RKI1447

Base Information

• Chemical Name: RKI1447
• CAS No.: 1342278-01-6
• Molecular Formula: C16H14N4O2S
• Molecular Weight: 326.379
• Mol file: 1342278-01-6.mol

Synonyms:RKI 1447;RKI1447;RKI-1447;Urea, N-[(3-hydroxyphenyl)methyl]-N'-[4-(4-pyridinyl)-2-thiazolyl]-;1-(3-Hydroxybenzyl)-3-[4-(pyridin-4-yl)thiazol-2-yl]urea RKI 1447;RKI 1447 1-(3-Hydroxybenzyl)-3-[4-(pyridin-4-yl)thiazol-2-yl]urea;RKI-1447, >=98%

Chemical Property of RKI1447

Chemical Property:

• PKA: 6.36±0.70(Predicted)
• PSA: 118.87000
• Density: 1.408±0.06 g/cm3(Predicted)
• LogP: 3.50980
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

98% min ^*data from raw suppliers

RKI-1447 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: RKI-1447 is an inhibitor of the Rho-associated kinases ROCK1 and 2 (IC50s = 14.5 and 6.2 nM, respectively) that functions by binding to the ATP binding site of the kinase. In cancer cells, RKI-1447 at a concentration of 100 nM has been found to suppress the activation of ROCK substrates myosin light chain (MLC)-2 and the MLC phosphatase PP1 regulatory subunit MYPT1 without effect on the phosphorylation of Akt, MEK, or S6 kinase. Furthermore, it can prevent ROCK-mediated migration, invasion, and anchorage-independent growth of MDA-MB-231 breast cancer cells (IC50 = 709 nM).
• Uses: RKI-1447 is a potent and selective ROCK1 and ROCK2 inhibitor with significant anti-invasive and anti-tumor activies.

Technology Process of RKI1447

There total 5 articles about RKI1447 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: 59.0%

1-(3-methoxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea (1342276-76-9) + 3-hydroxybenzylamine (73604-31-6) → 1-(3-hydroxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea (1342278-01-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Autoclave;

DOI:10.1039/c2md00320a

Reference yield: 59.0%

→ 1-(3-hydroxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea (1342278-01-6)

Guidance literature:

Reference yield:

4-bromoacetylpyridine hydrobromide (5349-17-7) → 1-(3-hydroxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea (1342278-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1: ethanol / 0.5 h / 100 °C / Microwave irradiation

2: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: tetrahydrofuran; acetonitrile / 0.33 h / 100 °C / 11377.6 Torr / Microwave irradiation; Autoclave

4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Autoclave

With pyridine; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1039/c2md00320a

upstream raw materials:

4-bromoacetylpyridine hydrobromide

phenyl 4-(pyridin-4-yl)thiazol-2-ylcarbamate

1-(3-methoxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea

3-hydroxybenzylamine

Downstream raw materials:

1-(3-hydroxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea methanesulfonate

1-(3-hydroxybenzyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea hydrochloride

Refernces

• 1、 -. "PYRIDYLTHIAZOLE-BASED UREAS AS INHIBITORS OF RHO ASSOCIATED PROTEIN KINASE (ROCK) AND METHODS OF USE". Page/Page column 73. . Retrieved 2011/11/01.