304909-07-7

Basic information

• Product Name: SANT-1
• Synonyms: N-[(3,5-DIMETHYL-1-PHENYL-1H-PYRAZOL-4-YL)METHYLENE]-4-(PHENYLMETHYL)-1-PIPERAZINAMINE;SANT-1;(4-Benzyl-piperazin-1-yl)-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethylene)-amine;1-Piperazinamine, N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-(phenylmethyl)-;(E)-N-(4-benzylpiperazin-1-yl)-1-(3,5-dimethyl-1-phenylpyrazol-4-yl)methanimine
• CAS NO: 304909-07-7
• Molecular Formula: C₂₃H₂₇N₅
• Molecular Weight: 373.49
• Product Categories: All Inhibitors;Inhibitors;Lipid signaling
• Mol File: 304909-07-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 104-106°C
• Boiling Point: 547.4°Cat760mmHg
• Flash Point: 284.8°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO with warming
• PKA: 7.35±0.10(Predicted)
• Sensitive: Moisture & Light Sensitive
• CAS DataBase Reference: SANT-1(CAS DataBase Reference)
• NIST Chemistry Reference: SANT-1(304909-07-7)
• EPA Substance Registry System: SANT-1(304909-07-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 304909-07-7(Hazardous Substances Data)

Usage

Description

SANT-1 is a potent inhibitor of the hedgehog signaling pathway, acting as a direct antagonist of the Smoothened (SMO) receptor, a GPCR-like receptor. It targets the inactive form of SMO in the cytoplasm and represses Gli-mediated transcription in various cell types. SANT-1 is a pale yellow solid with an IC50 of 20 nM and a KD of 1.2 nM for SMO.

Uses

Used in Oncology:
SANT-1 is used as a therapeutic agent for treating Anaplastic lymphoma kinase (ALK)-positive anaplastic large cell lymphoma cells and chronic lymphocytic leukemia cells, inducing cell death in these cancerous cells.
Used in Smoothened (SMO) Inhibition:
SANT-1 is used as a potent antagonist of the sonic hedgehog (Shh) signaling pathway, binding to SMO with high affinity (KD=1.2 nM) and inhibiting its activity in both wild type and oncogenic forms with equal potency (IC50=30nm in SmoA1-LIGHT2 assay). This makes it a valuable tool in studying and modulating hedgehog signaling, which plays a crucial role in various developmental processes and diseases, including cancer.

Biological Activity

Potent, cell-permeable inhibitor of Sonic hedgehog (Shh) signaling; high affinity antagonist of smoothened activity (K D = 1.2 nM). Inhibits smoothened agonist effects with an IC 50 of 20 nM (in Shh-LIGHT2 cells).

Biochem/physiol Actions

SANT-1 is a potent sonic hedgehog pathway (Shh) antagonist that directly inhibits by binding to the smoothened (Smo) receptor. SANT-1 inhibits wild type and oncogenic Smo with equal potency.

references

[1]. chen j k., taipale j, young k e,. small molecule modulation of smoothened activity. proc natl acad sci u s a, 2002, 99: 14071-6.[2]. chun sg, zhou w & yee n s. combined targeting of histone deacetylases and hedgehog signaling enhances cytoxicity in pancreatic cancer. cancer biol ther, 2009, 8: 1328-39.

InChI:InChI=1/C23H27N5/c1-19-23(20(2)28(25-19)22-11-7-4-8-12-22)17-24-27-15-13-26(14-16-27)18-21-9-5-3-6-10-21/h3-12,17H,13-16,18H2,1-2H3/b24-17+

Downstream Products

• 39139-52-1 4-benzylpiperazin-1-amine