2-Morpholino-6-(thianthren-1-yl)-4H-pyran-4-one

Base Information

• Chemical Name: 2-Morpholino-6-(thianthren-1-yl)-4H-pyran-4-one
• CAS No.: 587871-26-9
• Molecular Formula: C₂₁H₁₇NO₃S₂
• Molecular Weight: 395.503
• UNII: O549494L5D
• ChEMBL ID: CHEMBL222102
• DSSTox Substance ID: DTXSID40207516
• NCI Thesaurus Code: C201666
• Nikkaji Number: J2.176.403E
• Pharos Ligand ID: WU5YA37C5FL2
• Wikidata: Q27074594
• Mol file: 587871-26-9.mol

Synonyms:2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one;KU 55933;KU-55933;KU55933

Chemical Property of 2-Morpholino-6-(thianthren-1-yl)-4H-pyran-4-one

Chemical Property:

• Vapor Pressure: 1.1E-15mmHg at 25°C
• Refractive Index: 1.714
• Boiling Point: 628 °C at 760 mmHg
• PKA: 0.33±0.20(Predicted)
• Flash Point: 333.6 °C
• PSA: 93.28000
• Density: 1.419 g/cm³
• LogP: 4.82420
• Storage Temp.: Desiccate at -20°C
• Solubility.: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 20 mg/ml)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 395.06498575
• Heavy Atom Count: 27
• Complexity: 643

Purity/Quality:

98%,99%, ^*data from raw suppliers

KU55933 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=CC(=O)C=C(O2)C3=C4C(=CC=C3)SC5=CC=CC=C5S4
• Description: Potent and selective ATM kinase inhibitor IC50s= 13, 2500, 9300, 16600, >100000 and >100000 nM for ATM, DNA-PK, mTOR, PI 3-kinase, PI 4-K and ATR respectively.1Decreases viability of MCF-7, A549 and HCT116 cells and decreases p21CIP1?levels?in vitro.2?Disruption of ATM signaling in primary A-T fibroblasts leads to dysregulation of ribonucleotide reductase and increase resistance to inhibitors of mitochondrial respiration and translation.3?Sensitizes radio-resistant cancer cells.4Provides neuroprotection against H2O2-induced cell damage.5
• Uses: A potent and specific ATM kinase inhibitor with an IC50 and a Ki of 13 nM and 2.2 nM, respectively. KU-55933 has been used as an ataxia-telangiectasia mutated (Atm) inhibitor.

Technology Process of 2-Morpholino-6-(thianthren-1-yl)-4H-pyran-4-one

There total 3 articles about 2-Morpholino-6-(thianthren-1-yl)-4H-pyran-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

thianthren-1-yl boronic acid (108847-76-3) + 6-chloro-2-(4-morpholin-4-yl)pyran-4-one (119671-47-5) → 2-(4-morpholinyl)-6-(1-thianthrenyl)-4H-pyran-4-one (587871-26-9)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 72h; Heating;

DOI:10.1021/jm061121y

Reference yield:

4,4-dichloro-1-(morpholin-4-yl)but-3-ene-1,2-dione (85839-49-2) → 2-(4-morpholinyl)-6-(1-thianthrenyl)-4H-pyran-4-one (587871-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / perchloric acid / dioxane / 1 h / 90 °C

2: 61 percent / K₂CO₃ / Pd(PPh₃)4 / dioxane / 72 h / Heating

With perchloric acid; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; 2: Suzuki-Miyaura coupling;

DOI:10.1021/jm061121y

Reference yield:

4-chloro-4-(2,2,2-trichloroethyl)-oxetan-2-one (81189-95-9) → 2-(4-morpholinyl)-6-(1-thianthrenyl)-4H-pyran-4-one (587871-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaHCO₃ / CH₂Cl₂ / 2.33 h / 15 °C

2: 75 percent / perchloric acid / dioxane / 1 h / 90 °C

3: 61 percent / K₂CO₃ / Pd(PPh₃)4 / dioxane / 72 h / Heating

With perchloric acid; sodium hydrogencarbonate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; 3: Suzuki-Miyaura coupling;

DOI:10.1021/jm061121y

upstream raw materials:

thianthren-1-yl boronic acid

6-chloro-2-(4-morpholin-4-yl)pyran-4-one

4,4-dichloro-1-(morpholin-4-yl)but-3-ene-1,2-dione

4-chloro-4-(2,2,2-trichloroethyl)-oxetan-2-one

Refernces

• 1、 -. "ATM inhibitors". Page/Page column 20. . Retrieved 2008/06/13.