Synonym
RK-20448; RK 20448; RK20448
IUPAC/Chemical Name
7-[cis-4-(4-methyl-1-piperazinyl)cyclohexyl]-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
InChi Key
FDVSOQRNTAPCHB-ZRZAMGCNSA-N
InChi Code
InChI=1S/C29H34N6O/c1-33-15-17-34(18-16-33)22-9-11-23(12-10-22)35-19-26(27-28(30)31-20-32-29(27)35)21-7-13-25(14-8-21)36-24-5-3-2-4-6-24/h2-8,13-14,19-20,22-23H,9-12,15-18H2,1H3,(H2,30,31,32)/t22-,23+
SMILES Code
NC1=C(C(C2=CC=C(OC3=CC=CC=C3)C=C2)=CN4[C@H]5CC[C@@H](N6CCN(C)CC6)CC5)C4=NC=N1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
RK-20448 is an ATP-competitive inhibitor of Lck, Src, KDR/VEGF2R, and Tie-2 (IC50s = 0.24, 1.19, 10.74, and 5.85 µM, respectively). It inhibits BLK, Csk, Fyn, and Lyn (IC50s = 0.37, 4.27, 2.03, and 0.43 µM, respectively). RK-20448 is the cis isomer of A-419259.
In vitro activity:
To be determined
In vivo activity:
RK-20448 inhibits TCR mediated IL-2 production in cellular and whole blood assays. Significantly, it is bioavailable and shows oral efficacy in mice after dosing in water vehicle.
Reference: Bioorg Med Chem Lett. 2002 Jun 17;12(12):1683-6. https://pubmed.ncbi.nlm.nih.gov/12039590/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
10.0 |
20.72 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
482.63
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Calderwood DJ, Johnston DN, Munschauer R, Rafferty P. Pyrrolo[2,3-d]pyrimidines containing diverse N-7 substituents as potent inhibitors of Lck. Bioorg Med Chem Lett. 2002 Jun 17;12(12):1683-6. doi: 10.1016/s0960-894x(02)00195-6. PMID: 12039590.
In vitro protocol:
To be determined
In vivo protocol:
1. Calderwood DJ, Johnston DN, Munschauer R, Rafferty P. Pyrrolo[2,3-d]pyrimidines containing diverse N-7 substituents as potent inhibitors of Lck. Bioorg Med Chem Lett. 2002 Jun 17;12(12):1683-6. doi: 10.1016/s0960-894x(02)00195-6. PMID: 12039590.
Saito, Y., Yuki, H., Kuratani, M., Hashizume, Y., Takagi, S., Honma, T., ... & Ishikawa, F. (2013). A pyrrolo-pyrimidine derivative targets human primary AML stem cells in vivo. Science translational medicine, 5(181), 181ra52-181ra52.
Almoyad, M. A. A., Alsayari, A., Wahab, S., & Chandra, S. (2024). Hematopoietic cell kinase as a nexus for drug repurposing: implications for cancer and HIV therapy. Journal of Biomolecular Structure and Dynamics, 1-11.
