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304909-07-7

304909-07-7 Structure

304909-07-7 Structure
IdentificationBack Directory
[Name]

SANT-1
[CAS]

304909-07-7
[Synonyms]

SANT-1
(E)-N-(4-benzylpiperazin-1-yl)-1-(3,5-dimethyl-1-phenylpyrazol-4-yl)methanimine
(4-Benzyl-piperazin-1-yl)-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethylene)-amine
N-[(3,5-DIMETHYL-1-PHENYL-1H-PYRAZOL-4-YL)METHYLENE]-4-(PHENYLMETHYL)-1-PIPERAZINAMINE
1-Piperazinamine, N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-(phenylmethyl)-
[Molecular Formula]

C23H27N5
[MDL Number]

MFCD01827306
[MOL File]

304909-07-7.mol
[Molecular Weight]

373.49
Chemical PropertiesBack Directory
[Appearance]

Pale Yellow Solid
[Melting point ]

104-106°C
[Boiling point ]

547.4±50.0 °C(Predicted)
[density ]

1.13±0.1 g/cm3(Predicted)
[storage temp. ]

−20°C
[solubility ]

Soluble in DMSO with warming
[form ]

White solid
[pka]

7.35±0.10(Predicted)
[Sensitive ]

Moisture & Light Sensitive
[CAS DataBase Reference]

304909-07-7
Hazard InformationBack Directory
[Chemical Properties]

Pale Yellow Solid
[Uses]

A potent antagonist of the sonic hedgehog (Shh) signaling pathway (IC50=20nm inShh-LIGHT2 assay an d in Ptch1-/- cells) that acts by binding to smoothened (Smo: KD=1.2 nM), a distant relative of G pro tein-coupled receptors. In contrast to cyclopamine, SNAT-1 inhibits the activities of both wild type and oncogenic Smo with equal potency (IC50=30nm in SmoA1-LIGHT2 assay).
[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).
[Description]

Smoothened (SMO) is a GPCR-like receptor which, with Patched, mediates hedgehog signaling to regulate gene expression through the Gli transcription factors. SANT 1 is a potent inhibitor of hedgehog signaling that acts by directly antagonizing SMO (IC50 = 20 nM). It counteracts SMO activation by the SMO agonist SAG but only partially competes with SAG binding to SMO. SANT 1 targets inactive SMO while it is in the cytoplasm, before it relocates to the primary cilium and is activated. Through antagonism of SMO, SANT 1 represses Gli-mediated transcription in a variety of cell types.
[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.
Safety DataBack Directory
[WGK Germany ]

3
Spectrum DetailBack Directory
[Spectrum Detail]

SANT-1(304909-07-7)1HNMR
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