1380432-32-5

Basic information

• Product Name: N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine
• 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%
• CAS NO: 1380432-32-5
• Molecular Formula: C25H30N6O
• Molecular Weight: 430.5453
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 1380432-32-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 633.9±65.0 °C(Predicted)
• Appearance: white to beige/
• Density: 1.27
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble10mg/mL, clear
• PKA: 7.30±0.10(Predicted)
• CAS DataBase Reference: N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine(CAS DataBase Reference)
• NIST Chemistry Reference: N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine(1380432-32-5)
• EPA Substance Registry System: N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine(1380432-32-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1380432-32-5(Hazardous Substances Data)

Usage

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.

Biochem/physiol Actions

EHop-016 is a potent and specific inhibitor of Rac1 and Rac3 GTPase activity that inhibits Vav2 interaction with Rac, Rac-activated PAK1, lamellipodia formation, and cell migration. EHop-016 inhibits the Rac activity of MDA-MB-231 metastatic breast cancer cells and reduces Rac-directed lamellipodia formation.

Upstream product

• 132-32-1 9-ethyl-9H-carbazol-3-ylamine 
• 123-00-2 4-(3-Aminopropyl)morpholine 
• 1380432-31-4 (2-chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine 

Relevant articles and documents

NOVEL CARBAZOLE EHOP-016 DERIVATIVES AS ANTI-CANCER AND ANTI-MIGRATORY AGENTS

A series of novel of EHop-016 derivatives is presented herein via designing and synthesizing compounds that mimics its more favorable “U-shaped” conformation that appears to be critical for inhibitory activity against Rac. Based on modeling studies on EHop-016, compounds with a more rigid structural conformation can mimic this “U-shaped” conformation would improve the anti-migration activity against metastatic cells. Compounds are disclosed that inhibit RhoGTPases that are useful for inhibiting hyperprofilerative and neoplastic diseases. Specifically, the compounds inhibit the GTPases Rac and Cdc42 that are overactive or overexpressed in signaling pathways in cancer and metastasis. Methods for treatment of cancer and hyperproliferative diseases are disclosed.