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Chemical Structure| 564483-18-7 Chemical Structure| 564483-18-7
Chemical Structure| 564483-18-7

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CAS No.: 564483-18-7

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Synonyms: 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl

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Wilms, Gerrit ; Schofield, Kevin ; Maddern, Shayna ; Foley, Christopher ; Shaw, Yeng ; Smith, Breland , et al.

Abstract: Small-molecule-induced protein degradation has emerged as a promising pharmacological modality for inactivating disease-relevant protein kinases. DYRK1A and DYRK1B are closely related protein kinases that are involved in pathological processes such as neurodegeneration, cancer development, and adaptive immune homeostasis. Herein, we report the development of the first DYRK1 proteolysis targeting chimeras (PROTACs) that combine a new ATP-competitive DYRK1 inhibitor with ligands for the component cereblon (CRBN) to induce ubiquitination and subsequent proteasomal degradation of DYRK1A and DYRK1B. The lead compound (DYR684) promoted fast, efficient, potent, and selective degradation of DYRK1A in cell-based assays. Interestingly, an enzymatically inactive splicing variant of DYRK1B (p65) resisted degradation. Compared to competitive kinase inhibition, targeted degradation of DYRK1 by DYR684 provided improved suppression of downstream signaling. Collectively, our results identify DYRKs as viable targets for PROTAC-mediated degradation and qualify DYR684 as a useful chemical probe for DYRK1A and DYRK1B.

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Duszczak-Kaczmarek, Julia ; Mitu?a-Chmielowiec, Katarzyna ; Rzonsowska, Monika ; Jankowski, Wojciech ; Hoffmann, Marcin ; Walkowiak, J?drzej , et al.

Abstract: We present a methodology for the synthesis of inorganic-organic Janus-type molecules based on mono-T8 and difunctionalized double-decker (DDSQs) via hydrosilylation reactions, achieving exceptionally high yields and selectivities. The synthesized compounds were extensively characterized using various spectroscopic techniques, and their sizes and spatial arrangements were predicted through molecular modelling and density functional theory (DFT) calculations. Quantum chemical calculations were employed to examine the interactions among four molecules of the synthesized compounds. These computational results allowed us to determine the propensity for molecular aggregation, identify the functional groups involved in these interactions, and understand the changes in interatomic distances during aggregation. Understanding the aggregation behaviour of silsesquioxane molecules is crucial for tailoring their properties for specifc applications, such as nanocomposites, surface coatings, drug delivery systems, and catalysts. Through a combination of experimental and computational approaches, this study provides valuable insights into the design and optimization of silsesquioxane-based Janus-type molecules for enhanced performance across various felds.

Keywords: Silsesquioxane ; DDSQ ; Janus compounds ; Catalysis ; Hydrosilylation ; Molecular modeling ; DFT

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Alternative Products

Product Details of Xphos

CAS No. :564483-18-7
Formula : C33H49P
M.W : 476.72
SMILES Code : C1(CCCCC1)P(C2=C(C=CC=C2)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C)C4CCCCC4
Synonyms :
2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl
MDL No. :MFCD04117682
InChI Key :UGOMMVLRQDMAQQ-UHFFFAOYSA-N
Pubchem ID :11155794

Safety of Xphos

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of Xphos

* 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 [ 564483-18-7 ]

