ESI 09
- Product Name
- ESI 09
- CAS No.
- 263707-16-0
- Chemical Name
- ESI 09
- Synonyms
- ESI09;ESI 09;ESI-09;ESI-09, 10 mM in DMSO;Virus Protease,inhibit,ESI 09,ESI09,Inhibitor,ESI-09;2-(5-(tert-Butyl)isoxazol-3-yl)-N-(3-chlorophenyl)-2-oxoacetohydrazonoyl cyanide;(E)-2-(5-(tert-butyl)isoxazol-3-yl)-N-(3-chlorophenyl)-2-oxoacetohydrazonoyl cyanide;(E)-3-(5-tert-butylisoxazol-3-yl)-2-(2-(3-chlorophenyl)hydrazono)-3-oxopropanenitrile;alpha-[(3-Chlorophenyl)hydrazono]-5-(1,1-dimethylethyl)-beta-oxo-3-isoxazolepropanenitrile;α-[2-(3-Chlorophenyl)hydrazinylidene]-5-(1,1-dimethylethyl)-b-oxo-3-isoxazolepropanenitrile
- CBNumber
- CB12729362
- Molecular Formula
- C16H15ClN4O2
- Formula Weight
- 330.77
- MOL File
- 263707-16-0.mol
ESI 09 Property
- Melting point:
- >175°C (dec.)
- storage temp.
- 2-8°C
- solubility
- DMSO: soluble20mg/mL, clear
- form
- powder
- color
- , faint yellow to dark orange
- InChI
- InChI=1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-5-10(17)7-11/h4-8,19H,1-3H3/b20-13+
- InChIKey
- DXEATJQGQHDURZ-DEDYPNTBSA-N
- SMILES
- C(/C#N)(=N/NC1=CC=CC(Cl)=C1)\C(C1C=C(C(C)(C)C)ON=1)=O
Safety
- WGK Germany
- 3
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML0814
- Product name
- ESI-09
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $148.2
- Updated
- 2025/07/31
- Product number
- SML0814
- Product name
- ESI-09
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $621
- Updated
- 2025/07/31
- Product number
- 5.00506
- Product name
- EPAC Inhibitor, ESI-09
- Packaging
- 10 mg
- Price
- $243
- Updated
- 2025/07/31
- Product number
- 19130
- Product name
- ESI-09
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 19130
- Product name
- ESI-09
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $93
- Updated
- 2024/03/01
ESI 09 Chemical Properties,Usage,Production
Uses
ESI 09 acts as an EPAC inhibitor, preventing EPAC-mediated insulin release form β-pancreatic cells. Selective control for EPAC over PKA and decreases migration and invasion of AsPc-1 and PANC-1 pancreatic cancer cells.
Biochem/physiol Actions
ESI-09 is a potent, specific inhibitor of EPAC (exchange protein directly activated by cAMP). ESI-09 inhibits EPAC1 and EPAC2 with IC50 values of 3.2 and 1.4 μM, respectively, with no activity against PKA at 25 μM. In pancreatic cell lines, the compound blocks phosphorylation of Akt and insulin secretion. ESI-09 inhibits migration of pancreatic cancer cell lines.
Synthesis
1423915-00-7
108-42-9
263707-16-0
1. 3-Chloroaniline (30 mg, 0.24 mmol) was dissolved in 1 mL of cooled solvent at -5°C. 2. 0.24mL of 1N HCl (aq.) was added to the above solution to form an acidic aniline solution. 3. 1 mL of an aqueous solution of sodium nitrite (16 mg, 0.24 mmol) was added slowly and dropwise to the acidic aniline solution to form an aryl diazonium salt solution. 4. Sodium acetate (33 mg, 0.4 mmol) was added to the aryl diazonium salt solution, followed by the addition of 1 mL of crude 3-(5-tert-butylisoxazol-3-yl)-3-oxopropanenitrile (38 mg, 0.2 mmol) in ethanol. 5. The reaction mixture was stirred at 0 °C for 5 min, then poured into 10 mL of water and extracted with ethyl acetate (20 mL). 6. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. 7. The residue was purified by silica gel short column chromatography using hexane/ethyl acetate (2:1) as eluent to afford the target product 2-(5-(tert-butyl)isoxazol-3-yl)-N-(3-chlorophenyl)-2-oxoethylidenehydrazonium cyanide (40 mg, 61% yield) as a yellow solid with a melting point of 146-147 °C. The product was analyzed by HPLC. 8. HPLC analysis showed the product to be 99.6% pure (retention time fR = 21.72 min). 9. The structure of the product was confirmed by 1H NMR, 13C NMR and HRMS (ESI).
in vivo
Treatment with ESI-09 dramatically protects WT mice against R. australisinfection with much milder disease manifestations and significantly improves survival[2].
storage
Store at +4°C
References
[1] Tetrahedron Letters, 2013, vol. 54, # 12, p. 1546 - 1549
[2] Patent: WO2013/119931, 2013, A1. Location in patent: Paragraph 0214
ESI 09 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from ESI 09 manufacturers
- Product
- ESI 09 263707-16-0
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2019-07-09