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Chemical Structure| 592-51-8 Chemical Structure| 592-51-8

Structure of 592-51-8

Chemical Structure| 592-51-8

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Product Citations

Product Citations

Andrew R. Mahoney ; Kelly M. Storek ; William M. Wuest ;

Abstract: The search for antibiotics that function through novel mechanisms of action is ongoing, and recent progress in our lab identified the tricarboxylic acid cycle as a viable option. Promysalin is a secondary metabolite capable of species-specific inhibition of Pseudomonas aeruginosa, a common opportunistic pathogen. Promysalin disrupts primary metabolism in this bacterium by competitively inhibiting succinate dehydrogenase at the ubiquinone binding site. However, the activity of promysalin in cellulo is marred potentially by its chemical instability and/or propensity for efflux. To assess the success of these novel analogues, a novel strain of P. aeruginosa harboring gene deletions of eight efflux pumps and porins was developed and implemented. Herein, we disclose the synthesis and biological investigation of six promysalin analogues to overcome these liabilities and demonstrate that efflux likely plays a significant role in tolerating the effect of the inhibitor.

Purchased from AmBeed: ; 24850-33-7 ; 58479-61-1 ; ; 67843-74-7 ; ; 37342-97-5 ; 18162-48-6 ; 34164-50-6 ; ; 1310-73-2 ; 814-68-6 ; 111-71-7 ; 693-25-4

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Product Details of [ 592-51-8 ]

CAS No. :592-51-8
Formula : C5H7N
M.W : 81.12
SMILES Code : C=CCCC#N
MDL No. :MFCD00151259
InChI Key :CFEYBLWMNFZOPB-UHFFFAOYSA-N
Pubchem ID :11604

Safety of [ 592-51-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H301-H315-H319
Precautionary Statements:P210-P233-P241-P264-P270-P280-P362-P405-P501
Class:6.1(3)
UN#:3275
Packing Group:

Application In Synthesis of [ 592-51-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 592-51-8 ]

[ 592-51-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 592-51-8 ]
  • [ 2905-65-9 ]
  • [ 1421698-88-5 ]
YieldReaction ConditionsOperation in experiment
99% NaHMDS (2M, 5.50 mL) was added to a solution of pent-4-enenitrile (0.97 mL, 10.0 mmol) in anhydrous THF (50 mL) at -78 oC. After stirring for 15 min, methyl-3-chlorobenzoate (1.88 g) was added and the reaction was stirred for 30 min befor warming to room temperature. The reaction was quenched by addition of 1N HCl solution, then extracted with EtOAc (x 2). The combined organics were dried and concentrated to give the acylated nitrile (2.18 g, 99%). Hydroxylamine hydrochloride (382 mg) was added to a solution of the acylated nitrile (1.1 g) in pyridine (10 mL) and the reaction was stirred at 80 oC for 3 hours. After cooling to room temperature, EtOAc and sat. NH4Cl solution were added and the layers separated. The organic was washed with brine, dried over Na2SO4 and concentrated to give the amino-isoxazole as a yellow oil (1.05 g, 89%) which was used directly. The residue was dissolved in pyridine (5 mL) and cooled in an ice-bath. AcCl (0.36 g, 4.5 mmol) was added and the reaction was stirred for 30 min before warming to room temperature for a further 30 min. The volatiles were removed under vacuum and the residue was purified by silica gel chromatography [heptane/EtOAc, 9:1 - 3:1] to give the product as a colourless oil (0.96 g, 77%). The N-acyl intermediate (950 mg, 3.43 mmol) was then N-alkylated with allyl bromide and NaH to give the product 19 as a colourless oil (855 mg, 79%)
 

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