ChemicalBook > CAS DataBase List > 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-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine

Product Name
N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine
CAS No.
1380432-32-5
Chemical Name
N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine
Synonyms
EHop-016;EHop-016, >=98%;EHOP 016;EHOP016;Rac Inhibitor III;EHop-016, 10 mM in DMSO;EHop-016, Rac GTPase inhibitor;EHOP016; EHOP-016; EHOP 016; EHOP016; EHOP-016; EHOP 016.;N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-morpholinopropyl)pyrimidine-2,4-diamine;4-N-(9-ethylcarbazol-3-yl)-2-N-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine;N4-(9-Ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-2,4-pyrimidinediamine
CBNumber
CB82631369
Molecular Formula
C25H30N6O
Formula Weight
430.55
MOL File
1380432-32-5.mol
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N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine Property

Boiling point:
633.9±65.0 °C(Predicted)
Density 
1.27
storage temp. 
2-8°C
solubility 
DMSO: soluble10mg/mL, clear
pka
7.30±0.10(Predicted)
form 
powder
color 
white to beige
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0526
Product name
EHop-016
Purity
≥98% (HPLC)
Packaging
5mg
Price
$113
Updated
2025/07/31
Sigma-Aldrich
Product number
SML0526
Product name
EHop-016
Purity
≥98% (HPLC)
Packaging
25mg
Price
$453
Updated
2025/07/31
Cayman Chemical
Product number
21557
Product name
EHop-016
Purity
≥98%
Packaging
5mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
21557
Product name
EHop-016
Purity
≥98%
Packaging
10mg
Price
$87
Updated
2024/03/01
Cayman Chemical
Product number
21557
Product name
EHop-016
Purity
≥98%
Packaging
25mg
Price
$190
Updated
2024/03/01
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N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine Chemical Properties,Usage,Production

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.

Synthesis

123-00-2

1380432-31-4

1380432-32-5

Synthesis of EHop-016 1H and 13C NMR spectra were recorded on a Bruker 400MHz spectrometer. Mass spectra were obtained on a Hewlett Packard 6890N GC/MS spectrometer. All chemicals were purchased from Sigma Aldrich Chemical Company.The synthesis of EHop-016 (5) was carried out in two steps according to the reaction scheme provided in Figure 1. A process similar to the one described in the literature was carried out as shown in Figure 1(A). (2-Chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine 3 was obtained as a pure compound in 53% yield. The product was identified by TLC, NMR and GC/MS. rf = 0.23 (3:1, hexane-ethyl acetate); 1H NMR (DMSO-d6, 400MHz) δ 1.32 (t, J = 6.9Hz, 3H), 4.45 (q, J = 6.6Hz, 2H), 6.72 (s, 1H), 7.20 (t, J = 7.36Hz, 1H ), 7.47 (t, J = 7.30 Hz, 1H), 7.56 (s, 1H), 7.62 (t, J = 8.68 Hz, 1H), 8.11 (t, J = 7.36 Hz, 1H), 8.27 (s, 1H), 10.1 (s, 1H); 13C NMR (DMSO-d6, 100MHz) δ 13.7, 37.0, 109.2, 109.4, 115.0, 118.7, 120.3, 121.3, 121.9, 122.3, 125.9, 129.9, 136.9, 140.0, 156.9, 159.6, 162.4; LRGC-MS m/z (relative percent): [M]+ 276 (100), [M-Cl]+ 241 (40), [M-C5H5N3Cl]+ 134 (26). N4-(9-ethyl-9H-carbazol-3-yl)-N2-(3-morpholin-4-yl-propyl)-pyrimidine-2,4-diamine 5 (EHop-016) was obtained as a pure compound in 93% yield. The product was identified as essentially pure by TLC and NMR: Rf = 0.34 (9:1, CH2Cl2-MeOH); 1H NMR (DMSO-d6, 400 MHz) δ 1.31 (t, J = 7.0 Hz, 3H), 1.73 (m, 2H), 2.32 (m, 2H), 2.34 (t, J = 6.89 Hz, 8H), 3.52 (m, 2H), 4.42 (q, J = 7.0 Hz, 2H), 5.98 (d, J = 5.7 Hz, 1H), 6.69 (t, J = 5.3 Hz, 1H), 7.16 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.2 Hz, 1H), 7.53 (t, J = 9.0 Hz, 4H), 7.81 ( d, J = 5.4 Hz, 1H), 8.10 (s, 1H), 8.66 (s, 1H), 9.1 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 13.7, 26.2, 36.9, 53.4, 56.3, 66.2, 108.9, 109.0, 118.2, 119.7, 120.2, 122.0, 122.2, 125.6, 132.5, 135.5, 139.9, 159.8, 160.9, 162.1.

target

Rac1

storage

Store at -20°C

References

[1] Patent: US2013/172552, 2013, A1. Location in patent: Paragraph 0031

N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine manufacturers

Career Henan Chemical Co
Product
4-N-(9-ethylcarbazol-3-yl)-2-N-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine 1380432-32-5
Price
US $1.00/KG
Min. Order
1KG
Purity
Min98% HPLC
Supply Ability
g/kg/ton
Release date
2019-12-23

1380432-32-5, N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMineRelated Search:

Mdivi-1 2-(4-broMo-2-chlorophenoxy)-N-(4-(N-(4,6-diMethylpyriMidin-2-yl)sulfaMoyl)phenylcarbaMothioyl)acetaMide Y27632 (hydrochloride) NSC 23766 (hydrochloride) EHT1864 Rapamycin

  • EHop-016
  • 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-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%
  • EHOP016; EHOP-016; EHOP 016; EHOP016; EHOP-016; EHOP 016.
  • EHOP 016;EHOP016
  • 4-N-(9-ethylcarbazol-3-yl)-2-N-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine
  • 2,4-Pyrimidinediamine, N4-(9-ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-
  • N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-Morpholin-4-yl-propyl)-pyriMidine-2,4-diaMine USP/EP/BP
  • N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-morpholinopropyl)pyrimidine-2,4-diamine
  • EHop-016, Rac GTPase inhibitor
  • EHop-016, 10 mM in DMSO
  • Rac Inhibitor III
  • 1380432-32-5
  • Inhibitors