- AC1NS4RE
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- $34.00
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2026-07-27
- CAS:1055412-47-9
- Purity: 99.72%
- Supply Ability: 10g
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| | 5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone Basic information |
| Product Name: | 5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone | | Synonyms: | (Z)-5-Chloro-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one;(Z)-SU5614;AC1NS4RE;(3Z)-5-Chloro-3-[(3,5-diMethyl-1H-pyrrol-2-yl)Methylene]-1,3-dihydro-2H-indol-2-one;SU 5614;SU-5614;CS-1552;5-chloro-3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylene]-1,3-dihydro-2 H-indol-2-one;2H-Indol-2-one, 5-chloro-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-, (3Z)- | | CAS: | 1055412-47-9 | | MF: | C15H13ClN2O | | MW: | 272.73 | | EINECS: | | | Product Categories: | Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pfizer compounds;Pharmaceuticals | | Mol File: | Mol File | ![5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone Structure](StructureFile/ChemBookStructure21/GIF/CB6459071.gif) |
| | 5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone Chemical Properties |
| Boiling point | 508.6±50.0 °C(Predicted) | | density | 1.352±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,2-8°C | | solubility | DMSO: ≥20mg/mL | | form | powder | | pka | 11.96±0.20(Predicted) | | color | orange | | InChI | 1S/C15H13ClN2O/c1-8-5-9(2)17-14(8)7-12-11-6-10(16)3-4-13(11)18-15(12)19/h3-7,17H,1-2H3,(H,18,19)/b12-7- | | InChIKey | XLBQNZICMYZIQT-GHXNOFRVSA-N | | SMILES | Cc1cc(C)c(\C=C2/C(=O)Nc3ccc(Cl)cc23)[nH]1 |
| Risk Statements | 53 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 4 |
| | 5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone Usage And Synthesis |
| Uses | SU5614 is a FMS-like tyrosine kinase 3 (FLT3) inhibitor; selective inhibitor of VEGF and PDGF receptor tyrosine kinases. | | Definition | ChEBI: SU5614 is a member of the class of oxindoles that is 5-chlorooxindole in which the two hydrogens at position 3 are replaced by a (3,5-dimethylpyrrol-2-yl)methylidene group. It has a role as a vascular endothelial growth factor receptor antagonist. It is a member of pyrroles, a member of oxindoles and an organochlorine compound. | | Biological Activity | su5614 is a protein tyrosine kinase inhibitor.tyrosine kinases are enzymes for the activation of many proteins by signal transduction cascades. the proteins are activated by adding a phosphate group to the protein. | | Synthesis | The general procedure for the synthesis of (Z)-5-chloro-3-((3,5-dimethyl-1H-pyrrol-2-ylidene)methylene)indolin-2-one from 3,5-dimethyl-2-pyrrolecarboxaldehyde and 5-chloroindole oxide was as follows: 5-chloroindole oxide (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g 41.6 mmol) and piperidine (410 μL, 4.16 mmol) were dissolved in 200 mL of ethanol and heated to reflux for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the solid was collected by filtration to afford the target product (Z)-5-chloro-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one (4.50 g, 40% yield) as a red to orange solid. | | in vitro | previous study found that su5614 could induce growth arrest and apoptosis in c-kit-expressing kasumi-1, m-07e, and ut-7 cells and inhibited the stem cell factor (scf)-induced tyrosine phosphorylation of c-kit. moreover, the sensitivity of kasumi-1 cells towards the growth inhibitory activity of su5614 was mainly caused by an autocrine production of scf, but not by the transforming mutations of c-kit [1]. | | in vivo | it was found that administration of su5614, a vascular endothelial growth factor (vegf) inhibitor, to mice could reduce the levels of vegf dramatically in bal fluids 72 h after toluene diisocyanate inhalation. moreover, consistent with the results obtained from the enzyme immunoassays, western blot analyses showed that su5614 reduced the levels of vegf in the bal fluid 72 h after toluene diisocyanate inhalation. these results suggested that vegf might be one of the major determinants of toluene diisocyanate -induced asthma and that the inhibition of vegf might be a good therapeutic strategy [2]. | | IC 50 | 100 nm for flt3 inhibition | | references | [1] spiekermann k,faber f,voswinckel r,hiddemann w. the protein tyrosine kinase inhibitor su5614 inhibits vegf-induced endothelial cell sprouting and induces growth arrest and apoptosis by inhibition of c-kit in aml cells. exp hematol.2002 jul;30(7):767-73.
[2] lee yc,kwak yg,song ch. contribution of vascular endothelial growth factor to airway hyperresponsiveness and inflammation in a murine model of toluene diisocyanate-induced asthma. j immunol.2002 apr 1;168(7):3595-600. |
| | 5-Chloro-3-[(3,5-dimethylpyrrol-2-yl)methylene]-2-indolinone Preparation Products And Raw materials |
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