1380432-32-5

Usage

Uses

Used in Pharmaceutical Industry:
N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine is used as an EHop inhibitor for studying signaling diversity during Chlamydia trachomatis cell entry. It plays a crucial role in understanding the molecular mechanisms involved in the infection process and may contribute to the development of novel therapeutic strategies against this bacterial pathogen.
N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine is also used as a RAC inhibitor, which can be applied in the research and development of treatments for various diseases, including cancer. By inhibiting the activity of Rac1 and Rac3, N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine can potentially interfere with the signaling pathways that promote cell migration and tumor growth, making it a valuable tool in the fight against cancer.
Additionally, N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine has been shown to increase Rho GTPase RhoA activity at concentrations greater than 2 μM, which may have implications in the study and treatment of various diseases related to RhoA signaling.

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

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

Relevant academic research and scientific papers

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.

Novel Small-Molecule Inhibitors of Rac1 in Metastatic Breast Cancer

A novel inhibitor of Rac activity based on the structure of the established Rac/Rac-GEF inhibitor NSC23766 is discloses. The compound EHop-016, with an IC50 of 1.1 μM, is a 100-fold more efficient inhibitor of Rac activity than NSC23766. EHop-016 is specific for Rac1 and Rac3 at concentrations ≦5 mM. At higher concentrations, EHop-016 inhibits the close homolog Cdc42. In MDA-MB-435 cells, EHop-016 (≦5 mM) inhibits the association of the Rac-GEF Vav2 with a nucleotide-free Rac1(G15A), which has a high affinity for activated GEFs. EHop-016 does not affect the association of the Rac-GEF Tiam-1 with Rac1(G15A) at similar concentrations. EHop-016 also inhibits the Rac activity of MDA-MB-231 metastatic breast cancer cells and reduces Rac-directed lamellipodia formation in both cell lines. EHop-016 decreases Rac-downstream effects of p21-activated kinase (PAK)1 activity and directed migration of metastatic cancer cells. At low concentrations (5 μM), EHop-016 does not affect cell viability.