XRP44X - CAS 729605-21-4
Catalog number: 729605-21-4
Category: Inhibitor
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Molecular Formula:
C21H21ClN4O
Molecular Weight:
380.87
COA:
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Targets:
Microtubule/Tubulin
Description:
XRP44X, under the IUPAC name [4-(3-chlorophenyl)piperazin-1-yl]-(5-methyl-2-phenylpyrazol-3-yl)methanone, as an inhibitor of Tubulin it indirectly inhibits Net phosphorylation upstream of Erk1/2 activation. Ras-Net (Elk-3) pathway: IC50= 10 - 20 nM
Brife Description:
Inhibits microtubule polymerization
Synonyms:
[4-(3-chlorophenyl)piperazin-1-yl]-(5-methyl-2-phenylpyrazol-3-yl)methanone; XRP44X; 729605-21-4; 1-(3-CHLOROPHENYL)-4-[(3-METHYL-1-PHENYL-1H-PYRAZOL-5-YL)CARBONYL]PIPERAZINE; [4-(3-Chlorophenyl)-1-piperazinyl](3-methyl-1-phenyl-1H-pyrazol-5-yl)-methanone; 1-(3-Chlorophenyl)-4-((3-methyl-1-phenyl-1H-pyrazol-5-yl)carbonyl)piperazine; ACMC-20ejss; MLS006010688; SCHEMBL6259088; CHEMBL3184174; CTK5D7160; DTXSID20438402; NPHPNBGYPKBDDB-UHFFFAOYSA-N; ZINC3987355; MFCD12828749; AKOS024457429; TRA0076028; NCGC00346805-01; AK174344; CJ-11238; HE383857; KB-62004; SMR004701669(4-(3-chlorophenyl)piperazin-1-yl)(3-methyl-1-phenyl-1H-pyrazol-5-yl)methanone; [4-(3-chlorophenyl)piperazin-1-yl](5-methyl-2-phenyl-2H-pyrazol-3-yl)-methanone; [4-(3-Chlorophenyl)piperazin-1-yl](5-methyl-2-phenyl-2H-pyrazol-3-yl)methanone; PIPERAZINE, 1-(3-CHLOROPHENYL)-4-[(3-METHYL-1-PHENYL-1H-PYRAZOL-5-YL)CARBONYL]-; XRP44X|1-(3-Chlorophenyl)-4-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)carbonyl]piperazine
Solubility:
Soluble to 100 mM in DMSO and to 50 mM in ethanol
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -70℃ for long term (months to years).
MSDS:
Inquire
Density:
1.270 g/cm3
InChIKey:
NPHPNBGYPKBDDB-UHFFFAOYSA-N
InChI:
1S/C21H21ClN4O/c1-16-14-20(26(23-16)18-7-3-2-4-8-18)21(27)25-12-10-24(11-13-25)19-9-5-6-17(22)15-19/h2-9,14-15H,10-13H2,1H3
Canonical SMILES:
CC1=NN(C(=C1)C(=O)N2CCN(CC2)C3=CC(=CC=C3)Cl)C4=CC=CC=C4
1.Inhibition of the Ras-Net (Elk-3) pathway by a novel pyrazole that affects microtubules.
Wasylyk C;Zheng H;Castell C;Debussche L;Multon MC;Wasylyk B Cancer Res. 2008 Mar 1;68(5):1275-83. doi: 10.1158/0008-5472.CAN-07-2674.
Net (Elk-3/SAP-2/Erp) is a transcription factor that is phosphorylated and activated by the Ras-extracellular signal-regulated kinase (Erk) signaling pathway and is involved in wound healing, angiogenesis, and tumor growth. In a cell-based screen for small molecule inhibitors of Ras activation of Net transcriptional activity, we identified a novel pyrazole, XRP44X. XRP44X inhibits fibroblast growth factor 2 (FGF-2)-induced Net phosphorylation by the Ras-Erk signaling upstream from Ras. It also binds to the colchicine-binding site of tubulin, depolymerizes microtubules, stimulates cell membrane blebbing, and affects the morphology of the actin skeleton. Interestingly, Combretastin-A4, which produces similar effects on the cytoskeleton, also inhibits FGF-2 Ras-Net signaling. This differs from other classes of agents that target microtubules, which have either little effect (vincristine) or no effect (docetaxel and nocodazole) on the Ras-Net pathway. XRP44X inhibits various cellular properties, including cell growth, cell cycle progression, and aortal sprouting, similar to other molecules that bind to the tubulin colchicine site. XRP44X has the potentially interesting property of connecting two important pathways involved in cell transformation and may thereby represent an interesting class of molecules that could be developed for cancer treatment.
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CAS 729605-21-4 XRP44X

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