| Identification | Back Directory | [Name]
7-CYCLOPENTYL-5-(4-PHENOXY)PHENYL-7H-PYR | [CAS]
213743-31-8 | [Synonyms]
RK-24466
KIN 001-51
d]pyrimidin-4-ylamine
RK-24466 ;RK 24466 ;RK24466
7-CYCLOPENTYL-5-(4-PHENOXY)PHENYL-7H-PYR
Lck Inhibitor - CAS 213743-31-8 - Calbiochem
7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3‑
7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-cyclopentyl-5-(4-phenoxyphenyl)-
7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3‑:d]pyrimidin-4-ylamine | [Molecular Formula]
C23H22N4O | [MDL Number]
MFCD04974490 | [MOL File]
213743-31-8.mol | [Molecular Weight]
370.45 |
| Chemical Properties | Back Directory | [Boiling point ]
605.1±55.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 17 mg/mL at ≤60 °C, soluble
| [form ]
White solid | [pka]
5.75±0.30(Predicted) | [color ]
white
| [InChI]
1S/C23H22N4O/c24-22-21-20(14-27(17-6-4-5-7-17)23(21)26-15-25-22)16-10-12-19(13-11-16)28-18-8-2-1-3-9-18/h1-3,8-15,17H,4-7H2,(H2,24,25,26) | [InChIKey]
FMETVQKSDIOGPX-UHFFFAOYSA-N | [SMILES]
Nc1ncnc2n(cc(-c3ccc(Oc4ccccc4)cc3)c12)C5CCCC5 |
| Hazard Information | Back Directory | [Uses]
Lck Inhibitor is a cell-permeable ATP-competitive inhibitor of Lck. | [Definition]
ChEBI: RK-24466 is a member of the class of pyrrolopyrimidines that is 7H-pyrrolo[2,3-d]pyrimidine substituted by amino, 4-phenoxyphenyl, and cyclopentyl groups at positions 4, 5 and 7, respectively. It is a potent inhibitor of Lck that inhibits Lck (64-509) and LckCD isoforms (IC50 of less than 1 and 2 nM, respectively). It has a role as a geroprotector and an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor. It is a primary amino compound, a pyrrolopyrimidine, an aromatic amine, an aromatic ether and a member of cyclopentanes. | [General Description]
A cell-permeable pyrrolopyrimidine compound that acts as a potent, reversible, selective, and ATP-competitive inhibitor of Lck (IC50 at 5 μM ATP = <1 nM, 2 nM, 70 nM, 1.57 μM and 1.98 μM for lck64-509 Y394, Lckcd pY394, Src, Kdr and Tie-2, respectively; IC50 at 1 mM ATP = 16 μM, 66 nM, 126 nM, 420 nM and 5.18 μM for Lck64-509 Y394, Blk, Fyn, Lyn and Csk, respectively). Only minimally affects the activities of other kinases (IC50 = 3.2 μM, >33 μM, >50 μM and >50 μM for EGFR, PKC, CDC2/B and ZAP-70, respectively). Also shown to potently block T-cell receptor-stimulated IL-2 production in vitro (IC50<1-40 nM in Jurkat T cells) and in vivo (ED50 = 4 mg/kg in mice, ip.) | [Biochem/physiol Actions]
Primary TargetLck?????? Y3 | [in vivo]
RK-24466 inhibits T-cell receptor stimulated (a-CD3 mAb) IL-2 production in mice at low doses (ED50=4 mg/kg) after ip administration. However, efficacy is greatly reduced after oral administration (ED50=25 mg/kg) which is presumed to reflect poor intestinal absorption in the latter regimen. Inhibition of antigen specific T-cell immune responses is also seen for RK-24466. After administration of RK-24466 twice daily (100 mg/kg po) for 3 days during the in vivo priming phase, a 70% inhibition of IFNγ production is seen upon subsequent antigen-specific (KLH) challenge of lymphocytes from the draining lymph nodes in vitro[3]. RK-24466 suppresses the migration of VSMCs from endothelium-removed aortic rings, as well as neointima formation following rat carotid balloon injury[2]. |
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| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|