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Chemical Structure| 38767-72-5 Chemical Structure| 38767-72-5
Chemical Structure| 38767-72-5

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Product Citations

Product Citations

Ingraham, Charles H. IV ; Stalinska, Joanna ; Carson, Sean C. ; Colley, Susan B. ; Rak, Monika ; Lassak, Adam , et al.

Abstract: Glioblastomas are highly aggressive brain tumors for which therapeutic options are very limited. In a quest for new anti-glioblastoma drugs, we focused on specific structural modifications to the benzoyl-phenoxy-acetamide (BPA) structure present in a common lipid-lowering drug, fenofibrate, and in our first prototype glioblastoma drug, PP1. Here, we propose extensive computational analyses to improve the selection of the most effective glioblastoma drug candidates. Initially, over 100 structural BPA variations were analyzed and their physicochemical properties, such as water solubility (- logS), calculated partition coefficient (ClogP), probability for BBB crossing (BBB_SCORE), probability for CNS penetration (CNS-MPO) and calculated cardiotoxicity (hERG), were evaluated. This integrated approach allowed us to select pyridine variants of BPA that show improved BBB penetration, water solubility, and low cardiotoxicity. Herein the top 24 compounds were synthesized and analyzed in cell culture. Six of them demonstrated glioblastoma toxicity with IC50 ranging from 0.59 to 3.24 µM. Importantly, one of the compounds, HR68, accumulated in the brain tumor tissue at 3.7 ± 0.5 µM, which exceeds its glioblastoma IC50 (1.17 µM) by over threefold.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; 2706-56-1 ; ; ; ; ; ; ; ; 20173-24-4 ; ; ; ; ; ; ; ; 42017-89-0 ; 90-45-9

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Product Details of 4-Amino-1H-pyridin-2-one

CAS No. :38767-72-5
Formula : C5H6N2O
M.W : 110.11
SMILES Code : O=C1C=C(N)C=CN1
MDL No. :MFCD09832889
InChI Key :SBQVQYPJWLJRQT-UHFFFAOYSA-N
Pubchem ID :573530

Safety of 4-Amino-1H-pyridin-2-one

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Amino-1H-pyridin-2-one

* 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.

  • Upstream synthesis route of [ 38767-72-5 ]

[ 38767-72-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 38767-72-5 ]
  • [ 96530-75-5 ]
YieldReaction ConditionsOperation in experiment
60% at -20 - 60℃; for 3.5 h; To a cooled solution of HF-pyridine complex (70percent, 13.1 mL) at 0°C was slowlyadded 4-amino-2-pyridone 5 (1.85 g, 16.8 mmol). The mixture was cooled to -20°Cand tBuONO (3.0 mL, 25.2 mmol) was slowly added. The reaction mixture wasstirred at -20°C for 0.5h, then allowed to warm to r.t. for 2h and finally heated at 60°Cfor 1h. The mixture was cooled to 0°C and sat. aq. Na2CO3 was added. The aqueouslayer was extracted with ethyl acetate (5x), and the combined organic layers weredried (Na2SO4), filtered and concentrated under reduced pressure. The crude waspurified by flash chromatography on silica gel (DCM/MeOH: 95/5) to give 1a (1.14 g,60percent) as a colorless solid.
References: [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69.
 

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