MK-1775

Base Information

• Chemical Name: MK-1775
• CAS No.: 955365-80-7
• Molecular Formula: C27H32N8O2
• Molecular Weight: 500.603
• Mol file: 955365-80-7.mol

Synonyms:2-allyl-1,8-dimethoxyanthracene-9,10-dione;2-allyl-1,8-dimethoxy-9,10-anthraquinone;2-allyl-1-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one;9,10-Anthracenedione,1,8-dimethoxy-2-(2-propenyl);

Chemical Property of MK-1775

Chemical Property:

• Boiling Point: 723.804 °C at 760 mmHg
• PKA: 13.27±0.29(Predicted)
• Flash Point: 391.543 °C
• PSA: 104.34000
• Density: 1.293 g/cm³
• LogP: 2.96190
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (70 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

MK 1775 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: MK-1775 is a small molecule inhibitor of the tyrosine kinase WEE1 with potential antineoplastic sensitizing activity. MK-1775 selectively targets and inhibits WEE1, a tyrosine kinase that phosphorylates cyclin-dependent kinase 1 (CDK1, CDC2) to inactivate the CDC2/cyclin B complex. Inhibition of WEE1 activity prevents the phosphorylation of CDC2 and impairs the G2 DNA damage checkpoint. This may lead to apoptosis upon treatment with DNA damaging chemotherapeutic agents. MK-1775 is a type of biological therapy. It is a cancer growth blocker. It stops signals that cancer cells use to divide and grow. MK-1775 has been used in trials studying the treatment of LYMPHOMA, Neoplasms, Ovarian Cancer, Tongue Carcinoma, and Adult Glioblastoma, among others.
• Uses: MK 1775 is used in biological studies for the abrogation of G2/M checkpoint through WEE1 inhibition in combination with chemotherapy as a promising therapeutic approach for mesothelioma.

Technology Process of MK-1775

There total 7 articles about MK-1775 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: 79.3%

2-allyl-1-(6-(2-hydroxypropane-2-yl)pyridin-2-yl)-6-((4-(4-methylpiperazine)-1-yl)phenyl)amino-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (955369-56-9) + 4-(4-Methyl-piperazino)-anilin (16153-81-4) → MK-1775 (955365-80-7)

Guidance literature:

2-allyl-1-(6-(2-hydroxypropane-2-yl)pyridin-2-yl)-6-((4-(4-methylpiperazine)-1-yl)phenyl)amino-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one; With 3-chloro-benzenecarboperoxoic acid; In toluene; at 20 ℃; for 1h;

4-(4-Methyl-piperazino)-anilin; With N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃; for 18h;

Reference yield:

4-(4-Methyl-piperazino)-anilin (16153-81-4) → MK-1775 (955365-80-7)

Guidance literature:

2-allyl-1-(6-(2-hydroxypropane-2-yl)pyridin-2-yl)-6-((4-(4-methylpiperazine)-1-yl)phenyl)amino-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one; With 3-chloro-benzenecarboperoxoic acid; In water; toluene; for 0.333333h;

4-(4-Methyl-piperazino)-anilin; With N-ethyl-N,N-diisopropylamine; In water; toluene;

Reference yield:

methyl 6-Bromopicolinate (26218-75-7) → MK-1775 (955365-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethyl ether / 0.08 h / 20 °C / Inert atmosphere

2.1: potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide / 1,4-dioxane / 18 h / 80 - 95 °C

3.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1 h / 20 °C

3.2: 18 h / 20 °C

With copper(l) iodide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; N,N`-dimethylethylenediamine; In 1,4-dioxane; diethyl ether; toluene; 2.1: |Ullmann Condensation;

DOI:10.1002/cmdc.201800188

upstream raw materials:

4-(4-Methyl-piperazino)-anilin

2-allyl-1-(6-(2-hydroxypropane-2-yl)pyridin-2-yl)-6-((4-(4-methylpiperazine)-1-yl)phenyl)amino-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one

2-(6-bromopyridin-2- yl)propan-2-ol

methyl 6-Bromopicolinate

Refernces

• 1、 Matheson, Christopher J.,Casalvieri, Kimberly A.,Backos, Donald S.,Reigan, Philip. "Development of Potent Pyrazolopyrimidinone-Based WEE1 Inhibitors with Limited Single-Agent Cytotoxicity for Cancer Therapy". supporting information. p. 1681 - 1694. Retrieved 2018/08/01.
• 2、 -. "COMPOSITIONS AND METHODS FOR TREATING CANCER". Page/Page column 32. . Retrieved 2014/05/07.