[ 564483-18-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 120-72-9 ]
  • potassium phosphate [ No CAS ]
  • [ 890315-75-0 ]
  • [ 131274-22-1 ]
  • [ 564483-18-7 ]
  • [ 890313-93-6 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); In ethyl acetate; toluene; Example 407 33 mg of 1H-indole, 0.12 g of cesium carbonate, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 33 mg of 1H-indole, 79 mg of tripotassium phosphate, 5.1 mg of tris (dibenzylideneacetone) dipalladium (0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10percent citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 20:1] to obtain 45 mg of tert-butyl 2-(benzamido)-4-(1H-indol-1-yl)benzoate as colorless oil. 1H-NMR (CDCl3) delta: 1. 67 (9H, s), 6.73 (1H, d, J = 3.4 Hz), 7.18-7.22 (1H, m), 7.25-7.33 (2H, m), 7.48 (1H, d, J = 3.4 Hz), 7.51-7.62 (3H, m), 7.66-7.70 (1H, m), 7.83 (1H, d, J = 8.3 Hz), 8.06-8.10 (2H, m), 8.17 (1H, d, J = 8.8 Hz), 9.22 (1H, d, J = 2.2 Hz), 12.35 (1H, s).
  • 2
  • [ 109-97-7 ]
  • [ 890315-75-0 ]
  • [ 131274-22-1 ]
  • [ 564483-18-7 ]
  • [ 890313-92-5 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); In ethyl acetate; toluene; Example 406 0.019 mL of 1H-pyrrole, 0.12 g of cesium carbonate, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10percent citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 60 mg of tert-butyl 2-(benzamido)-4-(1H-pyrrol-1-yl)benzoate as white solid. 1H-NMR (CDCl3) delta: 1.65 (9H, s), 6.38 (2H, t, J = 2.2 Hz), 7.12 (1H, dd, J = 8.6, 2.3 Hz), 7.25-7.28 (2H, m), 7.51-7.61 (3H, m), 8.05-8.10 (3H, m), 9.16 (1H, d, J = 2.3 Hz), 12.36 (1H, s).
  • 3
  • [ 13078-80-3 ]
  • [ 14267-08-4 ]
  • [ 917-54-4 ]
  • [ 564483-18-7 ]
  • [ 1028206-56-5 ]
  • 4
  • (N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II) [ No CAS ]
  • [ 13078-80-3 ]
  • [ 564483-18-7 ]
  • [ 1028206-56-5 ]
  • 5
  • di(2-(2′-amino-1,1′-biphenyl))palladium(II) methanesulfonate dimer [ No CAS ]
  • [ 564483-18-7 ]
  • [ 1445085-55-1 ]
YieldReaction ConditionsOperation in experiment
92% In tetrahydrofuran; at 20.0℃; for 0.75h;Inert atmosphere; A 300-mL round-bottomed flask equipped with a stir bar and rubber septum was charged with mu-OMs dimer 3 (11.92 g, 15.25 mmol, 0.50 eq) and XPhos (14.52 g, 30.5 mmol, 1.00 eq). The flask was evacuated under vacuum and backfilled with argon (this procedure was repeated twice), after which THF (120 mL) was added. The reaction mixture was stirred at room temperature for 45 min. After removal of 90% of the solvent under vacuum the product was precipitated from pentane to afford the title compound as an off-white solid as the 1:1 THF complex. THF could be removed by dissolving the solid in DCM and reprecipitating with pentane. Yield: 25.5 g, 92%. FIG. 7. [0295] FIG. 8 tabulates the % yield of various precatalysts formed using the procedures outlined above.
  • 6
  • [ 123-91-1 ]
  • [ 72287-26-4 ]
  • [ 15864-32-1 ]
  • [ 24424-99-5 ]
  • [ 96042-30-7 ]
  • [ 564483-18-7 ]
  • [ 1244059-50-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; potassium acetate; Step 1: tert-Butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate A 100 mL flask charged with 2-amino-6-bromobenzothiazole (2.52 g, 10.77 mmol), bis(pinacolato)diboron (5.45 g, 21.24 mmol), potassium acetate (3.28 g, 33.09 mmol), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (212.2 mg, 0.436 mmol), and tris(dibenylideneacetone)dipalladium chloroform complex (117.9 mg, 0.110 mmol) was evacuated and backfilled with nitrogen. 1,4-Dioxane (20.0 mL, 233 mmol) was added and the reaction mixture stirred under a nitrogen balloon at 100° C. for 1 h. To the reaction was then added [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (285.9 mg, 0.350 mmol). After an additional 17 h the reaction mixture was cooled to room temperature, filtered through celite, rinsing with ethyl acetate, and then evaporated to dry on celite. The crude product was purified via flash chromatography on silica gel (80 g silica, solvent gradient: 0-100percent isopropyl acetate in heptanes) to yield 2.85 g. Of this material, 2.64 g was combined with di-tert-butyl dicarbonate (2.58 g, 11.45 mmol), 4-dimethylaminopyridine (79.9 mg, 0.654 mmol) and DCM (20.0 mL, 312 mmol) and stirred at room temperature for 2 h. The mixture was evaporated in vacuo and the crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-50percent ethyl acetate in heptane) to yield 2.24 g of the title compound. LCMS (ESI): [M+H]+=377.
 

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