N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine

Base Information

• Chemical Name: N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine
• CAS No.: 1380432-32-5
• Molecular Formula: C₂₅H₃₀N₆O
• Molecular Weight: 430.553
• Mol file: 1380432-32-5.mol

Synonyms:EHop-016;N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine;N4-(9-Ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-2,4-pyrimidinediamine;N4-(9-Ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-2,4-pyrimidinediamine Ehop-016;EHop-016, >=98%

Chemical Property of N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine

Chemical Property:

• Boiling Point: 633.9±65.0 °C(Predicted)
• PKA: 7.30±0.10(Predicted)
• PSA: 73.70000
• Density: 1.27
• LogP: 3.26390
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear

Purity/Quality:

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

EHop-016 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: EHop-016 is an inhibitor of the small Rho GTPases Rac1 and Rac3. It inhibits Rac1 activity in MDA-MB-435 breast cancer cells with an IC50 value of 1.1 μM in a Rac1 activation assay. At a concentration of 1 μM, EHop-016 inhibits 58% of Rac3 activity, and it inhibits Cdc42 activity but only at higher concentrations (5-10 μM). It also increases Rho GTPase RhoA activity ~1.3-fold at concentrations greater than 2 μM. EHop-016 (2-4 μM) inhibits Rac-regulated functions in MDA-MB-435 cells, including lamellipodia formation and serine/threonine p21-activated kinase 1 (PAK1)-mediated cell migration. In a nude mouse model of breast cancer metastasis, EHop-016 (25 mg/kg) significantly lowers mammary fat pad tumor growth, metastasis, and angiogenesis. It also inhibits mutant receptor tyrosine kinase (KIT)-induced growth in systemic mastocytosis and acute myeloid leukemia (AML) cells (≥2.5 μM).
• Uses: EHop-016 has been used as the EHop inhibitor to study signalling diversity during Chlamydia trachomatis cell entry. It has also been used as a RAC inhibitor.

Technology Process of N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine

There total 2 articles about N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine 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: 93.0%

4-(3-Aminopropyl)morpholine (123-00-2) + (2-chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine (1380432-31-4) → EHop-016 (1380432-32-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In iso-butanol; at 120 ℃; for 0.5h; Microwave irradiation;

Reference yield:

9-ethyl-9H-carbazol-3-ylamine (132-32-1) → EHop-016 (1380432-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 10 h / Reflux

2: caesium carbonate / 1,4-dioxane / 120 - 160 °C

With caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; isopropyl alcohol;

upstream raw materials:

4-(3-Aminopropyl)morpholine

(2-chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine

9-ethyl-9H-carbazol-3-ylamine

Refernces

• 1、 -. "Novel Small-Molecule Inhibitors of Rac1 in Metastatic Breast Cancer". Paragraph 0031. . Retrieved 2013/07/19.