KU-0063794

Base Information

• Chemical Name: KU-0063794
• CAS No.: 938440-64-3
• Molecular Formula: C₂₅H₃₁N₅O₄
• Molecular Weight: 465.552
• Mol file: 938440-64-3.mol

Synonyms:KU 0063794

Chemical Property of KU-0063794

Chemical Property:

• Vapor Pressure: 3.09E-20mmHg at 25°C
• Refractive Index: 1.609
• Boiling Point: 694.3 °C at 760 mmHg
• PKA: 14.20±0.10(Predicted)
• Flash Point: 373.7 °C
• PSA: 93.07000
• Density: 1.248 g/cm³
• LogP: 2.77290
• Storage Temp.: Store at RT
• Solubility.: DMSO: >2mg/mL (warmed)

Purity/Quality:

99.0% ^*data from raw suppliers

Ku 0063794 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Description: The mammalian target of rapamycin (mTOR) is a serine-threonine kinase which acts as part of two distinct complexes, TORC1 and TORC2. Both complexes (TORC1/2) play central roles in cell growth, gene expression, angiogenesis, and cell survival. Ku-0063794 is a cell-permeable, selective dual inhibitor of mTORC1 and mTORC2 (IC50 = 10 nM). It does not affect the activity of 76 other protein kinases or seven lipid kinases, including PI3Ks. Ku-0063794 inhibits cell growth by inducing G1-cell cycle arrest and autophagy, but not apoptosis, and inhibits tumor growth in a xenograft model of renal cell carcinoma (8 mg/kg for 46 days).
• Uses: Ku 0063794 is a specific mammalian target of rapamycin (mTOR) inhibitor and may be used for the treatment of cancers. KU 0063794 has been used: as a mammalian target of rapamycin (mTOR) inhibitor to study the effects of follicular stimulating hormone (FSH) in mTOR phosphorylation and vascular cell adhesion molecule-1 (VCAM-1) expression in?human umbilical vascular endothelial cells (HUVECs) as a mTOR inhibitor to treat effector memory (EM) CD8+ T cells for metabolic flux analysis as an autophagy inducer to demonstrate the utility of p62 and LC3B-II quantification in HEK293T cells and primary cultures of rat neurons and astrocytes using time-resolved fluorescence resonance energy transfer (TR-FRET)

Technology Process of KU-0063794

There total 9 articles about KU-0063794 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: 75.0%

7-chloro-2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-4-morpholin-4-yl-pyrido[2,3-d]pyrimidine (938443-23-3) + [2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1009303-77-8) → KU-63794 (938440-64-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; at 140 ℃;

DOI:10.1016/j.bmcl.2013.01.019

Reference yield:

2-amino-6-chloro-pyridine-3-carboxamide (64321-24-0) → KU-63794 (938440-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / 115 °C

2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 100 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 70 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / 140 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In ethanol; dichloromethane; N,N-dimethyl acetamide; toluene;

DOI:10.1016/j.bmcl.2013.01.019

Reference yield:

2,6-dichloropyridine-3-carboxylic acid (38496-18-3) → KU-63794 (938440-64-3)

Guidance literature:

Multi-step reaction with 8 steps

1: ammonia / 130 °C / 13501.4 Torr

2: thionyl chloride / tetrahydrofuran / 20 °C

3: ammonia / tetrahydrofuran / 20 °C

4: toluene / 115 °C

5: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 100 °C

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 70 °C

8: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / 140 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; ammonia; sodium carbonate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; toluene;

DOI:10.1016/j.bmcl.2013.01.019

upstream raw materials:

7-chloro-2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-4-morpholin-4-yl-pyrido[2,3-d]pyrimidine

(3-(hydroxymethyl)-4-methoxy)phenylboronic acid

2,6-dichloropyridine-3-carboxylic acid

2-amino-6-chloro-pyridine-3-carboxamide

Refernces

• 1、 -. "PYRIDO-,PYRAZO- AND PYRIMIDO-PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS". Page/Page column 61-62. . Retrieved 2008/06/13.