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[ CAS No. 191732-72-6 ] {[proInfo.proName]}

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Chemical Structure| 191732-72-6
Chemical Structure| 191732-72-6
Structure of 191732-72-6 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Rathje, Oliver H. ; Perryman, Lara ; Payne, Richard J. , et al. DOI: PubMed ID:

Abstract: Mixed Lineage Kinase domain-Like pseudokinase (MLKL) is implicated in a broad range of diseases due to its role as the ultimate effector of necroptosis and has therefore emerged as an attractive drug target. Here, we describe the development of PROteolysis TArgeting Chimeras (PROTACs) as a novel approach to knock down MLKL through chem. means. A series of candidate degraders were synthesized from a high-affinity pyrazole carboxamide-based MLKL ligand leading to the identification of a PROTAC mol. that effectively degraded MLKL and completely abrogated cell death in a TSZ model of necroptosis. By leveraging the innate ability of these PROTACs to degrade MLKL in a dose-dependent manner, the quant. relationship between MLKL levels and necroptosis was interrogated. This work demonstrates the feasibility of targeting MLKL using a PROTAC approach and provides a powerful tool to further our understanding of the role of MLKL within the necroptotic pathway.

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Product Details of [ 191732-72-6 ]

CAS No. :191732-72-6 MDL No. :MFCD07772307
Formula : C13H13N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :GOTYRUGSSMKFNF-UHFFFAOYSA-N
M.W : 259.26 Pubchem ID :216326
Synonyms :
CC-5013
Chemical Name :3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Calculated chemistry of [ 191732-72-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.31
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 74.93
TPSA : 92.5 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : -0.5
Log Po/w (WLOGP) : -0.88
Log Po/w (MLOGP) : 0.14
Log Po/w (SILICOS-IT) : 0.61
Consensus Log Po/w : 0.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.3
Solubility : 13.0 mg/ml ; 0.0501 mol/l
Class : Very soluble
Log S (Ali) : -0.97
Solubility : 27.5 mg/ml ; 0.106 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.406 mg/ml ; 0.00157 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.33

Safety of [ 191732-72-6 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P501-P202-P201-P280-P308+P313-P405 UN#:N/A
Hazard Statements:H360 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 191732-72-6 ]

* 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 [ 191732-72-6 ]

[ 191732-72-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 51951-05-4 ]
  • [ 191732-72-6 ]
  • C21H27N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Weigh 2.08g compound 63 (10mmol, 1eq.), add 100mL THF to dissolve, add 3.87g DIPEA (30mmol, 3eq), stir at room temperature for 10min, add 5.70g HATU (15mmol, 1.5eq.), stir at 40C for 30min, add 3.10 g of compound 6 (12 mmol, 1.2 eq.), reacted at 40C for 5 h, cooled to room temperature after the reaction was completed, and rotary-evaporated under reduced pressure to obtain the crude product, separated by silica gel column chromatography (DCM:MeOH=3:1), dried Dried compound 11 white powder 2.56g, yield 60%;
  • 2
  • [ 51951-05-4 ]
  • [ 191732-72-6 ]
  • C47H51ClN12O10S [ No CAS ]
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[ 191732-72-6 ]

Chemical Structure| 1243329-97-6

A451300[ 1243329-97-6 ]

3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochloride

Reason: Free-salt

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