information

• Product Name: 2-(4-fluorophenyl)-3-oxopentanenitrile
• Synonyms: 2-(4-fluorophenyl)-3-oxopentanenitrile
• CAS NO: 345-53-9
• Molecular Weight: 191.205
• Mol File: 345-53-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-fluorophenyl)-3-oxopentanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-fluorophenyl)-3-oxopentanenitrile(345-53-9)
• EPA Substance Registry System: 2-(4-fluorophenyl)-3-oxopentanenitrile(345-53-9)

Safety Data

• Hazardous Substances Data: 345-53-9(Hazardous Substances Data)

Upstream product

• 33279-01-5 3-oxo-pentanenitrile 
• 352-34-1 4-fluoro-1-iodobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 554-12-1 propanoic acid methyl ester 
• 459-22-3 4-fluorophenylacetonitrile 
• 105-37-3 Ethyl propionate 

Downstream Products

• 314-75-0 6-ethyl-5-(4-fluoro-phenyl)-pyrimidine-2,4-diyldiamine 
• 1031699-69-0 3-ethyl-4-(4-fluorophenyl)-1H-pyrazol-5-amine 

Relevant articles and documents

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

Ametoctradin is a Potent Qo Site Inhibitor of the Mitochondrial Respiration Complex III

Ametoctradin is a new Oomycete-specific fungicide under development by BASF. It is a potent inhibitor of the bc1 complex in mitochondrial respiration. However, its detailed action mechanism remains unknown. In the present work, the binding mode of ametoctradin was first uncovered by integrating molecular docking, MD simulations, and MM/PBSA calculations, which showed that ametoctradin should be a Qo site inhibitor of bc1 complex. Subsequently, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized to further understand the substituent effects on the 5- and 6-position of 1,2,4-triazolo[1,5-a]pyrimidine. The calculated binding free energies (ΔGcal) of newly synthesized analogues as Qo site inhibitors correlated very well (R2 = 0.96) with their experimental binding free energies (ΔGexp). Two compounds (4a and 4c) with higher inhibitory activity against porcine SQR than ametoctradin were successfully identified. The structural and mechanistic insights obtained from the present study will provide a valuable clue for future designing of a new promising bc1 inhibitor.